KR20200001861A - Novel Method for Preparing Xanthone Derivatives, Novel Xanthone Derivatives Made thereby, and Composition Comprising the Same - Google Patents

Abstract

The present invention relates to a method for manufacturing a novel xanthone derivative, the xanthone derivative manufactured therefrom, and use thereof. The method according to the present invention is a single step process without using a transition metal, so that synthesis proceeds efficiently even under mild reaction conditions and a compound comprising various substituents can also be stably synthesized. Therefore, xanthone derivatives manufactured by the same can exhibit excellent UV-filter characteristics, fluorescence sensing functions for Fe^3+, and antioxidant activity, thereby being able to be used in various ways.

Description

Novel Method for Preparing Xanthone Derivatives, Novel Xanthone Derivatives Made, and Composition Comprising the Same

The present invention relates to a novel method for producing a xanthone derivative, a novel xanthone derivative prepared therefrom, and a composition for detecting iron ions, a composition for blocking ultraviolet rays and an antioxidant composition comprising the same as an active ingredient.

N-tosylhydrazone compounds have been used as precursors or raw materials for diazo compounds for the last decade and have been used as starting materials and important building blocks in the field of organic synthesis. As a pioneering work, Barluenga, Valdes, and Wang developed new methods for the formation of C-C bonds, C-O bonds, C-N bonds, C-B bonds and C-Si bonds, starting from N-tosylhydrazone. Subsequently, cyclopropanation, CH insertion, ring expansion, coupling reaction, and heterocycle are synthesized using N-tosylhydrazone under a transition metal and a catalyst other than the transition metal. Reactions were developed. In addition, ring addition reactions between N-tosylhydrazone and electron deficient alkenes or alkyns have also been reported. For example, pyrazole derivatives are prepared upon reaction between N-tosylhydrazone and α, β-unsaturated carbonyl compounds such as cinnamic aldehyde under basic conditions.

As such, although good novel methods have been developed for the use of N-tosylhydrazone in the field of organic synthesis, there has been no report on the reaction of N-tosylhydrazone with 3-formylchromone. none.

Xanthone derivatives are heterocyclic compounds containing important oxygen found in many natural products that exhibit significant biological and pharmaceutical activity. Molecules containing xanthone backbones have potential anticancer activity, antibacterial activity, antimalarial activity, anticonvulsant activity, anticholinesterase activity, anti-HIV activity, antioxidant activity, antiangiogenic activity, anti-inflammatory activity, anti-Alzheimer's activity, protein kinase C activity, α-glucosidase activity and cholesterol acyltransferase inhibitor activity. Because of their importance and effects, various biosynthetic pathways and synthetic methods for synthesizing xanthone derivatives have been demonstrated. However, although various methods for synthesizing xanthones have been demonstrated, there is still a need for the development of simple and efficient methods for synthesizing more diverse and functional xanthone derivatives.

Korean Patent Registration No. 10-0819575 (registered on March 28, 2008).

It is an object of the present invention to provide novel xanthone derivatives exhibiting various activities.

Another object of the present invention is to provide a composition capable of effectively detecting trivalent iron ions (Fe ³⁺ ) and a kit comprising the same.

Still another object of the present invention is to provide a composition that can effectively block ultraviolet rays.

Another object of the present invention is to provide a composition exhibiting excellent antioxidant activity.

Another object of the present invention is to provide a method for preparing the novel xanthone derivative.

In order to achieve the above object, the present invention provides a xanthone derivative represented by Formula 1, or a pharmaceutically acceptable salt thereof:

[Formula 1]

In Formula 1, X is selected from the group consisting of substituted or unsubstituted aryl, heteroaryl, alkenyl and cycloalkenyl. R ¹ and R ² may be different or the same each and are selected from the group consisting of hydrogen, (C 1 -C 4) alkyl, (C 1 -C 3) alkoxy, and halogen, or R ¹ and R ² are linked to each other to benzene To form a ring, wherein the substituted aryl is one to three hydrogens in the aromatic ring substituted with one or more substituents selected from the group consisting of (C1-C4) alkyl, (C1-C3) alkoxy, and halogen .

The present invention also provides a composition or kit for detecting trivalent iron ions (Fe ³⁺ ) comprising an xanthone derivative represented by Chemical Formula 1, or a pharmaceutically acceptable salt thereof as an active ingredient.

Furthermore, the present invention provides a composition for protecting against ultraviolet rays, comprising an xanthone derivative represented by Formula 1, or a pharmaceutically acceptable salt thereof as an active ingredient.

In addition, the present invention provides a health functional food composition for antioxidant comprising a xanthone derivative represented by Formula 1, or a pharmaceutically acceptable salt thereof as an active ingredient.

The present invention also provides an antioxidant cosmetic composition comprising an xanthone derivative represented by Chemical Formula 1, or a pharmaceutically acceptable salt thereof as an active ingredient.

Furthermore, the present invention provides a method for preparing a xanthone derivative comprising reacting an N-tosylhydrazone derivative and a 3-formylchromone derivative at 70 ° C to 120 ° C in the presence of a base triethylamine (TEA). To provide.

According to the novel production method of the present invention, a condensation reaction of N-tosylhydrazone derivative and 4-oxo-4H-chromen-3-carbaaldehyde under mild base conditions is performed, thereby eliminating the need for a transition metal catalyst. Since the reaction can proceed, the production efficiency can be improved, the reaction time and cost can be reduced, and the xanthone derivatives including various substituents can be prepared. Since it exhibits iron ion detection activity and antioxidant activity, it can be usefully used in various compositions.

1 shows a reaction for obtaining a xanthone derivative upon reaction between a 3-formylchromone derivative and an N-tosylhydrazone derivative in the preparation method according to the present invention.
Figure 2 shows the mechanism for obtaining the xanthone derivative 3a according to the present invention.
3 is a result of confirming the UV blocking function of the xanthone derivatives according to the present invention.
4 is a result of confirming the trivalent iron ion sensing activity of the xanthone derivatives according to the present invention.

Hereinafter, the present invention will be described in more detail.

In this regard, the inventors of the present invention carried out the reaction of 3-formylchromone with N-tosylhydrazone under basic conditions to synthesize pyrazole derivatives, and through the first experiment under mild basic conditions , As shown in FIG. 1, it was confirmed that xanthone derivatives were produced instead of pyrazole derivatives, and thus, the present invention was completed.

Accordingly, the present invention provides a xanthone derivative represented by Formula 1, or a pharmaceutically acceptable salt thereof:

[Formula 1]

In Formula 1, X is selected from the group consisting of substituted or unsubstituted aryl, heteroaryl, alkenyl and cycloalkenyl. R ¹ and R ² may be different or the same each and are selected from the group consisting of hydrogen, (C 1 -C 4) alkyl, (C 1 -C 3) alkoxy, and halogen, or R ¹ and R ² are linked to each other to benzene To form a ring, wherein the substituted aryl is one to three hydrogens in the aromatic ring substituted with one or more substituents selected from the group consisting of (C1-C4) alkyl, (C1-C3) alkoxy, and halogen .

At this time, the reaction occurring during the preparation of the xanthone derivative is as shown in <Reaction Scheme 1>.

Scheme 1

Specifically, in Formula 1, X is phenyl unsubstituted or substituted with any one or more substituents selected from the group consisting of methyl, methoxy, bromo, and chloro; Naphthalenyl; Phenanthracenyl; Thiophenyl; Butylenyl; And cyclohexenyl, any one selected from the group consisting of R ¹ and R ² may be different or the same, and selected from the group consisting of hydrogen, methyl, isopropyl, methoxy, bromo, chloro, and fluoro; Alternatively, R ¹ and R ² may be connected to each other to form a benzene ring.

More specifically, the xanthone derivative is 2- (2-hydroxybenzoyl) -4-phenyl-9H-xanthene-9-one [2- (2-Hydroxybenzoyl) -4-phenyl-9H-xanthen-9-one ], 2- (2-hydroxy-5-methylbenzoyl) -7-methyl-4-phenyl-9H-xanthene-9-one [2- (2-Hydroxy-5-methylbenzoyl) -7-methyl-4- phenyl-9H-xanthen-9-one], 2- (2-hydroxy-5-isopropylbenzoyl) -7-isopropyl-4-phenyl-9H-xanthene-9-one [2- (2-Hydroxy- 5-isopropylbenzoyl) -7-isopropyl-4-phenyl-9H-xanthen-9-one, 2- (2-hydroxy-5-methoxybenzoyl) -7-methoxy-4-phenyl-9H-xanthene-9 -One [2- (2-Hydroxy-5-methoxybenzoyl) -7-methoxy-4-phenyl-9H-xanthen-9-one], 7-bromo-2- (5-bromo-2-hydroxybenzoyl ) -4-phenyl-9H-xanthene-9-one [7-Bromo-2- (5-bromo-2-hydroxybenzoyl) -4-phenyl-9H-xanthen-9-one], 7-chloro-2- ( 5-chloro-2-hydroxybenzoyl) -4-phenyl-9H-xanthene-9-one [7-Chloro-2- (5-chloro-2-hydroxybenzoyl) -4-phenyl-9H-xanthen-9-one ], 7-fluoro-2- (5-fluoro-2-hydroxybenzoyl) -4-phenyl-9H-xanthene-9-one [7-Fluoro-2- (5-fluoro-2-hydroxybenzoyl) -4-phenyl-9H-xanthen-9-one], 2-chloro-7- (5-chloro-2-hydroxy-4-methylbenzoyl) -3-methyl-5 -Phenyl-9H-xanthene-9-one [2-Chloro-7- (5-chloro-2-hydroxy-4-methylbenzoyl) -3-methyl-5-phenyl-9H-xanthen-9-one], 2- (5-Fluoro-2-hydroxybenzoyl) -7-methoxy-4-phenyl-9H-xanthene-9-one [2- (5-Fluoro-2-hydroxybenzoyl) -7-methoxy-4-phenyl- 9H-xanthen-9-one], 7-fluoro-2- (2-hydroxy-5-methoxybenzoyl) -4-phenyl-9H-xanthene-9-one [7-Fluoro-2- (2- hydroxy-5-methoxybenzoyl) -4-phenyl-9H-xanthen-9-one], 2- (2-hydroxybenzoyl) -4- (p-tolyl) -9H-xanthene-9-one [2- (2 -Hydroxybenzoyl) -4- (p-tolyl) -9H-xanthen-9-one], 4- (2,5-dimethylphenyl) -2- (2-hydroxybenzoyl) -9H-xanthene-9-one [ 4- (2,5-Dimethylphenyl) -2- (2-hydroxybenzoyl) -9H-xanthen-9-one], 2- (2-hydroxybenzoyl) -4- (3-methoxyphenyl) -9H-xanthene -9-one [2- (2-Hydroxybenzoyl) -4- (3-methoxyphenyl) -9H-xanthen-9-one], 4- (3,5-dimethoxyphenyl) -2- (2-hydroxybenzoyl ) -9H-Xanthene-9-one [4- (3,5-Dim ethoxyphenyl) -2- (2-hydroxybenzoyl) -9H-xanthen-9-one], 4- (2-bromophenyl) -2- (2-hydroxybenzoyl) -9H-xanthene-9-one [4- (2-Bromophenyl) -2- (2-hydroxybenzoyl) -9H-xanthen-9-one], 4- (2-chlorophenyl) -2- (2-hydroxybenzoyl) -9H-xanthene-9-one [ 4- (2-Chlorophenyl) -2- (2-hydroxybenzoyl) -9H-xanthen-9-one], 2- (2-hydroxybenzoyl) -4- (naphthalen-1-yl) -9H-xanthene-9 -One [2- (2-Hydroxybenzoyl) -4- (naphthalen-1-yl) -9H-xanthen-9-one], 2- (2-hydroxybenzoyl) -4- (naphthalen-2-yl)- 9H-Xanthene-9-one [2- (2-Hydroxybenzoyl) -4- (naphthalen-2-yl) -9H-xanthen-9-one], 2- (2-hydroxy-5-methylbenzoyl) -7 -Methyl-4- (naphthalen-1-yl) -9H-xanthen-9one [2- (2-Hydroxy-5-methylbenzoyl) -7-methyl-4- (naphthalen-1-yl) -9H-xanthen- 9-one], 2- (2-hydroxy-5-methoxybenzoyl) -7-methoxy-4- (naphthalen-1-yl) -9H-xanthene-9-one [2- (2-Hydroxy- 5-methoxybenzoyl) -7-methoxy-4- (naphthalen-1-yl) -9H-xanthen-9-one], 7-chloro-2- (5-chloro-2-hydroxybenzoyl) -4- (naphthalene -1-yl) -9H-xanthene-9- [7-Chloro-2- (5-chloro-2-hydroxybenzoyl) -4- (naphthalen-1-yl) -9H-xanthen-9-one], 2- (2-hydroxybenzoyl) -4- (phenan Tren-9-yl) -9H-xanthene-9-one [2- (2-Hydroxybenzoyl) -4- (phenanthren-9-yl) -9H-xanthen-9-one], 2- (2-hydroxybenzoyl ) -4- (thiophen-2-yl) -9H-xanthene-9-one [2- (2-Hydroxybenzoyl) -4- (thiophen-2-yl) -9H-xanthen-9-one], 9- (1-hydroxy-2-naphthoyl) -11- (p-tolyl) -7H-benzo [c] xanthene-7-one [9- (1-Hydroxy-2-naphthoyl) -11- (p-tolyl ) -7H-benzo [c] xanthen-7-one], 11- (2-bromophenyl) -9- (1-hydroxy-2-naphthoyl) -7H-benzo [c] xanthene-7-one [11- (2-Bromophenyl) -9- (1-hydroxy-2-naphthoyl) -7H-benzo [c] xanthen-7-one], 9- (1-hydroxy-2-naphthoyl) -11- (Naphthalen-1-yl) -7H-benzo [c] xanthene-7-one [9- (1-Hydroxy-2-naphthoyl) -11- (naphthalen-1-yl) -7H-benzo [c] xanthen- 7-one], 9- (1-hydroxy-2-naphthoyl) -11- (naphthalen-2-yl) -7H-benzo [c] xanthene-7-one [9- (1-Hydroxy-2- naphthoyl) -11- (naphthalen-2-yl) -7H-benzo [c] xanthen-7-one], 9- (1-hydroxy-2-naphthoyl) -11- (pe Tren-9-yl) -7H-benzo [c] xanthene-7-one [9- (1-Hydroxy-2-naphthoyl) -11- (phenanthren-9-yl) -7H-benzo [c] xanthen-7 -one], 2- (2-hydroxybenzoyl) -4- (2-methylprop-1-en-1-yl) -9H-xanthene-9-one [2- (2-Hydroxybenzoyl) -4- (2-methylprop-1-en-1-yl) -9H-xanthen-9-one], 9- (1-hydroxy-2-naphthoyl) -11- (2-methylprop-1-ene- 1-yl) -7H-benzo [c] xanthene-7-one [9- (1-Hydroxy-2-naphthoyl) -11- (2-methylprop-1-en-1-yl) -7H-benzo [c ] xanthen-7-one], 4- (cyclohex-2-en-1-yl) -2- (2-hydroxybenzoyl) -9H-xanthene-9-one [4- (Cyclohex-2-en- 1-yl) -2- (2-hydroxybenzoyl) -9H-xanthen-9-one], and 1- (benzylsulfonyl) -4-methylbenzene [1- (Benzylsulfonyl) -4-methylbenzene] Can be selected.

The compound represented by the formula (1) of the present invention can be used in the form of a pharmaceutically acceptable salt, such salts include metal salts formed by acid addition salts or bases formed by pharmaceutically acceptable free acids. There is this. An inorganic acid and an organic acid may be used as the free acid, and hydrochloric acid, sulfuric acid, bromic acid, sulfurous acid, or phosphoric acid may be used as the inorganic acid. The metal salts include alkali metal salts or alkaline earth metal salts, and sodium, potassium or calcium salts are useful.

In addition, the present invention provides a composition for detecting trivalent iron ions (Fe ³⁺ ) comprising a xanthone derivative represented by Formula 1 below, or a pharmaceutically acceptable salt thereof as an active ingredient:

[Formula 1]

In Formula 1, X is selected from the group consisting of substituted or unsubstituted aryl, heteroaryl, alkenyl and cycloalkenyl, R ¹ and R ² may be different or the same, respectively, hydrogen, (C1 ~ C4) Alkyl, (C 1 -C 3) alkoxy, and halogen, or R ¹ and R ² are connected to each other to form a benzene ring, wherein the substituted aryl is selected from one to three hydrogens of the aromatic ring. It is substituted with at least one substituent selected from the group consisting of (C1-C4) alkyl, (C1-C3) alkoxy, and halogen.

Specifically, in Formula 1, X is phenyl unsubstituted or substituted with any one or more substituents selected from the group consisting of methyl, methoxy, bromo, and chloro; Naphthalenyl; Phenanthracenyl; Thiophenyl; Butylenyl; And cyclohexenyl, any one selected from the group consisting of R ¹ and R ² may be different or the same, and selected from the group consisting of hydrogen, methyl, isopropyl, methoxy, bromo, chloro, and fluoro; Alternatively, R ¹ and R ² may be connected to each other to form a benzene ring.

More specifically, the xanthone derivative is 2- (2-hydroxybenzoyl) -4-phenyl-9H-xanthene-9-one [2- (2-Hydroxybenzoyl) -4-phenyl-9H-xanthen-9-one ], 2- (2-hydroxy-5-methylbenzoyl) -7-methyl-4-phenyl-9H-xanthene-9-one [2- (2-Hydroxy-5-methylbenzoyl) -7-methyl-4- phenyl-9H-xanthen-9-one], 2- (2-hydroxy-5-isopropylbenzoyl) -7-isopropyl-4-phenyl-9H-xanthene-9-one [2- (2-Hydroxy- 5-isopropylbenzoyl) -7-isopropyl-4-phenyl-9H-xanthen-9-one, 2- (2-hydroxy-5-methoxybenzoyl) -7-methoxy-4-phenyl-9H-xanthene-9 -One [2- (2-Hydroxy-5-methoxybenzoyl) -7-methoxy-4-phenyl-9H-xanthen-9-one], 7-bromo-2- (5-bromo-2-hydroxybenzoyl ) -4-phenyl-9H-xanthene-9-one [7-Bromo-2- (5-bromo-2-hydroxybenzoyl) -4-phenyl-9H-xanthen-9-one], 7-chloro-2- ( 5-chloro-2-hydroxybenzoyl) -4-phenyl-9H-xanthene-9-one [7-Chloro-2- (5-chloro-2-hydroxybenzoyl) -4-phenyl-9H-xanthen-9-one ], 7-fluoro-2- (5-fluoro-2-hydroxybenzoyl) -4-phenyl-9H-xanthene-9-one [7-Fluoro-2- (5-fluoro-2-hydroxybenzoyl) -4-phenyl-9H-xanthen-9-one], 2-chloro-7- (5-chloro-2-hydroxy-4-methylbenzoyl) -3-methyl-5 -Phenyl-9H-xanthene-9-one [2-Chloro-7- (5-chloro-2-hydroxy-4-methylbenzoyl) -3-methyl-5-phenyl-9H-xanthen-9-one], 2- (5-Fluoro-2-hydroxybenzoyl) -7-methoxy-4-phenyl-9H-xanthene-9-one [2- (5-Fluoro-2-hydroxybenzoyl) -7-methoxy-4-phenyl- 9H-xanthen-9-one], 7-fluoro-2- (2-hydroxy-5-methoxybenzoyl) -4-phenyl-9H-xanthene-9-one [7-Fluoro-2- (2- hydroxy-5-methoxybenzoyl) -4-phenyl-9H-xanthen-9-one], 2- (2-hydroxybenzoyl) -4- (p-tolyl) -9H-xanthene-9-one [2- (2 -Hydroxybenzoyl) -4- (p-tolyl) -9H-xanthen-9-one], 4- (2,5-dimethylphenyl) -2- (2-hydroxybenzoyl) -9H-xanthene-9-one [ 4- (2,5-Dimethylphenyl) -2- (2-hydroxybenzoyl) -9H-xanthen-9-one], 2- (2-hydroxybenzoyl) -4- (3-methoxyphenyl) -9H-xanthene -9-one [2- (2-Hydroxybenzoyl) -4- (3-methoxyphenyl) -9H-xanthen-9-one], 4- (3,5-dimethoxyphenyl) -2- (2-hydroxybenzoyl ) -9H-Xanthene-9-one [4- (3,5-Dim ethoxyphenyl) -2- (2-hydroxybenzoyl) -9H-xanthen-9-one], 4- (2-bromophenyl) -2- (2-hydroxybenzoyl) -9H-xanthene-9-one [4- (2-Bromophenyl) -2- (2-hydroxybenzoyl) -9H-xanthen-9-one], 4- (2-chlorophenyl) -2- (2-hydroxybenzoyl) -9H-xanthene-9-one [ 4- (2-Chlorophenyl) -2- (2-hydroxybenzoyl) -9H-xanthen-9-one], 2- (2-hydroxybenzoyl) -4- (naphthalen-1-yl) -9H-xanthene-9 -One [2- (2-Hydroxybenzoyl) -4- (naphthalen-1-yl) -9H-xanthen-9-one], 2- (2-hydroxybenzoyl) -4- (naphthalen-2-yl)- 9H-Xanthene-9-one [2- (2-Hydroxybenzoyl) -4- (naphthalen-2-yl) -9H-xanthen-9-one], 2- (2-hydroxy-5-methylbenzoyl) -7 -Methyl-4- (naphthalen-1-yl) -9H-xanthen-9one [2- (2-Hydroxy-5-methylbenzoyl) -7-methyl-4- (naphthalen-1-yl) -9H-xanthen- 9-one], 2- (2-hydroxy-5-methoxybenzoyl) -7-methoxy-4- (naphthalen-1-yl) -9H-xanthene-9-one [2- (2-Hydroxy- 5-methoxybenzoyl) -7-methoxy-4- (naphthalen-1-yl) -9H-xanthen-9-one], 7-chloro-2- (5-chloro-2-hydroxybenzoyl) -4- (naphthalene -1-yl) -9H-xanthene-9- [7-Chloro-2- (5-chloro-2-hydroxybenzoyl) -4- (naphthalen-1-yl) -9H-xanthen-9-one], 2- (2-hydroxybenzoyl) -4- (phenan Tren-9-yl) -9H-xanthene-9-one [2- (2-Hydroxybenzoyl) -4- (phenanthren-9-yl) -9H-xanthen-9-one], 2- (2-hydroxybenzoyl ) -4- (thiophen-2-yl) -9H-xanthene-9-one [2- (2-Hydroxybenzoyl) -4- (thiophen-2-yl) -9H-xanthen-9-one], 9- (1-hydroxy-2-naphthoyl) -11- (p-tolyl) -7H-benzo [c] xanthene-7-one [9- (1-Hydroxy-2-naphthoyl) -11- (p-tolyl ) -7H-benzo [c] xanthen-7-one], 11- (2-bromophenyl) -9- (1-hydroxy-2-naphthoyl) -7H-benzo [c] xanthene-7-one [11- (2-Bromophenyl) -9- (1-hydroxy-2-naphthoyl) -7H-benzo [c] xanthen-7-one], 9- (1-hydroxy-2-naphthoyl) -11- (Naphthalen-1-yl) -7H-benzo [c] xanthene-7-one [9- (1-Hydroxy-2-naphthoyl) -11- (naphthalen-1-yl) -7H-benzo [c] xanthen- 7-one], 9- (1-hydroxy-2-naphthoyl) -11- (naphthalen-2-yl) -7H-benzo [c] xanthene-7-one [9- (1-Hydroxy-2- naphthoyl) -11- (naphthalen-2-yl) -7H-benzo [c] xanthen-7-one], 9- (1-hydroxy-2-naphthoyl) -11- (pe Tren-9-yl) -7H-benzo [c] xanthene-7-one [9- (1-Hydroxy-2-naphthoyl) -11- (phenanthren-9-yl) -7H-benzo [c] xanthen-7 -one], 2- (2-hydroxybenzoyl) -4- (2-methylprop-1-en-1-yl) -9H-xanthene-9-one [2- (2-Hydroxybenzoyl) -4- (2-methylprop-1-en-1-yl) -9H-xanthen-9-one], 9- (1-hydroxy-2-naphthoyl) -11- (2-methylprop-1-ene- 1-yl) -7H-benzo [c] xanthene-7-one [9- (1-Hydroxy-2-naphthoyl) -11- (2-methylprop-1-en-1-yl) -7H-benzo [c ] xanthen-7-one], 4- (cyclohex-2-en-1-yl) -2- (2-hydroxybenzoyl) -9H-xanthene-9-one [4- (Cyclohex-2-en- 1-yl) -2- (2-hydroxybenzoyl) -9H-xanthen-9-one], and 1- (benzylsulfonyl) -4-methylbenzene [1- (Benzylsulfonyl) -4-methylbenzene] Can be selected.

In addition, the present invention provides a kit for detecting ^trivalent iron ions (Fe ^{3 +} ) comprising the composition as an active ingredient.

Furthermore, the present invention provides a composition for protecting against ultraviolet rays, comprising an xanthone derivative represented by Formula 1 below, or a pharmaceutically acceptable salt thereof as an active ingredient:

[Formula 1]

In Formula 1, X is selected from the group consisting of substituted or unsubstituted aryl, heteroaryl, alkenyl and cycloalkenyl, R ¹ and R ² may be different or the same, respectively, hydrogen, (C1 ~ C4) Alkyl, (C 1 -C 3) alkoxy, and halogen, or R ¹ and R ² are connected to each other to form a benzene ring, wherein the substituted aryl is selected from one to three hydrogens of the aromatic ring. It is substituted with at least one substituent selected from the group consisting of (C1-C4) alkyl, (C1-C3) alkoxy, and halogen.

Specifically, in Formula 1, X is phenyl unsubstituted or substituted with any one or more substituents selected from the group consisting of methyl, methoxy, bromo, and chloro; Naphthalenyl; Phenanthracenyl; Thiophenyl; Butylenyl; And cyclohexenyl, any one selected from the group consisting of R ¹ and R ² may be different or the same, and selected from the group consisting of hydrogen, methyl, isopropyl, methoxy, bromo, chloro, and fluoro; Alternatively, R ¹ and R ² may be connected to each other to form a benzene ring.

More specifically, the xanthone derivative is 2- (2-hydroxybenzoyl) -4-phenyl-9H-xanthene-9-one [2- (2-Hydroxybenzoyl) -4-phenyl-9H-xanthen-9-one ], 2- (2-hydroxy-5-methylbenzoyl) -7-methyl-4-phenyl-9H-xanthene-9-one [2- (2-Hydroxy-5-methylbenzoyl) -7-methyl-4- phenyl-9H-xanthen-9-one], 2- (2-hydroxy-5-isopropylbenzoyl) -7-isopropyl-4-phenyl-9H-xanthene-9-one [2- (2-Hydroxy- 5-isopropylbenzoyl) -7-isopropyl-4-phenyl-9H-xanthen-9-one, 2- (2-hydroxy-5-methoxybenzoyl) -7-methoxy-4-phenyl-9H-xanthene-9 -One [2- (2-Hydroxy-5-methoxybenzoyl) -7-methoxy-4-phenyl-9H-xanthen-9-one], 7-bromo-2- (5-bromo-2-hydroxybenzoyl ) -4-phenyl-9H-xanthene-9-one [7-Bromo-2- (5-bromo-2-hydroxybenzoyl) -4-phenyl-9H-xanthen-9-one], 7-chloro-2- ( 5-chloro-2-hydroxybenzoyl) -4-phenyl-9H-xanthene-9-one [7-Chloro-2- (5-chloro-2-hydroxybenzoyl) -4-phenyl-9H-xanthen-9-one ], 7-fluoro-2- (5-fluoro-2-hydroxybenzoyl) -4-phenyl-9H-xanthene-9-one [7-Fluoro-2- (5-fluoro-2-hydroxybenzoyl) -4-phenyl-9H-xanthen-9-one], 2-chloro-7- (5-chloro-2-hydroxy-4-methylbenzoyl) -3-methyl-5 -Phenyl-9H-xanthene-9-one [2-Chloro-7- (5-chloro-2-hydroxy-4-methylbenzoyl) -3-methyl-5-phenyl-9H-xanthen-9-one], 2- (5-Fluoro-2-hydroxybenzoyl) -7-methoxy-4-phenyl-9H-xanthene-9-one [2- (5-Fluoro-2-hydroxybenzoyl) -7-methoxy-4-phenyl- 9H-xanthen-9-one], 7-fluoro-2- (2-hydroxy-5-methoxybenzoyl) -4-phenyl-9H-xanthene-9-one [7-Fluoro-2- (2- hydroxy-5-methoxybenzoyl) -4-phenyl-9H-xanthen-9-one], 2- (2-hydroxybenzoyl) -4- (p-tolyl) -9H-xanthene-9-one [2- (2 -Hydroxybenzoyl) -4- (p-tolyl) -9H-xanthen-9-one], 4- (2,5-dimethylphenyl) -2- (2-hydroxybenzoyl) -9H-xanthene-9-one [ 4- (2,5-Dimethylphenyl) -2- (2-hydroxybenzoyl) -9H-xanthen-9-one], 2- (2-hydroxybenzoyl) -4- (3-methoxyphenyl) -9H-xanthene -9-one [2- (2-Hydroxybenzoyl) -4- (3-methoxyphenyl) -9H-xanthen-9-one], 4- (3,5-dimethoxyphenyl) -2- (2-hydroxybenzoyl ) -9H-Xanthene-9-one [4- (3,5-Dim ethoxyphenyl) -2- (2-hydroxybenzoyl) -9H-xanthen-9-one], 4- (2-bromophenyl) -2- (2-hydroxybenzoyl) -9H-xanthene-9-one [4- (2-Bromophenyl) -2- (2-hydroxybenzoyl) -9H-xanthen-9-one], 4- (2-chlorophenyl) -2- (2-hydroxybenzoyl) -9H-xanthene-9-one [ 4- (2-Chlorophenyl) -2- (2-hydroxybenzoyl) -9H-xanthen-9-one], 2- (2-hydroxybenzoyl) -4- (naphthalen-1-yl) -9H-xanthene-9 -One [2- (2-Hydroxybenzoyl) -4- (naphthalen-1-yl) -9H-xanthen-9-one], 2- (2-hydroxybenzoyl) -4- (naphthalen-2-yl)- 9H-Xanthene-9-one [2- (2-Hydroxybenzoyl) -4- (naphthalen-2-yl) -9H-xanthen-9-one], 2- (2-hydroxy-5-methylbenzoyl) -7 -Methyl-4- (naphthalen-1-yl) -9H-xanthen-9one [2- (2-Hydroxy-5-methylbenzoyl) -7-methyl-4- (naphthalen-1-yl) -9H-xanthen- 9-one], 2- (2-hydroxy-5-methoxybenzoyl) -7-methoxy-4- (naphthalen-1-yl) -9H-xanthene-9-one [2- (2-Hydroxy- 5-methoxybenzoyl) -7-methoxy-4- (naphthalen-1-yl) -9H-xanthen-9-one], 7-chloro-2- (5-chloro-2-hydroxybenzoyl) -4- (naphthalene -1-yl) -9H-xanthene-9- [7-Chloro-2- (5-chloro-2-hydroxybenzoyl) -4- (naphthalen-1-yl) -9H-xanthen-9-one], 2- (2-hydroxybenzoyl) -4- (phenan Tren-9-yl) -9H-xanthene-9-one [2- (2-Hydroxybenzoyl) -4- (phenanthren-9-yl) -9H-xanthen-9-one], 2- (2-hydroxybenzoyl ) -4- (thiophen-2-yl) -9H-xanthene-9-one [2- (2-Hydroxybenzoyl) -4- (thiophen-2-yl) -9H-xanthen-9-one], 9- (1-hydroxy-2-naphthoyl) -11- (p-tolyl) -7H-benzo [c] xanthene-7-one [9- (1-Hydroxy-2-naphthoyl) -11- (p-tolyl ) -7H-benzo [c] xanthen-7-one], 11- (2-bromophenyl) -9- (1-hydroxy-2-naphthoyl) -7H-benzo [c] xanthene-7-one [11- (2-Bromophenyl) -9- (1-hydroxy-2-naphthoyl) -7H-benzo [c] xanthen-7-one], 9- (1-hydroxy-2-naphthoyl) -11- (Naphthalen-1-yl) -7H-benzo [c] xanthene-7-one [9- (1-Hydroxy-2-naphthoyl) -11- (naphthalen-1-yl) -7H-benzo [c] xanthen- 7-one], 9- (1-hydroxy-2-naphthoyl) -11- (naphthalen-2-yl) -7H-benzo [c] xanthene-7-one [9- (1-Hydroxy-2- naphthoyl) -11- (naphthalen-2-yl) -7H-benzo [c] xanthen-7-one], 9- (1-hydroxy-2-naphthoyl) -11- (pe Tren-9-yl) -7H-benzo [c] xanthene-7-one [9- (1-Hydroxy-2-naphthoyl) -11- (phenanthren-9-yl) -7H-benzo [c] xanthen-7 -one], 2- (2-hydroxybenzoyl) -4- (2-methylprop-1-en-1-yl) -9H-xanthene-9-one [2- (2-Hydroxybenzoyl) -4- (2-methylprop-1-en-1-yl) -9H-xanthen-9-one], 9- (1-hydroxy-2-naphthoyl) -11- (2-methylprop-1-ene- 1-yl) -7H-benzo [c] xanthene-7-one [9- (1-Hydroxy-2-naphthoyl) -11- (2-methylprop-1-en-1-yl) -7H-benzo [c ] xanthen-7-one], 4- (cyclohex-2-en-1-yl) -2- (2-hydroxybenzoyl) -9H-xanthene-9-one [4- (Cyclohex-2-en- 1-yl) -2- (2-hydroxybenzoyl) -9H-xanthen-9-one], and 1- (benzylsulfonyl) -4-methylbenzene [1- (Benzylsulfonyl) -4-methylbenzene] Can be selected.

In this case, the UV blocking composition may be a cosmetic composition, but is not limited thereto.

In addition, the present invention provides a health functional food composition for antioxidant comprising a xanthone derivative represented by Formula 1 below, or a pharmaceutically acceptable salt thereof as an active ingredient:

[Formula 1]

In Formula 1, X is selected from the group consisting of substituted or unsubstituted aryl, heteroaryl, alkenyl and cycloalkenyl, R ¹ and R ² may be different or the same, respectively, hydrogen, (C1 ~ C4) Alkyl, (C 1 -C 3) alkoxy, and halogen, or R ¹ and R ² are connected to each other to form a benzene ring, wherein the substituted aryl is selected from one to three hydrogens of the aromatic ring. It is substituted with at least one substituent selected from the group consisting of (C1-C4) alkyl, (C1-C3) alkoxy, and halogen.

Specifically, in Formula 1, X is phenyl unsubstituted or substituted with any one or more substituents selected from the group consisting of methyl, methoxy, bromo, and chloro; Naphthalenyl; Phenanthracenyl; Thiophenyl; Butylenyl; And cyclohexenyl, any one selected from the group consisting of R ¹ and R ² may be different or the same, and selected from the group consisting of hydrogen, methyl, isopropyl, methoxy, bromo, chloro, and fluoro; Alternatively, R ¹ and R ² may be connected to each other to form a benzene ring.

More specifically, the xanthone derivative is 2- (2-hydroxybenzoyl) -4-phenyl-9H-xanthene-9-one [2- (2-Hydroxybenzoyl) -4-phenyl-9H-xanthen-9-one ], 2- (2-hydroxy-5-methylbenzoyl) -7-methyl-4-phenyl-9H-xanthene-9-one [2- (2-Hydroxy-5-methylbenzoyl) -7-methyl-4- phenyl-9H-xanthen-9-one], 2- (2-hydroxy-5-isopropylbenzoyl) -7-isopropyl-4-phenyl-9H-xanthene-9-one [2- (2-Hydroxy- 5-isopropylbenzoyl) -7-isopropyl-4-phenyl-9H-xanthen-9-one, 2- (2-hydroxy-5-methoxybenzoyl) -7-methoxy-4-phenyl-9H-xanthene-9 -One [2- (2-Hydroxy-5-methoxybenzoyl) -7-methoxy-4-phenyl-9H-xanthen-9-one], 7-bromo-2- (5-bromo-2-hydroxybenzoyl ) -4-phenyl-9H-xanthene-9-one [7-Bromo-2- (5-bromo-2-hydroxybenzoyl) -4-phenyl-9H-xanthen-9-one], 7-chloro-2- ( 5-chloro-2-hydroxybenzoyl) -4-phenyl-9H-xanthene-9-one [7-Chloro-2- (5-chloro-2-hydroxybenzoyl) -4-phenyl-9H-xanthen-9-one ], 7-fluoro-2- (5-fluoro-2-hydroxybenzoyl) -4-phenyl-9H-xanthene-9-one [7-Fluoro-2- (5-fluoro-2-hydroxybenzoyl) -4-phenyl-9H-xanthen-9-one], 2-chloro-7- (5-chloro-2-hydroxy-4-methylbenzoyl) -3-methyl-5 -Phenyl-9H-xanthene-9-one [2-Chloro-7- (5-chloro-2-hydroxy-4-methylbenzoyl) -3-methyl-5-phenyl-9H-xanthen-9-one], 2- (5-Fluoro-2-hydroxybenzoyl) -7-methoxy-4-phenyl-9H-xanthene-9-one [2- (5-Fluoro-2-hydroxybenzoyl) -7-methoxy-4-phenyl- 9H-xanthen-9-one], 7-fluoro-2- (2-hydroxy-5-methoxybenzoyl) -4-phenyl-9H-xanthene-9-one [7-Fluoro-2- (2- hydroxy-5-methoxybenzoyl) -4-phenyl-9H-xanthen-9-one], 2- (2-hydroxybenzoyl) -4- (p-tolyl) -9H-xanthene-9-one [2- (2 -Hydroxybenzoyl) -4- (p-tolyl) -9H-xanthen-9-one], 4- (2,5-dimethylphenyl) -2- (2-hydroxybenzoyl) -9H-xanthene-9-one [ 4- (2,5-Dimethylphenyl) -2- (2-hydroxybenzoyl) -9H-xanthen-9-one], 2- (2-hydroxybenzoyl) -4- (3-methoxyphenyl) -9H-xanthene -9-one [2- (2-Hydroxybenzoyl) -4- (3-methoxyphenyl) -9H-xanthen-9-one], 4- (3,5-dimethoxyphenyl) -2- (2-hydroxybenzoyl ) -9H-Xanthene-9-one [4- (3,5-Dim ethoxyphenyl) -2- (2-hydroxybenzoyl) -9H-xanthen-9-one], 4- (2-bromophenyl) -2- (2-hydroxybenzoyl) -9H-xanthene-9-one [4- (2-Bromophenyl) -2- (2-hydroxybenzoyl) -9H-xanthen-9-one], 4- (2-chlorophenyl) -2- (2-hydroxybenzoyl) -9H-xanthene-9-one [ 4- (2-Chlorophenyl) -2- (2-hydroxybenzoyl) -9H-xanthen-9-one], 2- (2-hydroxybenzoyl) -4- (naphthalen-1-yl) -9H-xanthene-9 -One [2- (2-Hydroxybenzoyl) -4- (naphthalen-1-yl) -9H-xanthen-9-one], 2- (2-hydroxybenzoyl) -4- (naphthalen-2-yl)- 9H-Xanthene-9-one [2- (2-Hydroxybenzoyl) -4- (naphthalen-2-yl) -9H-xanthen-9-one], 2- (2-hydroxy-5-methylbenzoyl) -7 -Methyl-4- (naphthalen-1-yl) -9H-xanthen-9one [2- (2-Hydroxy-5-methylbenzoyl) -7-methyl-4- (naphthalen-1-yl) -9H-xanthen- 9-one], 2- (2-hydroxy-5-methoxybenzoyl) -7-methoxy-4- (naphthalen-1-yl) -9H-xanthene-9-one [2- (2-Hydroxy- 5-methoxybenzoyl) -7-methoxy-4- (naphthalen-1-yl) -9H-xanthen-9-one], 7-chloro-2- (5-chloro-2-hydroxybenzoyl) -4- (naphthalene -1-yl) -9H-xanthene-9- [7-Chloro-2- (5-chloro-2-hydroxybenzoyl) -4- (naphthalen-1-yl) -9H-xanthen-9-one], 2- (2-hydroxybenzoyl) -4- (phenan Tren-9-yl) -9H-xanthene-9-one [2- (2-Hydroxybenzoyl) -4- (phenanthren-9-yl) -9H-xanthen-9-one], 2- (2-hydroxybenzoyl ) -4- (thiophen-2-yl) -9H-xanthene-9-one [2- (2-Hydroxybenzoyl) -4- (thiophen-2-yl) -9H-xanthen-9-one], 9- (1-hydroxy-2-naphthoyl) -11- (p-tolyl) -7H-benzo [c] xanthene-7-one [9- (1-Hydroxy-2-naphthoyl) -11- (p-tolyl ) -7H-benzo [c] xanthen-7-one], 11- (2-bromophenyl) -9- (1-hydroxy-2-naphthoyl) -7H-benzo [c] xanthene-7-one [11- (2-Bromophenyl) -9- (1-hydroxy-2-naphthoyl) -7H-benzo [c] xanthen-7-one], 9- (1-hydroxy-2-naphthoyl) -11- (Naphthalen-1-yl) -7H-benzo [c] xanthene-7-one [9- (1-Hydroxy-2-naphthoyl) -11- (naphthalen-1-yl) -7H-benzo [c] xanthen- 7-one], 9- (1-hydroxy-2-naphthoyl) -11- (naphthalen-2-yl) -7H-benzo [c] xanthene-7-one [9- (1-Hydroxy-2- naphthoyl) -11- (naphthalen-2-yl) -7H-benzo [c] xanthen-7-one], 9- (1-hydroxy-2-naphthoyl) -11- (pe Tren-9-yl) -7H-benzo [c] xanthene-7-one [9- (1-Hydroxy-2-naphthoyl) -11- (phenanthren-9-yl) -7H-benzo [c] xanthen-7 -one], 2- (2-hydroxybenzoyl) -4- (2-methylprop-1-en-1-yl) -9H-xanthene-9-one [2- (2-Hydroxybenzoyl) -4- (2-methylprop-1-en-1-yl) -9H-xanthen-9-one], 9- (1-hydroxy-2-naphthoyl) -11- (2-methylprop-1-ene- 1-yl) -7H-benzo [c] xanthene-7-one [9- (1-Hydroxy-2-naphthoyl) -11- (2-methylprop-1-en-1-yl) -7H-benzo [c ] xanthen-7-one], 4- (cyclohex-2-en-1-yl) -2- (2-hydroxybenzoyl) -9H-xanthene-9-one [4- (Cyclohex-2-en- 1-yl) -2- (2-hydroxybenzoyl) -9H-xanthen-9-one], and 1- (benzylsulfonyl) -4-methylbenzene [1- (Benzylsulfonyl) -4-methylbenzene] Can be selected.

The present invention also provides an antioxidant cosmetic composition comprising an xanthone derivative represented by Formula 1, or a pharmaceutically acceptable salt thereof as an active ingredient:

[Formula 1]

In Formula 1, X is selected from the group consisting of substituted or unsubstituted aryl, heteroaryl, alkenyl and cycloalkenyl, R ¹ and R ² may be different or the same, respectively, hydrogen, (C1 ~ C4) Alkyl, (C 1 -C 3) alkoxy, and halogen, or R ¹ and R ² are connected to each other to form a benzene ring, wherein the substituted aryl is selected from one to three hydrogens of the aromatic ring. It is substituted with at least one substituent selected from the group consisting of (C1-C4) alkyl, (C1-C3) alkoxy, and halogen.

Specifically, in Formula 1, X is phenyl unsubstituted or substituted with any one or more substituents selected from the group consisting of methyl, methoxy, bromo, and chloro; Naphthalenyl; Phenanthracenyl; Thiophenyl; Butylenyl; And cyclohexenyl, any one selected from the group consisting of R ¹ and R ² may be different or the same, and selected from the group consisting of hydrogen, methyl, isopropyl, methoxy, bromo, chloro, and fluoro; Alternatively, R ¹ and R ² may be connected to each other to form a benzene ring.

More specifically, the xanthone derivative is 2- (2-hydroxybenzoyl) -4-phenyl-9H-xanthene-9-one [2- (2-Hydroxybenzoyl) -4-phenyl-9H-xanthen-9-one ], 2- (2-hydroxy-5-methylbenzoyl) -7-methyl-4-phenyl-9H-xanthene-9-one [2- (2-Hydroxy-5-methylbenzoyl) -7-methyl-4- phenyl-9H-xanthen-9-one], 2- (2-hydroxy-5-isopropylbenzoyl) -7-isopropyl-4-phenyl-9H-xanthene-9-one [2- (2-Hydroxy- 5-isopropylbenzoyl) -7-isopropyl-4-phenyl-9H-xanthen-9-one, 2- (2-hydroxy-5-methoxybenzoyl) -7-methoxy-4-phenyl-9H-xanthene-9 -One [2- (2-Hydroxy-5-methoxybenzoyl) -7-methoxy-4-phenyl-9H-xanthen-9-one], 7-bromo-2- (5-bromo-2-hydroxybenzoyl ) -4-phenyl-9H-xanthene-9-one [7-Bromo-2- (5-bromo-2-hydroxybenzoyl) -4-phenyl-9H-xanthen-9-one], 7-chloro-2- ( 5-chloro-2-hydroxybenzoyl) -4-phenyl-9H-xanthene-9-one [7-Chloro-2- (5-chloro-2-hydroxybenzoyl) -4-phenyl-9H-xanthen-9-one ], 7-fluoro-2- (5-fluoro-2-hydroxybenzoyl) -4-phenyl-9H-xanthene-9-one [7-Fluoro-2- (5-fluoro-2-hydroxybenzoyl) -4-phenyl-9H-xanthen-9-one], 2-chloro-7- (5-chloro-2-hydroxy-4-methylbenzoyl) -3-methyl-5 -Phenyl-9H-xanthene-9-one [2-Chloro-7- (5-chloro-2-hydroxy-4-methylbenzoyl) -3-methyl-5-phenyl-9H-xanthen-9-one], 2- (5-Fluoro-2-hydroxybenzoyl) -7-methoxy-4-phenyl-9H-xanthene-9-one [2- (5-Fluoro-2-hydroxybenzoyl) -7-methoxy-4-phenyl- 9H-xanthen-9-one] 7-fluoro-2- (2-hydroxy-5-methoxybenzoyl) -4-phenyl-9H-xanthene-9-one [7-Fluoro-2- (2-hydroxy -5-methoxybenzoyl) -4-phenyl-9H-xanthen-9-one], 2- (2-hydroxybenzoyl) -4- (p-tolyl) -9H-xanthen-9-one [2- (2- Hydroxybenzoyl) -4- (p-tolyl) -9H-xanthen-9-one], 4- (2,5-dimethylphenyl) -2- (2-hydroxybenzoyl) -9H-xanthene-9-one [4 -(2,5-Dimethylphenyl) -2- (2-hydroxybenzoyl) -9H-xanthen-9-one], 2- (2-hydroxybenzoyl) -4- (3-methoxyphenyl) -9H-xanthene- 9-one [2- (2-Hydroxybenzoyl) -4- (3-methoxyphenyl) -9H-xanthen-9-one], 4- (3,5-dimethoxyphenyl) -2- (2-hydroxybenzoyl) -9H-xanthene-9-one [4- (3,5-Dime thoxyphenyl) -2- (2-hydroxybenzoyl) -9H-xanthen-9-one], 4- (2-bromophenyl) -2- (2-hydroxybenzoyl) -9H-xanthene-9-one [4- (2-Bromophenyl) -2- (2-hydroxybenzoyl) -9H-xanthen-9-one], 4- (2-chlorophenyl) -2- (2-hydroxybenzoyl) -9H-xanthene-9-one [ 4- (2-Chlorophenyl) -2- (2-hydroxybenzoyl) -9H-xanthen-9-one], 2- (2-hydroxybenzoyl) -4- (naphthalen-1-yl) -9H-xanthene-9 -One [2- (2-Hydroxybenzoyl) -4- (naphthalen-1-yl) -9H-xanthen-9-one], 2- (2-hydroxybenzoyl) -4- (naphthalen-2-yl)- 9H-Xanthene-9-one [2- (2-Hydroxybenzoyl) -4- (naphthalen-2-yl) -9H-xanthen-9-one], 2- (2-hydroxy-5-methylbenzoyl) -7 -Methyl-4- (naphthalen-1-yl) -9H-xanthen-9one [2- (2-Hydroxy-5-methylbenzoyl) -7-methyl-4- (naphthalen-1-yl) -9H-xanthen- 9-one], 2- (2-hydroxy-5-methoxybenzoyl) -7-methoxy-4- (naphthalen-1-yl) -9H-xanthene-9-one [2- (2-Hydroxy- 5-methoxybenzoyl) -7-methoxy-4- (naphthalen-1-yl) -9H-xanthen-9-one], 7-chloro-2- (5-chloro-2-hydroxybenzoyl) -4- (naphthalene -1-yl) -9H-xanthene-9-one [7-Chloro-2- (5-chloro-2-hydroxybenzoyl) -4- (naphthalen-1-yl) -9H-xanthen-9-one], 2- (2-hydroxybenzoyl) -4- (phenan Tren-9-yl) -9H-xanthene-9-one [2- (2-Hydroxybenzoyl) -4- (phenanthren-9-yl) -9H-xanthen-9-one], 2- (2-hydroxybenzoyl ) -4- (thiophen-2-yl) -9H-xanthene-9-one [2- (2-Hydroxybenzoyl) -4- (thiophen-2-yl) -9H-xanthen-9-one], 9- (1-hydroxy-2-naphthoyl) -11- (p-tolyl) -7H-benzo [c] xanthene-7-one [9- (1-Hydroxy-2-naphthoyl) -11- (p-tolyl ) -7H-benzo [c] xanthen-7-one], 11- (2-bromophenyl) -9- (1-hydroxy-2-naphthoyl) -7H-benzo [c] xanthene-7-one [11- (2-Bromophenyl) -9- (1-hydroxy-2-naphthoyl) -7H-benzo [c] xanthen-7-one], 9- (1-hydroxy-2-naphthoyl) -11- (Naphthalen-1-yl) -7H-benzo [c] xanthene-7-one [9- (1-Hydroxy-2-naphthoyl) -11- (naphthalen-1-yl) -7H-benzo [c] xanthen- 7-one], 9- (1-hydroxy-2-naphthoyl) -11- (naphthalen-2-yl) -7H-benzo [c] xanthene-7-one [9- (1-Hydroxy-2- naphthoyl) -11- (naphthalen-2-yl) -7H-benzo [c] xanthen-7-one], 9- (1-hydroxy-2-naphthoyl) -11- (pe Tren-9-yl) -7H-benzo [c] xanthene-7-one [9- (1-Hydroxy-2-naphthoyl) -11- (phenanthren-9-yl) -7H-benzo [c] xanthen-7 -one], 2- (2-hydroxybenzoyl) -4- (2-methylprop-1-en-1-yl) -9H-xanthene-9-one [2- (2-Hydroxybenzoyl) -4- (2-methylprop-1-en-1-yl) -9H-xanthen-9-one], 9- (1-hydroxy-2-naphthoyl) -11- (2-methylprop-1-ene- 1-yl) -7H-benzo [c] xanthene-7-one [9- (1-Hydroxy-2-naphthoyl) -11- (2-methylprop-1-en-1-yl) -7H-benzo [c ] xanthen-7-one], 4- (cyclohex-2-en-1-yl) -2- (2-hydroxybenzoyl) -9H-xanthene-9-one [4- (Cyclohex-2-en- 1-yl) -2- (2-hydroxybenzoyl) -9H-xanthen-9-one], and 1- (benzylsulfonyl) -4-methylbenzene [1- (Benzylsulfonyl) -4-methylbenzene] Can be selected.

Furthermore, the present invention provides a method for preparing a xanthone derivative comprising reacting an N-tosylhydrazone derivative and a 3-formylchromone derivative at 70 ° C to 120 ° C in the presence of a base TEA.

Preferably, the reaction may be performed using dimethyl sulfoxide (DMSO) as a solvent, it may be carried out at 90 ℃ to 120 ℃ for 2 to 4 hours.

In this case, the N-tosylhydrazone derivative may be represented by the following Formula 2:

[Formula 2]

In Formula 2, A is any one selected from the group consisting of substituted or unsubstituted aryl, heteroaryl, alkenyl and cycloalkenyl, wherein the substituted aryl is one to three hydrogen of the aromatic ring (C1 It may be substituted with any one or more substituents selected from the group consisting of -C4) alkyl, (C1-C3) alkoxy, and halogen.

Specifically, in the above formula, A is phenyl unsubstituted or substituted with any one or more substituents selected from the group consisting of methyl, methoxy, bromo, and chloro; Naphthalenyl; Phenanthracenyl; Thiophenyl; Butylenyl; And cyclohexenyl may be any one selected from the group consisting of.

In addition, the 3-formylchromone derivative may be represented by the following formula (3):

[Formula 3]

In Chemical Formula 3, B ¹ and B ² may be the same or different, respectively, and are substituted with a substituent selected from the group consisting of hydrogen, (C 1 -C 4) alkyl, (C 1 -C 3) alkoxy, and halogen, or B ¹ and B ² may be connected to each other to form a benzene ring.

Specifically, in Formula 3, B ¹ and B ² may be the same or different, and each one selected from the group consisting of hydrogen, methyl, isopropyl, methoxy, bromo, chloro, and fluoro, or , B ¹ and B ² may be connected to each other to form a benzene ring.

The xanthone derivative prepared through the above method may be represented by the following Formula 1.

[Formula 1]

In Formula 1, X is selected from the group consisting of substituted or unsubstituted aryl, heteroaryl, alkenyl and cycloalkenyl, R ¹ and R ² may be different or the same, respectively, hydrogen, (C1 ~ C4) Alkyl, (C 1 -C 3) alkoxy, and halogen, or R ¹ and R ² are connected to each other to form a benzene ring, wherein the substituted aryl is selected from one to three hydrogens of the aromatic ring. It is substituted with at least one substituent selected from the group consisting of (C1-C4) alkyl, (C1-C3) alkoxy, and halogen.

Specifically, in Formula 1, X is phenyl unsubstituted or substituted with any one or more substituents selected from the group consisting of methyl, methoxy, bromo, and chloro; Naphthalenyl; Phenanthracenyl; Thiophenyl; Butylenyl; And cyclohexenyl, any one selected from the group consisting of R ¹ and R ² may be different or the same, and selected from the group consisting of hydrogen, methyl, isopropyl, methoxy, bromo, chloro, and fluoro; Alternatively, R ¹ and R ² may be connected to each other to form a benzene ring.

More specifically, the xanthone derivative is 2- (2-hydroxybenzoyl) -4-phenyl-9H-xanthene-9-one [2- (2-Hydroxybenzoyl) -4-phenyl-9H-xanthen-9-one ], 2- (2-hydroxy-5-methylbenzoyl) -7-methyl-4-phenyl-9H-xanthene-9-one [2- (2-Hydroxy-5-methylbenzoyl) -7-methyl-4- phenyl-9H-xanthen-9-one], 2- (2-hydroxy-5-isopropylbenzoyl) -7-isopropyl-4-phenyl-9H-xanthene-9-one [2- (2-Hydroxy- 5-isopropylbenzoyl) -7-isopropyl-4-phenyl-9H-xanthen-9-one, 2- (2-hydroxy-5-methoxybenzoyl) -7-methoxy-4-phenyl-9H-xanthene-9 -One [2- (2-Hydroxy-5-methoxybenzoyl) -7-methoxy-4-phenyl-9H-xanthen-9-one], 7-bromo-2- (5-bromo-2-hydroxybenzoyl ) -4-phenyl-9H-xanthene-9-one [7-Bromo-2- (5-bromo-2-hydroxybenzoyl) -4-phenyl-9H-xanthen-9-one], 7-chloro-2- ( 5-chloro-2-hydroxybenzoyl) -4-phenyl-9H-xanthene-9-one [7-Chloro-2- (5-chloro-2-hydroxybenzoyl) -4-phenyl-9H-xanthen-9-one ], 7-fluoro-2- (5-fluoro-2-hydroxybenzoyl) -4-phenyl-9H-xanthene-9-one [7-Fluoro-2- (5-fluoro-2-hydroxybenzoyl) -4-phenyl-9H-xanthen-9-one], 2-chloro-7- (5-chloro-2-hydroxy-4-methylbenzoyl) -3-methyl-5 -Phenyl-9H-xanthene-9-one [2-Chloro-7- (5-chloro-2-hydroxy-4-methylbenzoyl) -3-methyl-5-phenyl-9H-xanthen-9-one], 2- (5-Fluoro-2-hydroxybenzoyl) -7-methoxy-4-phenyl-9H-xanthene-9-one [2- (5-Fluoro-2-hydroxybenzoyl) -7-methoxy-4-phenyl- 9H-xanthen-9-one] 7-fluoro-2- (2-hydroxy-5-methoxybenzoyl) -4-phenyl-9H-xanthene-9-one [7-Fluoro-2- (2-hydroxy -5-methoxybenzoyl) -4-phenyl-9H-xanthen-9-one], 2- (2-hydroxybenzoyl) -4- (p-tolyl) -9H-xanthen-9-one [2- (2- Hydroxybenzoyl) -4- (p-tolyl) -9H-xanthen-9-one], 4- (2,5-dimethylphenyl) -2- (2-hydroxybenzoyl) -9H-xanthene-9-one [4 -(2,5-Dimethylphenyl) -2- (2-hydroxybenzoyl) -9H-xanthen-9-one], 2- (2-hydroxybenzoyl) -4- (3-methoxyphenyl) -9H-xanthene- 9-one [2- (2-Hydroxybenzoyl) -4- (3-methoxyphenyl) -9H-xanthen-9-one], 4- (3,5-dimethoxyphenyl) -2- (2-hydroxybenzoyl) -9H-xanthene-9-one [4- (3,5-Dime thoxyphenyl) -2- (2-hydroxybenzoyl) -9H-xanthen-9-one], 4- (2-bromophenyl) -2- (2-hydroxybenzoyl) -9H-xanthene-9-one [4- (2-Bromophenyl) -2- (2-hydroxybenzoyl) -9H-xanthen-9-one], 4- (2-chlorophenyl) -2- (2-hydroxybenzoyl) -9H-xanthene-9-one [ 4- (2-Chlorophenyl) -2- (2-hydroxybenzoyl) -9H-xanthen-9-one], 2- (2-hydroxybenzoyl) -4- (naphthalen-1-yl) -9H-xanthene-9 -One [2- (2-Hydroxybenzoyl) -4- (naphthalen-1-yl) -9H-xanthen-9-one], 2- (2-hydroxybenzoyl) -4- (naphthalen-2-yl)- 9H-Xanthene-9-one [2- (2-Hydroxybenzoyl) -4- (naphthalen-2-yl) -9H-xanthen-9-one], 2- (2-hydroxy-5-methylbenzoyl) -7 -Methyl-4- (naphthalen-1-yl) -9H-xanthen-9one [2- (2-Hydroxy-5-methylbenzoyl) -7-methyl-4- (naphthalen-1-yl) -9H-xanthen- 9-one], 2- (2-hydroxy-5-methoxybenzoyl) -7-methoxy-4- (naphthalen-1-yl) -9H-xanthene-9-one [2- (2-Hydroxy- 5-methoxybenzoyl) -7-methoxy-4- (naphthalen-1-yl) -9H-xanthen-9-one], 7-chloro-2- (5-chloro-2-hydroxybenzoyl) -4- (naphthalene -1-yl) -9H-xanthene-9-one [7-Chloro-2- (5-chloro-2-hydroxybenzoyl) -4- (naphthalen-1-yl) -9H-xanthen-9-one], 2- (2-hydroxybenzoyl) -4- (phenan Tren-9-yl) -9H-xanthene-9-one [2- (2-Hydroxybenzoyl) -4- (phenanthren-9-yl) -9H-xanthen-9-one], 2- (2-hydroxybenzoyl ) -4- (thiophen-2-yl) -9H-xanthene-9-one [2- (2-Hydroxybenzoyl) -4- (thiophen-2-yl) -9H-xanthen-9-one], 9- (1-hydroxy-2-naphthoyl) -11- (p-tolyl) -7H-benzo [c] xanthene-7-one [9- (1-Hydroxy-2-naphthoyl) -11- (p-tolyl ) -7H-benzo [c] xanthen-7-one], 11- (2-bromophenyl) -9- (1-hydroxy-2-naphthoyl) -7H-benzo [c] xanthene-7-one [11- (2-Bromophenyl) -9- (1-hydroxy-2-naphthoyl) -7H-benzo [c] xanthen-7-one], 9- (1-hydroxy-2-naphthoyl) -11- (Naphthalen-1-yl) -7H-benzo [c] xanthene-7-one [9- (1-Hydroxy-2-naphthoyl) -11- (naphthalen-1-yl) -7H-benzo [c] xanthen- 7-one], 9- (1-hydroxy-2-naphthoyl) -11- (naphthalen-2-yl) -7H-benzo [c] xanthene-7-one [9- (1-Hydroxy-2- naphthoyl) -11- (naphthalen-2-yl) -7H-benzo [c] xanthen-7-one], 9- (1-hydroxy-2-naphthoyl) -11- (pe Tren-9-yl) -7H-benzo [c] xanthene-7-one [9- (1-Hydroxy-2-naphthoyl) -11- (phenanthren-9-yl) -7H-benzo [c] xanthen-7 -one], 2- (2-hydroxybenzoyl) -4- (2-methylprop-1-en-1-yl) -9H-xanthene-9-one [2- (2-Hydroxybenzoyl) -4- (2-methylprop-1-en-1-yl) -9H-xanthen-9-one], 9- (1-hydroxy-2-naphthoyl) -11- (2-methylprop-1-ene- 1-yl) -7H-benzo [c] xanthene-7-one [9- (1-Hydroxy-2-naphthoyl) -11- (2-methylprop-1-en-1-yl) -7H-benzo [c ] xanthen-7-one], 4- (cyclohex-2-en-1-yl) -2- (2-hydroxybenzoyl) -9H-xanthene-9-one [4- (Cyclohex-2-en- 1-yl) -2- (2-hydroxybenzoyl) -9H-xanthen-9-one], and 1- (benzylsulfonyl) -4-methylbenzene [1- (Benzylsulfonyl) -4-methylbenzene] Can be selected.

The cosmetic composition of the present invention may include conventionally acceptable ingredients in addition to the active ingredient, and may include, for example, conventional auxiliaries such as antioxidants, stabilizers, solubilizers, vitamins, pigments and flavors, and carriers.

Cosmetic compositions of the present invention may be prepared in any formulation conventionally prepared in the art and include, for example, solutions, suspensions, emulsions, pastes, gels, creams, lotions, powders, soaps, surfactant-containing cleansing , Oils, powder foundations, emulsion foundations, wax foundations and sprays, and the like, but are not limited thereto. More specifically, it may be prepared in the form of a flexible lotion (skin), nourishing lotion (milk lotion), nourishing cream, massage cream, essence, eye cream, cleansing cream, cleansing foam, cleansing water, pack, spray or powder. .

When the formulation of the present invention is a paste, cream or gel, animal oils, vegetable oils, waxes, paraffins, starches, trachants, cellulose derivatives, polyethylene glycols, silicones, bentonites, silicas, talc or zinc oxide may be used as carrier components. Can be.

When the formulation of the present invention is a powder or a spray, lactose, talc, silica, aluminum hydroxide, calcium silicate or polaramide powder may be used, in particular, in the case of a spray, additionally chlorofluorohydrocarbon, propane Propellant such as butane or dimethyl ether.

When the formulation of the present invention is a solution or emulsion, a solvent, solubilizing agent or emulsifying agent is used as a carrier component, for example water, ethanol, isopropanol, ethyl carbonate, ethyl acetate, benzyl alcohol, benzyl benzoate, propylene glycol, And fatty acid esters of 1,3-butylglycol oil, glycerol aliphatic ester, polyethylene glycol or sorbitan.

When the formulation of the present invention is a suspension, liquid carrier diluents such as water, ethanol or propylene glycol, suspending agents such as ethoxylated isostearyl alcohol, polyoxyethylene sorbitol esters and polyoxyethylene sorbitan esters, and microcrystals are used as carrier components. Soluble cellulose, aluminum metahydroxy, bentonite, agar or tracant and the like can be used.

When the formulation of the present invention is a surfactant-containing cleansing agent, the carrier component is an aliphatic alcohol sulfate, an aliphatic alcohol ether sulfate, a sulfosuccinic acid monoester, isethionate, an imidazolinium derivative, a methyltaurate, a sarcositate, a fatty acid amide. Ether sulfates, alkylamidobetaines, aliphatic alcohols, fatty acid glycerides, fatty acid diethanolamides, vegetable oils, lanolin derivatives or ethoxylated glycerol fatty acid esters and the like can be used.

The dietary supplement composition includes various nutrients, vitamins, minerals (electrolytes), flavors such as synthetic flavors and natural flavors, coloring and neutralizing agents (such as cheese and chocolate), pectic acid and salts thereof, alginic acid and salts thereof. , Organic acids, protective colloidal thickeners, pH adjusters, stabilizers, preservatives, glycerin, alcohols, carbonation agents used in carbonated drinks, and the like. Others may contain pulp for the production of natural fruit juices, synthetic fruit juices and vegetable drinks. These components can be used independently or in combination. In addition, the nutraceutical composition is in the form of meat, sausage, bread, chocolate, candy, snacks, confectionery, pizza, ramen, gum, ice cream, soup, beverages, tea, functional water, drinks, alcohol and vitamin complexes Can be.

In addition, the health functional food composition may further include a food additive, the suitability as a "food additive" is the item according to the General Regulations and General Test Methods of the Food Additives Code approved by the Food and Drug Administration unless otherwise specified It is determined by the standard and the standard.

Items listed in the "Food Additives Code" include, for example, chemical synthetic products such as ketones, glycine, potassium citrate, nicotinic acid, cinnamon acid, natural additives such as color pigments, licorice extract, crystalline cellulose, high-quench pigments, guar gum, L Mixed preparations, such as a sodium glutamate preparation, a noodles addition alkali agent, a preservative preparation, and a tar pigment preparation, etc. are mentioned.

At this time, the compound represented by the formula (1) or a pharmaceutically acceptable salt thereof according to the present invention added to the food in the process of preparing the health functional food composition may be appropriately added or reduced the content as necessary, preferably food It is preferred to add 100 parts by weight to include 1 to 15 parts by weight.

Hereinafter, examples will be described in detail to help understand the present invention. However, the following examples are provided to more fully explain the present invention to those skilled in the art, and the scope of the present invention is not limited to the following examples, only to illustrate the contents of the present invention. no.

Preparation Example Preparation of Reagent and Compound

All experiments according to the invention were carried out in contact with air. Various starting materials, N-tosylhydrazone derivatives (benzenesulfonohydrazide derivatives) and 3-formylchromone derivatives (chromen-3-carbaaldehyde), were purchased from Sigma-Aldrich. ^{Al 3 +, Ca 2 +,} Co 2 +, Cd 2 +, Cu 2 +, Fe 2 +, Fe 3 +, Hg 2 +, Pd 2 + and Zn ^{2 +} and the like were purchased from Sigma-Aldrich.

TLC for analysis was performed using a pre-coated silica gel plate (Art. 5554) with Merck's fluorescent indicator, and the melting point of each compound was determined using a Fisher-Johns melting point apparatus containing a micro-cover glass. Measured and not calibrated. ¹ H NMR analysis and ¹³ C NMR analysis was measured by using CDCl _3, DMSO-d ₆ and acetone-VNS Varian spectrometer at -d ₆ or DPX spectrometer (600 MHz and 300 MHz). IR analysis (infrared analysis) was recorded with a JASCO FTIR 5300 spectrophotometer, and high-resolution mass spectra were performed using a JOEL JMS-700 spectrometer (Korea Basic Science Institute).

Example 1 Optimization of Reaction Conditions

(1) optimization of reaction conditions

To find the optimum reaction conditions, (E) -N'-benzylidene-4-betaylbenzenesulfonohydrazide (1a) and 2 equivalents of 4-oxo-4H-chromen-3-carbaaldehyde (2a) The reaction was carried out under various base and solvent conditions as shown in Table 1 below.

([a] Reaction conditions: 1a 0.5 mmol and 2a 1 mmol per 5 mL of solvent, yield obtained after column chromatography [b])

In a first attempt conducted at 90 ° C. for 5 hours using DMSO as solvent, the inorganic base K ₂ CO ₃ (1 equiv) or Cs ₂ CO ₃ (1 equiv), compound 3a was 62% or 68%, respectively. Obtained in yields (entry 1 and 2). The yield of compound 3a did not change significantly (64%, entry 3) under KOH (1 equiv) condition, which is a strong base.

To increase the yield of this compound 3a, other organic bases were screened. First, DMSO as a solvent and 1 equivalent of TEA as a base were reacted at 90 ° C. for 3 hours, whereby compound 3a was produced at 83%, the highest yield (entry 4). Reducing the loading of TEA to 0.5 equivalents or increasing to 2 equivalents did not improve the yield of compound 3a (entry 5 and entry 6). In addition, experiments were conducted by using stronger bases DBU (1 equiv) and DABCO (1 equiv) to further improve the yield of compound 3a, but were unsuccessful (entry 7 and 8).

Then, experiments were conducted by changing the conditions of the solvent. When using other nonpolar and polar solvents such as toluene, THF, DMF, and ethanol, in addition to DMSO, Compound 3a was 31%, 55%, 62%, and 43%, respectively. Obtained in the yield of (entry 9 to 12). Moreover, the yield of compound 3a did not improve even when the reaction was carried out at low temperature (50 ° C.) or high temperature (120 ° C.) (entry 13 and 14).

The structure of Compound 3a thus obtained was analyzed through its spectral data, and the ¹ H NMR spectrum of Compound 3a was newly produced at δ8.65 (d, J = 1.8 Hz) and 8.11 ppm (d, J = 2.4 Hz). The broad singlet and two aromatic protons in the benzene ring showed a characteristic OH peak at δ 11.86 ppm, which appeared as a doublet peak due to the long range of coupling. In addition, ¹³ C NMR spectra showed peaks of carbon comprising two carbonyl and one hydroxy groups at δ 199.5, 176.7, and 163.3 ppm, respectively. The structure of compound 3a was demonstrated through single-crystal X-ray crystallographic analysis of structurally related compound 4c.

(2) generalization of the reaction

In order to further optimize the reaction as described above and to confirm the generality of the reaction to obtain various xanthone derivatives, as shown in <Reaction Scheme 2>, the compound 1a used above and the different 4-oxo-4H-chloro Xanthone derivatives (3b to 3g) were prepared by reacting men-3-carbaaldehyde compounds 2b to 2h.

Scheme 2

Reaction of compound 1a with 2b-2d comprising electron donor groups such as 6-methyl, 6-isopropyl and 6-methoxy yielded compounds 3b to 3d in yields of 85, 85, and 87%, respectively. In addition, in the reaction of 1a with 2e-2g containing an electron withdrawing group such as 6-bromo, 6-chloro and 6-fluoro, compounds 3e to 3g were each produced at a yield of 67-75%. Furthermore, upon reaction of 1h with 2h containing both the donor group and the electron withdrawal group, the desired reactant compound 3h was obtained with a yield of 79%.

These results maintain notable functional group tolerances and, when using 2b-2d, a 4-oxo-4H-chromen-3-carbaaldehyde derivative containing an electron donor group, are used as reactants containing an electron withdrawal group. It suggests that the desired product can be obtained with slightly higher yields than when using 2e-2g.

Based on these results, to confirm the range of reactants, various (E) -N'-benzylidene-4-methylbenzenesulfonohydrazide compounds 1b-1g and 4-oxo-4H-chromen-3-carba Aldehyde 2a was reacted through a reaction as shown in Scheme 3 below.

Scheme 3

Specifically, electron donor groups such as 4-methyl, 2,5-dimethyl, 3-methoxy and 3,5-dimethoxy in the benzene ring of compound 2a and benzylidene-4-methoxybenzenesulfonohydrazide In the reaction of 3b to 4 hours of compound 1b-1e comprising the desired compound 4a-4d was obtained in a yield range of 76 to 82%. In addition, the reaction of 2a with 1f-1g comprising electron withdrawal groups such as 2-bromo and 2-chloro in the benzene ring also successfully yielded compounds 4e and 4f in yields of 75% and 71%, respectively.

Therefore, this process provides a method for rapidly preparing various xanthone derivatives including various electron donor or electron withdrawal substituents in the benzene ring of the xanthone moiety.

(3) expansion of reaction

In order to confirm the versatility of the reaction as described above, by using various N-tosylhydrazone compounds including a polyaromatic ring and a heteroaromatic ring, a reaction as shown in <Reaction Scheme 4> is further conducted. Was performed.

Scheme 4

As a result, (Z) -4-methyl-N '-(naphthalen-1-ylmethylene) benzenesulfonohydrazide (1h) or (Z) -4-methyl-N'-(naphthalen-2-ylmethylene The reaction of benzenesulfonohydrazide (1i) with compound 2a produced compounds 5a and 5b in yields of 68% and 69%, respectively, while the reaction with compounds 1h and 2b, 2d, or 2f resulted in compounds 5c, 5d. And 5e in yields of 78%, 81%, and 74%, respectively. In addition, the reaction of (Z) -4-methyl-N '-(phenanthrene-9-ylmethylene) benzenesulfonohydrazide (1j) with 2a produced Compound 5 in a yield of 57%. In the reaction of) -4-methyl-N '-(thiophen-2-ylmethylene) benzenesulfonohydrazide (1k), 5 g of compound was produced in a yield of 48%.

Therefore, this reaction was confirmed to be a rapid synthesis method for preparing various xanthone derivatives including polyaromatic rings such as naphthalen-1-yl, naphthalen-2-yl, and phenanthracene-9-yl rings. In addition, the reaction was found to be effective in introducing a heteroaromatic ring such as a thiophen-2-yl group to a benzene ring of xanthone.

In addition, to expand the generality of the reaction, N-tosylhydrazone compounds 1b, 1f, 1h, 1i or 1j and 4-oxo-4H-benzo [h] chromen-3-carbaaldehyde (2i) The reaction was carried out as shown in Scheme 5.

Scheme 5

As a result, in the reaction with Compound 1b containing an electron donor group or 1f and 2i containing an electron donor group, Compounds 6a and 6b were produced at yields of 56% and 67%, respectively. In addition, compounds 1h, 1i and 1j containing polyaromatic rings and compound 2i were reacted to give compounds 6c, 6d and 6e in yields of 61%, 53% and 48%, respectively.

This protocol of benzannulation is not limited to only N-tosylhydrazone containing aryl or heteroaryl groups. As shown in <Scheme 6>, Compound 7a was obtained at 53% yield in the reaction between Compound 1l and 2a containing an alkenyl group, and Compound 7b was obtained at 56% yield in reaction with 1l and 2i. Similarly, even when 1m of compound containing 1-cyclohexenyl group and 2a were made to react, desired compound 7c was obtained by the yield of 46%.

Scheme 6

(4) Identification of substituent effect

To understand the substituent effect, as shown in Scheme 7 below, compound 1a and two other 4-oxo-4H-chromen-3-tabaaldehyde compounds each containing an electron donor group and an electron withdrawal group are 2d and 2g were allowed to compete.

Scheme 7

The reaction of 0.5 mmol of 1a compound with 1 mmol of 2d or 1 mmol of 2g gave compound 3d (19%) and 3g (31%), and also produced cross products 3i (9%) and 3j (20%). It became.

These results indicate that the fluoro group, which is an electron withdrawing group of 4-oxo-4H-chromen-3-carbaaldehyde, compared to 4-oxo-4H-chromen-3-carbaaldehyde containing a methoxy group, which is an electron donor group. This means that the substrate is made to show good Michael acceptor properties, and the reaction is made favorable.

(5) Identify mechanism

Then, a control experiment was conducted to identify the mechanism of the reaction, wherein the reactants, products, and reaction schemes were as shown in <Reaction Scheme 8>.

Scheme 8

In the presence of 1 equivalent of TEA contained in DMSO, the reaction proceeds for 30 minutes at 90 ° C. of compound 1a, resulting in a proton addition reaction to reaction intermediate 9 followed by a nucleophilic attack of reactive intermediate 11 of tosyl anion Compound 8 (68%) was obtained through diazo compound 10.

Based on the above results, as shown in FIG. 2, the valid mechanism of the compound 3a was elucidated.

That is, under basic conditions, N-tosylhydrazone compound 1a first generates diazo compound 10a, and compound 10b having a resonance structure of 10a undergoes a Michael addition reaction to compound 2a, followed by a retro-Michael reaction and a ring opening process. Form reaction intermediate 12. Under basic conditions, the deprotonation reaction of reaction intermediate 12 produces reaction intermediate 13, which reacts with another compound 2a molecule to produce reaction intermediate 14 via another Michael addition reaction. Subsequently, the intramolecular aldol reaction of reaction intermediate 14 produces intermediate 15, which undergoes removal of formic acid and denitrification, followed by deprotonation to yield 3a as a final product.

At this time, identification of formic acid by GC-MS targeting a mixture of reactions between 1a and 2a catalyzed by a base supports this reaction mechanism. As an application of this reaction, synthesized compounds were measured for their potential UV-filter properties, fluorescence sensors and antioxidant activity.

Example 2 Confirmation of Functionality of Xanthone Derivatives

(1) UV-filter characteristic check

First, 3a, 3b, 3c, 3h, 4e, 6a, 6b, 6e, and 7b of the xanthone derivative compounds prepared above were identified for UV absorption using UV and absorbed light at a given wavelength per molar concentration. Molecular extinction coefficient (ε), an important variable describing strength, was calculated using Beer-Lambert's law.

The result was as shown in FIG. In other words, according to previous reports, preconditions for the broad-spectrum UVA / UVB protection indications must be met when the critical wavelength is above 370 nm. The measured compounds 3a, 3b, 3c, 3h, and 4e have good UV- Filter characteristics were shown. Compounds 6a, 6b, 6e and 7b showed good UV-filter properties in the UVB region.

(2) Fe ³⁺  Check the Sensing Characteristics of Ions

Various organic molecules exhibiting toxicity, such as ^{Fe 3 +, Hg 2 +,} Pb 2 +, Cd 2 +, Cu 2 + has been applied to fluorescence detection of various metal ions. In order to check whether Fe ^{3 +} ions in the toxic metal ions can be monitored, fluorescence titration was performed on the derivative 6e prepared above.

Specifically, 1 mL of 6e (0.0001M) dissolved in 1,4-dioxane is placed in a 4 mL volume quartz cell and titrated using 0.25 mL (50 μM) of the above metal ions dissolved in water. It was. At this time, the control titration was performed using 0.25 mL of water without using metal ions. All fluorescence measurements were performed using Hitechi-7000 at room temperature and 355 nm (emission wavelength) after 5 min incubation at 240 nm / min scan rate conditions using a 5 nm slit width and 400 V photomultiplier tube. .

As a result, as shown in Figure 4, it was confirmed that the compound 6e exhibits the activity of selectively detecting the Fe ^{3 +} in particular.

(3) Antioxidant activity confirmation

Derivatives 5a-5e, 6c, and 7b prepared above were screened for antioxidant activity using the 1,1-diphenyl-2-picrylhydrazyl (DPPH) assay. DPPH is a stable free radical that is often used to investigate the free radical scavenging activity of antioxidants. First, compounds 5a-5e, 6c and 7b were evaluated and then compared to the standard concentrations of 25, 50, 75 and 100 μg mL ⁻¹ in BHT and ethanol. Half maximal inhibitory concentration (IC ₅₀ ), a measure of the effectiveness of compounds that inhibit DPPH free radicals by 50%, was calculated using a log dose-inhibition curve.

compound density( μg  mL ^-One )
(Free radical inhibition percentage) IC ₅₀
( μg  mL ^-One ) 100 75 50 25 5a 70.26 67.78 64.32 60.4 6.04 5b 69.53 64.12 61.88 59.44 6.87 5c 88.43 85.48 79.04 72.75 3.63 5d 81.96 77.24 73.47 67.32 4.76 5e 77.37 75.47 68.21 65.42 5.12 6c 79.2 74.67 70.87 65.75 4.94 7b 81.33 77.78 73.51 67.16 4.7 BHT 97.91 94.18 88.21 79.04 3.01

As a result, as shown in Table 2, 5c of the synthesized compounds had similar antioxidant activity (IC ₅₀ = 3.63 μg mL ^-1 ) to the antioxidant substance BHT (IC ₅₀ = 3.01 μg mL ^-1 ). ).

Synthesis Example Synthesis of Xanthone Derivative

1. Compound Analysis

All experiments according to the present invention were carried out in contact with air. TLC for analysis was performed using a pre-coated silica gel plate (Art 5554) with Merck's fluorescent indicator, to perform flash column chromatography. Silica gel 9385 (Merck) was used. The melting point of each compound was measured using a Fisher-Johns melting point apparatus with a micro-cover glass and not calibrated. ¹ H NMR analysis was performed at CDCl ₃ with a solvent chemical shift of 724 ppm and 0.00 ppm as reference. The solvent chemical shift of was recorded via a Varian-VNS (600 MHz) spectrometer in TMS. ¹³ C NMR spectra were measured using a Varian-VNS (150 MHz) spectrometer at 770 ppm CDCl ₃ as solvent chemical shift.

Chemical shifts (d) are expressed in ppm and J values are expressed in Hz.

Multiplicities are abbreviated as follows: s = singlet, d = doublet, t = triplet, q = quartet, br s = broad singlet, dd = doublet of double, td = triplet of double, quint = quintet, sept = septet and m = multiple terms.

IR analysis (infrared analysis) was recorded by FTIR (BIO-RAD), and high-resolution mass spectra were performed using JOEL JMS-700 spectrometer (Korea Basic Science Institute).

2. Synthesis Method

In an oven-dried two-necked flask, N-tosylhydrazone 1a (0.5 mmol), 4-oxo-4H-chromen-3-carbaaldehyde 2a (1 mmol), and TEA (1) in DMSO (5 mL) Equivalents) of the reaction mixture. After the reaction mixture was stirred vigorously at 90 ° C., the reaction process was monitored by TLC analysis. After the reaction was completed, the reaction mixture was cooled to room temperature.

The product was extracted twice with ethyl acetate (EtOAc) and the extracted solution was dried with anhydrous MgSO ₄ Dried over and filtered. The volatiles were removed in vacuo and the residue was purified by silica gel column chromatography (hexane: ethyl acetate = 19: 1) to afford the desired compound.

2-1. 2- (2- Hydroxybenzoyl ) -4-phenyl-9H- Xanten -9-one [2- (2- Hydroxybenzoyl ) -4-phenyl-9H- xanthen -9-one; 3a]

Compound 3a was obtained as a pale yellow solid according to the above synthesis method; Yield: 83% (162 mg). mp; 182-184 ° C. IR (ATR): 2949, 1592, 1451, 1297, 1220, 1145, 1094, 1008, 754, 694, 628 cm ⁻¹ . ¹ H NMR (600 MHz, CDCl ₃ ): d 11.87 (1H, s), 8.65 (1H, d, J = 1.8 Hz), 8.34 (1H, d, J = 7.2 Hz), 8.11 (1H, d, J = 2.4 Hz), 7.72 (1H, d, J = 7.8 Hz), 7.67 (3H, t, J = 7.8 Hz), 7.54-7.52 (3H, m), 7.46 (1H, t, J = 7.2 Hz), 7.44-7.40 (2H, m), 7.08 (1H, d, J = 9.0 Hz), 6.90 (1H, t, J = 7.2 Hz). ¹³ C NMR (150 MHz, CDCl ₃ ): d 199.5, 176.7, 163.3, 155.9, 155.0, 136.7, 135.9, 135.3, 135.2, 133.3, 133.2, 132.5, 129.6, 128.6, 128.5, 127.9, 126.8, 124.8, 121.6, 121.5, 119.1, 119.0, 118.6, 118.3. HRMS m / z (M ⁺ ): calcd for C ₂₆ H ₁₆ O ₄ : 392.1049; found: 392.1047.

2-2. 2- (2- Hydroxy -5- Methylbenzoyl ) -7- methyl -4-phenyl-9H- Xanten -9-one [2- (2- Hydroxy -5- methylbenzoyl ) -7-methyl-4-phenyl-9H-xanthen-9-one; 3b]

Compound 3b was obtained as a pale yellow solid according to the above synthesis method; Yield: 85% (178 mg); mp; 211-213 ° C. IR (ATR): 3031, 2924, 1814, 1625, 1393, 1295, 1220, 1126, 1036, 951, 707, 642, 526 cm ^-1 . ¹ H NMR (600 MHz, CDCl ₃ ): d 11.70 (1H, s), 8.66 (1H, d, J = 2.4 Hz), 8.14 (1H, s), 8.10 (1H, d, J = 1.8 Hz), 7.70 (2H, d, J = 6.6 Hz), 7.56-7.54 (3H, m), 7.49 (1H, t, J = 7.2 Hz), 7.45 (1H, s), 7.37-7.35 (2H, m), 7.01 (1H, d, J = 7.8 Hz), 2.48 (3H, s), 2.27 (3H, s). ¹³ C NMR (150 MHz, CDCl ₃ ): d 199.5, 176.8, 161.2, 155.0, 154.1, 137.7, 136.5, 135.6, 135.4, 134.7, 133.3, 132.9, 132.4, 129.6, 128.6, 128.4, 128.2, 127.8, 126.1, 121.5, 121.1, 118.7, 118.3, 118.0, 20.9, 20.6. HRMS m / z (M ⁺ ): calcd for C ₂₈ H ₂₀ O ₄ : 420. 1362; found: 420.1358.

2-3. 2- (2- Hydroxy -5- Isopropylbenzoyl ) -7-isopropyl-4-phenyl-9H- Xanten -9-one [2- (2- Hydroxy -5-isopropylbenzoyl) -7-isopropyl-4-phenyl-9H-xanthen-9-one; 3c]

Compound 3c was obtained as a white solid according to the above synthesis method. Yield: 84% (199 mg); mp; 161-163 ° C. IR (ATR): 2956, 1910, 1639, 1483, 1445, 1380, 1268, 1186, 1044, 913, 790, 706, 659, 586 cm ^-1 . ¹ H NMR (600 MHz, CDCl ₃ ): d 11.68 (1H, s), 8.69 (1H, d, J = 1.8 Hz), 8.19 (1H, d, J = 1.8 Hz), 8.13 (1H, d, J = 1.2 Hz), 7.68 (2H, d, J = 7.8 Hz), 7.60 (1H, dd, J = 9.0, 2.4 Hz), 7.54-7.52 (3H, m), 7.47 (1H, t, J = 7.2 Hz ), 7.43 (1H, dd, J = 8.4, 1.8 Hz), 7.37 (1H, d, J = 9.0 Hz), 7.03 (1H, d, J = 4.2 Hz), 3.08-3.01 (1H, m), 2.87 -2.80 (1H, m), 1.30 (6H, d, J = 3.6 Hz), 1.20 (6H, d, J = 3.3 Hz). ¹³ C NMR (150 MHz, CDCl ₃ ): d 199.4, 176.9, 161.4, 155.0, 154.3, 145.7, 139.3, 135.9, 135.5, 135.2, 134.3, 133.1, 132.4, 130.5, 129.6, 128.6, 128.4, 128.1, 123.5, 121.5, 121.2, 118.6, 118.4, 118.2, 33.7, 33.2, 24.0, 23.9. HRMS m / z (M ⁺ ): calcd for C ₃₂ H ₂₈ O ₄ : 476.1988; found: 476.1986.

2-4. 2- (2- Hydroxy -5- Methoxybenzoyl ) -7- Methoxy -4-phenyl-9H- Xanten -9-one [2- (2- Hydroxy -5-methoxybenzoyl) -7-methoxy-4-phenyl-9H-xanthen-9-one; 3d]

Compound 3d was obtained as a pale yellow solid according to the above synthesis method; Yield: 87% (196 mg); mp; 199-201 ° C. IR (ATR): 2939, 1694, 1638, 1479, 1275, 1213, 1160, 1022, 786, 710, 650, 548 cm ^-1 . ¹ H NMR (600 MHz, CDCl ₃ ): d 11.45 (1H, s), 8.71 (1H, d, J = 1.8 Hz), 8.12 (1H, d, J = 1.2 Hz), 7.69-7.66 (3H, m ), 7.53 (2H, t, J = 7.8 Hz), 7.47 (1H, t, J = 7.2 Hz), 7.38 (1H, d, J = 8.4 Hz), 7.33-7.31 (1H, m), 7.17 (1H , dd, J = 8.4, 3.0 Hz), 7.13 (1H, d, J = 2.4 Hz), 7.04 (1H, d, J = 8.4 Hz), 3.91 (3H, s), 3.70 (3H, s). ¹³ C NMR (150 MHz, CDCl ₃ ): d 199.0, 176.6, 157.6, 156.6, 155.0, 151.7, 150.1, 135.5, 135.3, 133.0, 132.5, 129.6, 128.6, 128.5, 127.9, 125.4, 124.7, 121.8, 121.0, 119.7, 119.5, 118.5, 115.6, 105.8, 56.0, 55.9. HRMS m / z (M ⁺ ): calcd for C ₂₈ H ₂₀ O ₆ : 452.1260; found: 452.1258.

2-5. 7- Bromo -2- (5- Bromo -2- Hydroxybenzoyl ) -4-phenyl-9H- Xanten -9-one [7- Bromo -2- (5- bromo -2-hydroxybenzoyl) -4-phenyl-9H-xanthen-9-one; 3e]

Compound 3e was obtained as a yellow solid according to the above synthesis method; Yield: 74% (201 mg); mp; 229-231 ° C. IR (ATR): 2917, 1751, 1454, 1345, 1281, 1208, 944, 830, 766, 689, 607, 520 cm ^-1 . ¹ H NMR (600 MHz, CDCl ₃ ): d 11.70 (1H, s), 8.61 (1H, d, J = 2.4 Hz), 8.47 (1H, d, J = 2.4 Hz), 8.08 (1H, d, J = 2.4 Hz), 7.81 (1H, dd, J = 8.4, 2.4 Hz), 7.73 (1H, d, J = 1.2 Hz), 7.65 (2H, d, J = 7.2 Hz), 7.61 (1H, dd, J = 9.0, 2.4 Hz), 7.54 (2H, t, J = 7.2 Hz), 7.49 (1H, t, J = 7.2 Hz), 7.34 (1H, d, J = 8.4 Hz), 7.01 (1H, d, J = 9.0 Hz). ¹³ C NMR (150 MHz, CDCl ₃ ): δ 198.4, 175.4, 162.1, 155.0, 154.6, 139.4, 138.2, 135.9, 135.0, 134.9, 133.1, 132.9, 129.6, 129.4, 128.7, 127.7, 122.7, 121.5, 120.7, 120.3, 120.2, 118.1, 110.7. HRMS m / z (M ⁺ ): calcd for C ₂₆ H ₁₄ Br ₂ O ₄ : 547.9259; found: 547.9258.

2-6. 7- Chloro -2- (5- Chloro -2- Hydroxybenzoyl ) -4-phenyl-9H- Xanten -9-one [7- Chloro -2- (5- chloro -2-hydroxybenzoyl) -4-phenyl-9H-xanthen-9-one; 3f]

Compound 3f was obtained as a pale yellow solid according to the above synthesis method; Yield: 69% (158 mg); mp; 229-231 ° C. IR (ATR): 2977, 1803, 1637, 1586, 1372, 1261, 1179, 1059, 956, 826, 580 cm ^-1 . ¹ H NMR (600 MHz, CDCl ₃ ): d 11.68 (1H, s), 8.60 (1H, d, J = 1.8 Hz), 8.29 (1H, d, J = 2.4 Hz), 8.08 (1H, d, J = 2.4 Hz), 7.67-7.64 (3H, m), 7.59 (1H, d, J = 2.4 Hz), 7.74 (2H, t, J = 7.2 Hz), 7.50-7.46 (2H, m), 7.40 (1H , d, J = 9.6 Hz), 7.05 (1H, d, J = 9.0 Hz). ¹³ C NMR (150 MHz, CDCl ₃ ): d 198.5, 175.5, 161.7, 155.0, 154.1, 136.7, 135.9, 135.5, 134.9, 133.0, 132.9, 132.0, 130.7, 129.6, 128.7, 127.6, 126.1, 123.8, 122.3, 121.4, 120.3, 120.1, 119.6. ^{HRMS m / z (M +)} : calcd for C 26 H 14 C l2 O 4: 460. 0269; found: 460. 0269.

2-7. 7- Fluoro -2- (5- Fluoro -2- Hydroxybenzoyl ) -4-phenyl-9H- Xanten -9-one [7- Fluoro -2- (5- fluoro -2-hydroxybenzoyl) -4-phenyl-9H-xanthen-9-one; 3 g]

Compound 3g was obtained as a white solid according to the above synthesis method; Yield: 67% (142 mg); mp; 219-221 ° C. IR (ATR): 3080, 1773, 1649, 1464, 1348, 1266, 1187, 978, 782, 685, 525 cm ^-1 . ¹ H NMR (600 MHz, CDCl ₃ ): d 11.55 (1H, s), 8.63 (1H, s), 8.10 (1H, s), 7.98 (1H, d, J = 7.2 Hz), 7.65 (2H, d , J = 7.2 Hz), 7.54 (2H, t, J = 7.2 Hz), 7.49 (1H, t, J = 7.2 Hz), 7.44 (2H, d, J = 6.0 Hz), 7.32 (1H, d, J = 9.0 Hz), 7.28 (1H, t, J = 7.8 Hz), 7.07 (1H, dd, J = 9.0, 4.2 Hz). ¹³ C NMR (150 MHz, CDCl ₃ ): d 198.5, 176.0, 159.4, 159.2 (d, J = 244.5 Hz), 155.3 (d, J = 61.5 Hz), 153.0 (d, J = 276 Hz), 135.8, 135.0, 133.0, 132.8, 129.6, 128.7, 128.6, 127.6, 124.4 (d, J = 24.0 Hz), 123.5 (d, J = 24.0 Hz), 122.4 (d, J = 7.5 Hz), 120.9, 120.4 (d, J = 7.5 Hz), 120.0 (d, J = 7.5 Hz), 118.4 (d, J = 24 Hz), 117.9 (d, J = 24.0 Hz) 111.7, 110.7 (d, J = 229.5 Hz). HRMS m / z (M ⁺ ): calcd for C ₂₆ H ₁₄ F ₂ O ₄ : 428. 0860; found: 428.0860.

2-8. 2- Chloro -7- (5- Chloro -2- Hydroxy -4- Methylbenzoyl ) -3- methyl -5-phenyl-9H- Xanten -9-on [2- Chloro -7- (5-chloro-2-hydroxy-4-methylbenzoyl) -3-methyl-5-phenyl-9H-xanthen-9-one; 3h]

Compound 3h was obtained as a light yellow solid according to the above synthesis method; Yield: 79% (192 mg); mp; 238-240 ° C. IR (ATR): 2927, 1599, 1448, 1353, 1239, 1141, 901, 784, 691, 589 cm ^-1 . ¹ H NMR (600 MHz, CDCl ₃ ): d 11.71 (1H, s), 8.59 (1H, d, J = 2.4 Hz), 8.28 (1H, s), 8.05 (1H, d, J = 2.4 Hz), 7.65-7.64 (2H, m), 7.58 (1H, s), 7.54 (2H, t, J = 7.2 Hz), 7.48 (1H, t, J = 6.6 Hz), 7.33 (1H, s), 6.98 (1H , s), 2.49 (3H, s), 2.40 (3H, s). ¹³ C NMR (150 MHz, CDCl ₃ ): d 198.2, 175.5, 161.6, 154.9, 154.1, 146.2, 144.9, 135.7, 135.1, 133.1, 132.7, 132.5, 131.4, 129.6, 128.7, 128.6, 127.5, 126.4, 124.5, 121.5, 120.6, 120.5, 120.1, 118.0, 21.0, 20.9. ^{HRMS m / z (M +)} : calcd for C 28 H 18 C l2 O 4: 488. 0582; found: 488. 0579.

2-9. 2- (5- Fluoro -2- Hydroxybenzoyl ) -7- Methoxy -4-phenyl-9H- Xanten -9-one [2- (5- Fluoro -2-hydroxybenzoyl) -7-methoxy-4-phenyl-9H-xanthen-9-one; 3i]

Compound 3i was obtained as a pale yellow solid according to the above synthesis method; Yield: 9% (19 mg); mp; 243-245 ° C. IR (ATR): 2926, 1659, 1521, 1403, 1300, 1233, 1984, 1027, 860, 692 cm ^-1 . ¹ H NMR (600 MHz, CDCl ₃ ): d 11.58 (1H, s), 8.66 (1H, d, J = 2.4 Hz), 8.08 (1H, d, J = 2.4 Hz), 7.70 (1H, d, J = 3.0 Hz), 7.67 (2H, d, J = 7.2 Hz), 7.54 (2H, t, J = 7.2 Hz), 7.48 (1H, t, J = 7.2 Hz), 7.39 (1H, d, J = 7.2 Hz), 7.35-7.32 (2H, m), 7.30-7.24 (1H, m), 7.08 (1H, dd, J = 8.4, 3.6 Hz), 3.92 (3H, s). ¹³ C NMR (150 MHz, CDCl ₃ ): d 198.7, 176.5, 159.4, 156.7, 155.1, 150.1, 135.3, 135.2, 132.6 (d, J = 19.5 Hz), 129.4 (d, J = 52.5 Hz), 128.6, 128.5, 127.8, 125.5, 124.3 (d, J = 24.0 Hz), 121.8, 121.1, 120.0, 119.9, 119.8, 118.6, 118.5, 118.0 (d, J = 24.0 Hz), 106.0, 56.0. HRMS m / z (M ⁺ ): calcd for C ₂₆ H ₁₄ F ₂ O ₄ : C ₂₇ H ₁₇ FO ₅ : 440. 1060; found: 440. 1058.

2-10. 7- Fluoro -2- (2- Hydroxy -5- Methoxybenzoyl ) -4-phenyl-9H- Xanten -9-one [7- Fluoro -2- (2- hydroxy -5-methoxybenzoyl) -4-phenyl-9H-xanthen-9-one; 3j]

Compound 3j was obtained as a pale yellow solid according to the above synthesis method; Yield: 20% (44 mg); mp; 187-189 ° C. IR (ATR): 2927, 1644, 1500, 1441, 1309, 1203, 1964, 948, 741 cm ^-1 . ¹ H NMR (600 MHz, CDCl ₃ ): d 11.41 (1H, s), 8.68 (1H, d, J = 2.4 Hz), 8.14 (1H, d, J = 2.4 Hz), 7.98-7.96 (1H, m ), 7.67-7.65 (2H, m), 7.54 (2H, t, J = 7.2 Hz), 7.50-7.47 (1H, m), 7.46-7.44 (2H, m), 7.17 (1H, dd, J = 9.0 , 3.0 Hz), 7.10 (1H, d, J = 7.1 Hz), 7.04 (1H, d, J = 7.0 Hz), 3.70 (3H, s). ¹³ C NMR (150 MHz, CDCl ₃ ): d 198.8, 176.0, 159.2 (d, J = 245.0 Hz), 157.6, 152.1, 151.7, 136.1, 135.1, 133.1 (d, J = 216 Hz), 129.6, 128.7, 128.6, 127.7, 124.7, 123.5 (d, J = 24 Hz), 122.4, 122.3, 120.8, 120.4, 120.3, 119.6, 118.4, 115.6, 111.6 (d, J = 22.5 Hz), 56.0. HRMS m / z (M ⁺ ): calcd for C ₂₇ H ₁₇ FO ₅ : 440. 1060; found: 440. 1062.

2-11. 2- (2- Hydroxybenzoyl ) -4- (p- Tolyl ) -9H- Xanten -9-one [2- (2- Hydroxybenzoyl ) -4- (p- tolyl ) -9H-xanthen-9-one; 4a]

Compound 4a was obtained as a pale yellow solid according to the above synthesis method; Yield: 82% (166 mg); mp; 171-173 ° C. IR (ATR): 2917, 1621, 1440, 1298, 1227, 1108, 1020, 939, 812, 749, 631, 559 cm ^-1 . ¹ H NMR (600 MHz, CDCl ₃ ): d 11.88 (1H, s), 8.62 (1H, s), 8.33 (1H, d, J = 8.4 Hz), 8.09 (1H, s), 7.71 (1H, t , J = 7.2 Hz), 7.66 (1H, d, J = 7.8 Hz), 7.57 (2H, d, J = 7.2 Hz), 7.53 (1H, t, J = 7.2), 7.44 (1H, d, J = 7.8 Hz), 7.40 (1H, t, J = 7.8 Hz), 7.34 (2H, d, J = 7.8 Hz), 7.08 (1H, d, J = 7.8 Hz), 6.90 (1H, t, J = 7.8 Hz ), 2.45 (3H, s). ¹³ C NMR (150 MHz, CDCl ₃ ): d 199.5, 176.7, 163.2, 155.8, 155.0, 138.4, 136.6, 135.7, 135.2, 133.3, 133.2, 132.4, 132.3, 129.5, 129.3, 127.6, 126.7, 124.7, 121.6, 121.4, 119.0, 118.9, 118.5, 118.3, 21.3. HRMS m / z (M ⁺ ): calcd for C ₂₇ H ₁₈ O ₄ : 406. 1205; found: 406. 1202.

2-12. 4- (2,5- Dimethylphenyl ) -2- (2- Hydroxybenzoyl ) -9H- Xanten -9-one [4- (2,5- Dimethylphenyl ) -2- (2-hydroxybenzoyl) -9H-xanthen-9-one; 4b]

Compound 4b was obtained as a light yellow solid according to the above synthesis method; Yield: 76% (159 mg); mp; 158-160 ° C. IR (ATR): 2920, 1621, 1441, 1391, 1300, 1233, 1121, 937, 747, 673, 564 cm ^-1 . ¹ H NMR (600 MHz, CDCl ₃ ): d 11.88 (1H, s), 8.69 (1H, d, J = 1.8 Hz), 8.34 (1H, dd, J = 7.8, 1.8 Hz), 7.99 (1H, d , J = 2.4 Hz), 7.70-7.68 (2H, m), 7.53 (1H, t, J = 7.8 Hz), 7.40 (1H, t, J = 7.2 Hz), 7.35 (1H, d, J = 8.4 Hz ), 7.24 (1H, t, J = 7.2 Hz), 7.20 (1H, d, J = 7.8 Hz), 7.13 (1H, s), 7.09 (1H, d, J = 9.0 Hz), 6.91 (1H, t , J = 8.4 Hz), 2.38 (3H, s), 2.16 (3H, s). ¹³ C NMR (150 MHz, CDCl ₃ ): d 199.4, 176.8, 163.2, 155.9, 155.3, 136.6, 136.3, 135.5, 135.3, 134.9, 133.6, 133.2, 133.1, 132.9, 130.9, 130.0, 129.4, 128.0, 127.0, 124.7, 121.5, 121.2, 119.0, 118.9, 118.6, 118.3, 20.9, 19.6. HRMS m / z (M ⁺ ): calcd for C ₂₈ H ₂₀ O ₄ : 420. 1362; found: 420. 1361.

2-13. 2- (2- Hydroxybenzoyl ) -4- (3- Methoxyphenyl ) -9H- Xanten -9-one [2- (2- Hydroxybenzoyl ) -4- (3-methoxyphenyl) -9H-xanthen-9-one; 4c]

Compound 4c was obtained as a white solid according to the above synthesis method. Yield: 78% (164 mg); mp; 176-178 ° C. IR (ATR): 2925, 1637, 1455, 1264, 1165, 1035, 878, 763, 693, 567 cm ^-1 . ¹ H NMR (600 MHz, CDCl ₃ ): d 11.81 (1H, s), 8.59 (1H, d, J = 1.8 Hz), 8.28 (1H, d, J = 7.8 Hz), 8.06 (1H, d, J = 1.8 Hz), 7.67 (1H, t, J = 7.2 Hz), 7.60 (1H, d, J = 7.8 Hz), 7.47 (1H, t, J = 6.6 Hz), 7.39-7.34 (3H, m), 7.18 (2H, t, J = 9.6 Hz), 7.03 (1H, d, J = 8.4 Hz), 6.97 (1H, dd, J = 9.0, 2.4 Hz), 6.85 (1H, t, J = 7.8 Hz), 3.82 (3 H, s). ¹³ C NMR (150 MHz, CDCl ₃ ): d 199.4, 176.7, 163.3, 159.7, 155.8, 155.0, 136.7, 136.5, 135.8, 135.3, 133.3, 133.2, 132.3, 129.6, 128.0, 126.8, 124.7, 122.0, 121.6, 121.5, 119.1, 118.9, 118.6, 118.3, 115.4, 114.0, 55.4. HRMS m / z (M ⁺ ): calcd for C ₂₇ H ₁₈ O ₅ : 422. 1154 found: 422. 1152.

2-14. 4- (3,5- Dimethoxyphenyl ) -2- (2- Hydroxybenzoyl ) -9H- Xanten -9-one [4- (3,5- Dimethoxyphenyl ) -2- (2-hydroxybenzoyl) -9H-xanthen-9-one; 4d]

Compound 4d was obtained as a white solid according to the above synthesis method. Yield: 77% (174 mg); mp; 169-171 ° C. IR (ATR): 2986, 2230, 1835, 1633, 1490, 1384, 1258, 1184, 1055, 920, 835, 591 cm ^-1 . ¹ H NMR (600 MHz, CDCl ₃ ): d 11.86 (1H, s), 8.65 (1H, d, J = 2.4 Hz), 8.35 (1H, dd, J = 7.2, 1.2 Hz), 8.12 (1H, d , J = 2.4 Hz), 7.73 (1H, t, J = 8.4 Hz), 7.66 (1H, dd, J = 7.8, 1.2 Hz), 7.54 (1H, t, J = 7.8 Hz), 7.46 (1H, d , J = 9.0 Hz), 7.42 (1H, t, J = 8.4 Hz), 7.09 (1H, d, J = 8.4 Hz), 6.90 (1H, t, J = 7.8 Hz), 6.80 (2H, t, J = 1.8 Hz), 6.58 (1H, t, J = 1.8 Hz), 3.85 (6H, s). ¹³ C NMR (150 MHz, CDCl ₃ ): d 199.4, 176.7, 163.3, 160.8, 155.9, 155.0, 137.1, 136.7, 135.7, 135.4, 133.3, 133.2, 132.4, 128.0, 126.8, 124.8, 121.6, 121.5, 119.1, 119.0, 118.6, 118.3, 107.9, 100.5, 55.5. HRMS m / z (M ⁺ ): calcd for C ₂₈ H ₂₀ O ₆ : 452. 1260; found: 452. 1260.

2-15. 4- (2- Bromophenyl ) -2- (2- Hydroxybenzoyl ) -9H- Xanten -9-one [4- (2- Bromophenyl ) -2- (2-hydroxybenzoyl) -9H-xanthen-9-one; 4e]

Compound 4e was obtained as a white solid according to the above synthesis method. Yield: 75% (176 mg); mp; 150-152 ° C. IR (ATR): 2977, 1664, 1456, 1264, 1305, 1217, 1017, 920, 743, 538 cm ^-1 . ¹ H NMR (600 MHz, CDCl ₃ ): d 11.84 (1H, s), 8.73 (1H, d, J = 1.8 Hz), 8.32 (1H, d, J = 7.8 Hz), 8.00 (1H, d, J = 7.8 Hz), 7.75 (1H, d, J = 7.8 Hz), 7.70-7.67 (2H, m), 7.52 (1H, t, J = 7.8 Hz), 7.47-7.42 (2H, m), 7.39 (1H , t, J = 7.8 Hz), 7.36-7.33 (2H, m), 7.07 (1H, d, J = 7.8 Hz), 6.91 (1H, t, J = 7.8 Hz). ¹³ C NMR (150 MHz, CDCl ₃ ): d 199.1, 176.6, 163.2, 155.8, 155.1, 136.6, 136.4, 136.3, 135.3, 133.3, 133.0, 132.9, 131.7, 131.6, 130.1, 128.7, 127.5, 126.7, 124.7, 124.0, 121.5, 121.4, 119.1, 118.9, 118.6, 118.3. HRMS m / z (M ⁺ ): calcd for C ₂₆ H ₁₅ BrO ₄ : 470. 0154; found: 470. 0155.

2-16. 4- (2- Chlorophenyl ) -2- (2- Hydroxybenzoyl ) -9H- Xanten -9-one [4- (2- Chlororophenyl ) -2- (2-hydroxybenzoyl) -9H-xanthen-9-one; 4f]

Compound 4f was obtained as a yellow solid according to the above synthesis method; Yield: 71% (151 mg); mp; 165-167 ° C. IR (ATR): 2929, 1720, 1446, 1406, 1352, 1272, 1195, 1170, 1057, 998, 888, 782 cm ^-1 . ¹ H NMR (600 MHz, CDCl ₃ ): d 11.84 (1H, s), 8.72 (1H, s), 8.32 (1H, d, J = 8.4 Hz), 8.02 (1H, s), 7.68 (2H, t , J = 7.8 Hz), 7.56 (1H, d, J = 7.8 Hz), 7.51 (1H, t, J = 8.4 Hz), 7.45-7.38 (4H, m), 7.34 (1H, d, J = 9.0 Hz ), 7.07 (1H, d, J = 8.4 Hz), 7.91 (1H, t, J = 7.8 Hz). ¹³ C NMR (150 MHz, CDCl ₃ ): d 199.1, 176.5, 163.2, 155.8, 155.2, 136.6, 136.4, 135.3, 134.3, 133.9, 133.2, 132.9, 131.7, 130.0, 139.9, 129.8, 128.7, 126.9, 126.7, 124.7, 121.5, 121.4, 119.1, 118.9, 118.5, 118.3. HRMS m / z (M ⁺ ): calcd for C ₂₆ H ₁₅ ClO ₄ : 426. 0659; found: 426. 0656.

2-17. 2- (2- Hydroxybenzoyl ) -4- (naphthalen-1-yl) -9H- Xanten -9-one [2- (2- Hydroxybenzoyl ) -4- (naphthalen-1-yl) -9H-xanthen-9-one; 5a]

Compound 5a was obtained as a pale yellow solid according to the above synthesis method; Yield: 68% (150 mg); mp; 215-217 ° C. IR (ATR): 2923, 1737, 1643, 1470, 1266, 1187, 890, 786, 687, 593 cm ^-1 . ¹ H NMR (600 MHz, CDCl ₃ ): d 11.88 (1H, s), 8.79 (1H, d, J = 2.4 Hz), 8.33 (1H, d, J = 7.8 Hz), 8.14 (1H, d, J = 1.2 Hz), 8.0 (1H, d, J = 8.4 Hz), 7.97 (1H, d, J = 8.4 Hz), 7.74 (1H, d, J = 7.8 Hz), 7.62-7.51 (6H, m), 7.40 (1H, t, J = 7.8 Hz), 7.36 (1H, t, J = 7.8 Hz), 7.09 (1H, d, J = 9.0 Hz), 7.04 (1H, d, J = 8.4 Hz), 6.92 ( 1H, t, J = 7.2 Hz). ¹³ C NMR (150 MHz, CDCl ₃ ): d 199.3, 176.8, 163.3, 155.8, 155.7, 137.1, 136.7, 135.2, 133.6, 133.2, 133.1, 131.8, 131.3, 129.1, 128.5, 128.4, 128.1, 126.6, 126.5, 126.1, 125.4, 125.3, 124.6, 121.5, 121.4, 119.1, 119.0, 118.6, 118.3. HRMS m / z (M ⁺ ): calcd for C ₃₀ H ₁₈ O ₄ : 442. 1205; found: 442. 1204.

2-18. 2- (2- Hydroxybenzoyl ) -4- (naphthalen-2-yl) -9H- Xanten -9-one [2- (2- Hydroxybenzoyl ) -4- (naphthalen-2-yl) -9H-xanthen-9-one; 5b]

Compound 5b was obtained as a white solid according to the above synthesis method; Yield: 69% (152 mg); mp; 127-129 ° C. IR (ATR): 2926, 1951, 1664, 1514, 1468, 1304, 1217, 1154, 753, 639, 547 cm ^-1 . ¹ H NMR (600 MHz, CDCl ₃ ): d 11.89 (1H, s), 8.68 (1H, d, J = 1.8 Hz), 8.35 (1H, d, J = 7.2 Hz), 8.21 (1H, d, J = 1.8 Hz), 8.12 (1H, s), 7.98 (1H, d, J = 7.8 Hz), 7.93-7.91 (2H, m), 7.80 (1H, dd, J = 7.8, 1.2 Hz), 7.72-7.69 (2H, m), 7.57-7.52 (3H, m), 7.41 (2H, t, J = 9.0 Hz), 7.09 (1H, d, J = 9.0 Hz), 6.91 (1H, t, J = 7.8 Hz) . ¹³ C NMR (150 MHz, CDCl ₃ ): d 199.4, 176.7, 163.3, 155.8, 155.1, 136.7, 136.0, 135.3, 133.3, 133.2, 133.1, 133.0, 132.8, 132.5, 129.0, 128.3, 128.0, 127.9, 127.7, 127.2, 126.7, 126.6, 124.7, 121.6, 121.5, 119.1, 119.0, 118.6, 118.3. HRMS m / z (M ⁺ ): calcd for C ₃₀ H ₁₈ O ₄ : 442. 1205; found: 422. 1202.

2-19. 2- (2- Hydroxy -5- Methylbenzoyl ) -7- methyl -4- (naphthalen-1-yl) -9H- Xanten -9 ions [2- (2- Hydroxy -5-methylbenzoyl) -7-methyl-4- (naphthalen-1-yl) -9H-xanthen-9-one; 5c]

Compound 5c was obtained as a pale yellow solid according to the above synthesis method; Yield: 78% (183 mg); mp; 153-155 ° C. IR (ATR): 2925, 1928, 1650, 1459, 1293, 1170, 1012, 721, 653 cm ^-1 . ¹ H NMR (600 MHz, CDCl ₃ ): d 11.68 (1H, s), 8.77 (1H, d, J = 2.4 Hz), 8.12-8.10 (2H, m), 7.99 (1H, d, J = 8.4 Hz ), 7.96 (1H, d, J = 7.8 Hz), 7.62-7.55 (3H, m), 7.52 (2H, dd, J = 15.6, 7.8 Hz), 7.41-7.39 (2H, m), 7.33 (1H, t, J = 7.2 Hz), 6.99 (1H, d, J = 7.8 Hz), 6.96 (1H, d, J = 8.4 Hz), 2.43 (3H, s), 2.27 (3H, s). ¹³ C NMR (150 MHz, CDCl ₃ ): d 199.4, 176.9, 161.2, 155.7, 154.1, 137.7, 137.0, 136.5, 134.6, 133.6, 133.2, 133.1, 133.0, 131.9, 131.1, 129.1, 128.5, 128.3, 128.1, 128.0, 126.5, 126.1, 126.0, 125.5, 125.4, 121.5, 121.2, 118.7, 118.4, 118.1, 20.8, 20.6. HRMS m / z (M ⁺ ): calcd for C ₃₂ H ₂₂ O ₄ : 470. 1518; found: 470. 1520.

2-20. 2- (2- Hydroxy -5- Methoxybenzoyl ) -7- Methoxy -4- (naphthalen-1-yl) -9H- Xanten -9-one [2- (2- Hydroxy -5-methoxybenzoyl) -7-methoxy-4- (naphthalen-1-yl) -9H-xanthen-9-one; 5d]

Compound 5d was obtained as a pale yellow solid according to the above synthesis method; Yield: 81% (203 mg); mp; 70-72 ° C. IR (ATR): 2927, 1927, 1637, 1465, 1274, 1164, 1032, 710, 650 cm ^-1 . ¹ H NMR (600 MHz, CDCl ₃ ): d 11.45 (1H, s), 8.83 (1H, d, J = 1.8 Hz), 8.13 (1H, d, J = 2.4 Hz), 7.99 (1H, d, J = 8.4 Hz), 7.97 (1H, d, J = 8.4 Hz), 7.86 (1H, d, J = 3.6 Hz), 7.60 (1H, t, J = 7.8 Hz), 7.55-7.50 (3H, m), 7.38 (1H, t, J = 7.2 Hz), 7.19-7.15 (3H, m), 7.03 (1H, d, J = 8.4 Hz), 6.99 (1H, d, J = 1.8 Hz), 3.38 (3H, s ), 3.71 (3H, s). ¹³ C NMR (150 MHz, CDCl ₃ ): δ 198.9, 176.6, 157.6, 156.5, 155.7, 151.7, 150.7, 136.8, 133.6, 133.2, 132.9, 131.8, 131.3, 129.1, 128.5, 128.4, 128.0, 126.5, 126.1, 125.4, 125.3, 125.3, 124.7, 121.8, 120.9, 120.9, 119.8, 118.4, 115.5, 105.7, 56.0, 55.9. HRMS m / z (M ⁺ ): calcd for C ₃₂ H ₂₂ O ₄ : 502. 1416; found: 502. 1419.

2-21. 7- Chloro -2- (5- Chloro -2- Hydroxybenzoyl ) -4- (naphthalen-1-yl) -9H- Xanten -9-one [7- Chloro -2- (5-chloro-2-hydroxybenzoyl) -4- (naphthalen-1-yl) -9H-xanthen-9-one; 5e]

Compound 5e was obtained as a pale yellow solid according to the above synthesis method; Yield: 74% (188 mg); mp 213-215 ° C. IR (ATR): 2963, 2271, 1843, 1639, 1380, 1268, 1184, 1061, 942, 791, 586 cm ^-1 . ¹ H NMR (600 MHz, CDCl ₃ ): d 11.68 (1H, s), 8.73 (1H, d, J = 1.8 Hz), 8.28 (1H, d, 2.4 Hz), 8.11 (1H, d, J = 2.4 Hz), 8.00 (1H, d, J = 7.8 Hz), 7.96 (1H, d, J = 7.8 Hz), 7.66 (1H, d, J = 2.4 Hz), 7.61 (1H, d, J = 7.8 Hz) , 7.55-7.51 (4H, m), 7.47 (1H, doublet of doublets, J = 9.0, 2.4 Hz), 7.42 (1H, doublet, J = 8.4 Hz), 7.04 (2H, doubled, J = 13.8, 9.6 Hz). ¹³ C NMR (150 MHz, CDCl ₃ ): d 198.3, 175.6, 161.7, 155.8, 154.1, 137.2, 136.6, 135.4, 133.6, 132.9, 132.6, 132.0, 131.7, 131.6, 130.6, 129.3, 128.6, 128.2, 128.1, 126.7, 126.2, 126.0, 125.3, 125.2, 123.8, 122.3, 121.3, 120.3, 120.1, 119.5. HRMS m / z (M ⁺ ): calcd for C ₃₀ H ₁₆ Cl ₂ O ₄ : 510.0426; found: 510.0424.

2-22. 2- (2- Hydroxybenzoyl ) -4- (phenanthrene-9-yl) -9H- Xanten -9-one [2- (2- Hydroxybenzoyl ) -4- (phenanthren-9-yl) -9H-xanthen-9-one; 5f]

Compound 5f was obtained as a pale yellow solid according to the above synthesis method. Yield: 57% (140 mg); mp; 115-117 ° C. IR (ATR): 2922, 1614, 1388, 1304, 1029, 946, 856, 745, 568 cm ^-1 . ¹ H NMR (600 MHz, CDCl ₃ ): d 11.89 (1H, s), 8.82 (2H, doublet, J = 7.2 Hz), 8.78 (1H, d, J = 8.4 Hz), 8.34 (1H, dd, J = 7.8, 1.2 Hz), 8.22 (1H, d, J = 2.4 Hz), 7.93 (1H, d, J = 7.8 Hz), 7.83 (1H, s), 7.77-7.72 (2H, m), 7.70-7.64 (2H, m), 7.58-7.51 (3H, m), 7.49 (1H, t, J = 8.4 Hz), 7.35 (1H, t, J = 7.8 Hz), 7.09 (1H, d, J = 8.4 Hz) , 6.98 (1H, d, J = 7.8 Hz), 6.93 (1H, t, J = 8.4 Hz). ¹³ C NMR (150 MHz, CDCl ₃ ): d 199.3, 176.7, 163.3, 156.0, 155.8, 137.0, 136.7, 135.2, 133.3, 133.2, 132.1, 131.5, 131.3, 130.7, 130.6, 130.4, 129.1, 128.9, 128.5, 127.4, 127.1, 126.8, 126.9, 126.6, 126.3, 124.7, 123.0, 122.7, 121.5, 121.4, 119.1, 118.9, 118.6, 118.3. HRMS m / z (M ⁺ ): calcd for C ₃₄ H ₂₀ O ₄ : 492. 1362; found: 492. 1359.

2-23. 2- (2- Hydroxybenzoyl ) -4- (thiophen-2-yl) -9H- Xanten -9-one [2- (2- Hydroxybenzoyl )-4-( thiophen -2-yl) -9H-xanthen-9-one; 5 g]

Compound 5g was obtained as a white solid according to the above synthesis method; Yield: 48% (95 mg); mp; 174-176 ° C. IR (ATR): 2997, 1840, 1700, 1639, 1372, 1253, 1178, 1057, 963, 899, 700, 662, 581 cm ^-1 . ¹ H NMR (600 MHz, CDCl ₃ ): d 11.85 (1H, s), 8.58 (1H, d, J = 1.8 Hz), 8.36 (2H, dd, J = 9.0, 1.8 Hz), 7.8 (1H, t , J = 7.8 Hz), 7.73 (1H, d, J = 3.6 Hz), 7.66-7.64 (2H, m), 7.54 (2H, t, J = 10.8 Hz), 7.45 (1H, t, J = 7.8 Hz ), 7.24-7.21 (1H, m), 7.10 (1H, d, J = 9.0 Hz), 6.91 (1H, t, J = 7.8 Hz). ¹³ C NMR (150 MHz, CDCl ₃ ): d 199.3, 176.5, 163.3, 155.9, 153.8, 136.8, 136.0, 135.5, 133.7, 133.3, 133.2, 127.7, 127.6, 127.5, 127.3, 126.9, 125.4, 125.0, 121.8, 121.5, 119.1, 118.9, 118.7, 118.3. HRMS m / z (M ⁺ ): calcd for C ₂₄ H ₁₄ O ₄ S: 398. 0613; found: 398. 0610.

2-24. 9- (1- Hydroxy -2- Naphthoyl ) -11- (p- Tolyl ) -7H- Benzo [c] xanthene -7-one [9- (1- Hydroxy -2- naphthoyl ) -11- (p-tolyl) -7H-benzo [c] xanthen-7-one; 6a]

Compound 6a was obtained as a yellow solid according to the above synthesis method; Yield: 56% (141 mg); mp; 250-252 ° C. IR (ATR): 2986, 1867, 1648, 1495, 1372, 1247, 979, 860, 750, 655, 566 cm ^-1 . ¹ H NMR (600 MHz, CDCl ₃ ): d 13.88 (1H, s), 8.77 (1H, d, J = 1.8 Hz), 8.55 (1H, d, J = 9.0 Hz), 8.37 (1H, d, J = 8.4 Hz), 8.30 (1H, d, J = 8.4 Hz), 8.21-8.22 (1H, m), 7.96 (1H, d, J = 7.8 Hz), 7.81-7.795 (2H, m), 7.74 (3H , t, J = 7.2 Hz), 7.69-7.64 (3H, m), 7.58 (1H, t, J = 7.2 Hz), 7.46 (2H, d, J = 7.8 Hz), 7.29 (1H, d, J = 9.6 Hz), 2.5 (3H, s). ¹³ C NMR (150 MHz, CDCl ₃ ): δ 199.4, 176.5, 164.9, 154.4, 153.8, 138.7, 137.5, 136.8, 135.3, 134.1, 132.7, 132.5, 130.6, 129.8, 129.7, 129.5, 128.2, 127.5, 127.3, 127.2, 126.9, 126.1, 125.3, 124.8, 124.6, 124.2, 123.3, 122.3, 121.3, 118.5, 117.43, 112.5, 21.4. HRMS m / z (M ⁺ ): calcd for C ₃₅ H ₂₂ O ₄ : 506. 1518; found: 506. 1520.

2-25. 11- (2- Bromophenyl ) -9- (1- Hydroxy -2- Naphthoyl ) -7H- Benzo [c] xanthene -7-one [11- (2- Bromophenyl ) -9- (1-hydroxy-2-naphthoyl) -7H-benzo [c] xanthen-7-one; 6b]

Compound 6b was obtained as a yellow solid according to the above synthesis method; Yield: 67% (224 mg); mp; 203-205 ° C. IR (ATR): 2986, 1867, 1648, 1495, 1372, 1247, 979, 860, 750, 655, 566 cm ^-1 . ¹ H NMR (600 MHz, CDCl ₃ ): d 13.83 (1H, s), 8.84 (1H, d, J = 1.8 Hz), 8.52 (1H, d, J = 8.4 Hz), 8.25 (1H, d, J = 8.4 Hz), 8.11 (1H, d, J = 1.8 Hz), 7.96 (1H, d, J = 8.4 Hz), 7.89 (2H, dd, J = 13.2, 7.8 Hz), 7.76 (2H, t, J = 8.4 Hz), 7.69-7.64 (3H, m), 7.57-7.51 (3H, m), 7.46-7.44 (1H, m), 7.27 (2H, d, J = 4.5 Hz. ¹³ C NMR (150 MHz, CDCl ₃ ): d 199.0, 176.3, 164.2, 154.4, 153.5, 137.4, 136.7, 136.5, 135.7, 133.8, 133.0, 131.9, 131.8, 130.6, 130.4, 129.8, 128.3, 128.0, 127.6, 127.5, 127.3, 126.9, 126.1 , 125.3, 124.8, 124.5, 124.1, 124.0, 122.8, 122.0, 121.2, 118.5, 117.5, 112.4.HRMS m / z (M ⁺ ): calcd for C ₃₄ H ₁₉ BrO ₄ : 570. 0467; found: 570. 0464 .

2-26. 9- (1- Hydroxy -2- Naphthoyl ) -11- (naphthalen-1-yl) -7H- Benzo [c] xanthene -7-one [9- (1- Hydroxy -2-naphthoyl) -11- (naphthalen-1-yl) -7H-benzo [c] xanthen-7-one; 6c]

Compound 6c was obtained as a yellow solid according to the above synthesis method. Yield: 61% (186 mg); mp; 219-221 ° C. IR (ATR): 3043, 1938, 1635, 1381, 1313, 1248, 1142, 1084, 993, 964, 774, 651, 560 cm ^-1 . ¹ H NMR (600 MHz, CDCl ₃ ): d 13.87 (1H, s), 8.89 (1H, d, J = 2.4 Hz), 8.53 (1H, d, J = 7.8 Hz), 8.28 (1H, d, J = 2.4 Hz), 8.25 (1H, d, J = 4.2 Hz), 8.09 (1H, t, J = 8.4 Hz), 8.04 (1H, d, J = 8.4 Hz), 7.82 (1H, d, J = 8.4 Hz), 7.77 (1H, d, J = 7.8 Hz), 7.73-7.64 (6H, m), 7.57-7.52 (3H, m), 7.38 (1H, t, J = 7.8 Hz), 7.29 (1H, d , J = 9.0 Hz), 7.22-7.19 (2H, m). ¹³ C NMR (150 MHz, CDCl ₃ ): d 199.2, 176.5, 164.2, 154.9, 153.5, 137.4, 136.6, 136.4, 134.1, 133.6, 133.2, 131.8, 131.5, 130.6, 129.7, 129.3, 128.5, 128.4, 128.0, 127.9, 127.5, 127.0, 126.9, 126.7, 126.2, 126.1, 125.8, 125.4, 125.3, 124.7, 124.6, 123.9, 122.7, 122.0, 121.1, 118.5, 117.4, 112.5. HRMS m / z (M ⁺ ): calcd for C ₃₈ H ₂₂ O ₄ : 542. 1518; found: 542. 1517.

2-27. 9- (1- Hydroxy -2- Naphthoyl ) -11- (naphthalen-2-yl) -7H- Benzo [c] xanthene -7-one [9- (1- Hydroxy -2-naphthoyl) -11- (naphthalen-2-yl) -7H-benzo [c] xanthen-7-one; 6d]

Compound 6d was obtained as a yellow solid according to the above synthesis method; Yield: 53% (143 mg); mp; 189-191 ° C. IR (ATR): 2981, 1906, 1805, 1632, 1379, 1261, 1181, 1090, 1043, 990, 796, 722, 575 cm ^-1 . ¹ H NMR (600 MHz, CDCl ₃ ): d 13.87 (1H, s), 8.80 (1H, s), 8.54 (1H, d, J = 8.4 Hz), 8.33 (1H, s), 8.30-8.28 (3H , m), 8.10 (1H, d, J = 8.4 Hz), 8.01-7.97 (3H, m), 7.92 (1H, d, J = 8.4 Hz), 7.78 (2H, d, J = 9.0 Hz), 7.69 -7.65 (3H, m), 7.62-7.60 (2H, m), 7.59-7.52 (2H, m), 7.28 (1H, d, J = 9.0 Hz). ¹³ C NMR (150 MHz, CDCl ₃ ): d 199.3, 176.5, 164.2, 154.5, 153.7, 137.5, 136.8, 135.6, 134.2, 133.5, 133.2, 132.9, 132.7, 130.6, 129.9, 129.2, 128.3, 128.2, 128.1, 127.9, 127.6, 127.5, 127.4, 127.3, 126.9, 126.8, 126.1, 125.3, 124.9, 124.6, 124.1, 123.2, 122.3, 121.3, 118.5, 117.5, 112.5, 105.7. HRMS m / z (M ⁺ ): calcd for C ₃₈ H ₂₂ O ₄ : 542. 1518; found: 542. 1519.

2-28. 9- (1- Hydroxy -2- Naphthoyl ) -11- (phenanthrene-9-yl) -7H- Benzo [c] xanthene -7-one [9- (1- Hydroxy -2-naphthoyl) -11- (phenanthren-9-yl) -7H-benzo [c] xanthen-7-one; 6e]

Compound 6e was obtained as a yellow solid according to the above synthesis method; Yield: 48% (156 mg); mp; 219-221 ° C. IR (ATR): 2926, 1844, 1752, 1626, 1383, 1237, 1131, 1036, 952, 867, 744, 567 cm ⁻¹ . ¹ H NMR (600 MHz, CDCl ₃ ): d 13.88 (1H, s), 8.92-8.89 (2H, m), 8.86 (1H, d, J = 8.4 Hz), 8.54 (1H, d, J = 8.4 Hz ), 8.37 (1H, d, J = 1.8 Hz), 8.27 (1H, d, J = 9.0 Hz), 7.97 (2H, d, J = 7.2 Hz), 7.81-7.77 (3H, m), 7.76-7.65 (6H, m), 7.56 (1H, t, J = 7.8 Hz), 7.52-7.50 (1H, m), 7.45 (1H, t, J = 7.8 Hz), 7.30 (1H, d, J = 8.4 Hz) , 7.12 (2H, doublet, J = 3.6 Hz). ¹³ C NMR (150 MHz, CDCl ₃ ): d 199.2, 176.5, 164.3, 155.2, 153.5, 137.5, 136.6, 136.3, 134.3, 132.3, 131.7, 131.4, 130.7, 130.6, 130.5, 129.7, 129.5, 129.0, 128.2, 127.8, 127.6, 127.5, 127.2, 127.0, 126.9, 126.8, 126.7, 126.6, 126.1, 125.3, 124.8, 124.6, 123.9, 123.1, 122.8, 122.6, 122.0, 121.1, 118.5, 177.4, 112.5. HRMS m / z (M ⁺ ): calcd for C ₄₂ H ₂₄ O ₄ : 592. 1675; found: 592. 1677.

2-29. 2- (2- Hydroxybenzoyl ) -4- (2- Methylprop -1-en-1-yl) -9H- Xanten -9-one [2- (2- Hydroxybenzoyl ) -4- (2-methylprop-1-en-1-yl) -9H-xanthen-9-one; 7a]

Compound 7a was obtained as a yellow solid according to the above synthesis method; Yield: 53% (98 mg); mp; 150-152 ° C. IR (ATR): 2975, 1746, 1653, 1570, 1437, 1308, 1258, 1178, 1152, 1071, 923, 740, 637 cm ^-1 . ¹ H NMR (600 MHz, CDCl ₃ ): d 11.89 (1H, s), 8.52 (1H, d, J = 1.2 Hz), 8.32 (1H, d, J = 8.4 Hz), 7.94 (1H, s), 7.75 (1H, t, J = 7.8 Hz), 7.64 (1H, d, J = 7.8 Hz), 7.57 (1H, d, J = 7.8 Hz), 7.52 (1H, t, J = 7.2 Hz), 7.41 ( 1H, t, J = 7.8 Hz), 7.08 (1H, d, J = 7.8 Hz), 6.89 (1H, t, J = 6.6 Hz), 6.57 (1H, s), 2.05 (3H, s), 1.88 ( 3H, s). ¹³ C NMR (150 MHz, CDCl ₃ ): d 199.7, 176.9, 163.2, 155.9, 155.7, 139.9, 136.5, 135.3, 135.2, 133.3, 132.6, 129.2, 126.7, 126.5, 124.6, 121.6, 121.1, 119.0, 118.9, 118.5, 118.3, 117.7, 26.8, 19.9. HRMS m / z (M ⁺ ): calcd for C ₂₄ H ₁₈ O ₄ : 370. 1205; found: 370. 1206.

2-30. 9- (1- Hydroxy -2- Naphthoyl ) -11- (2- Methylprop -1-en-1-yl) -7H- Benzo [c] xanthene -7-one [9- (1-Hydroxy-2-naphthoyl) -11- (2-methylprop-1-en-1-yl) -7H-benzo [c] xanthen-7-one; 7b]

Compound 7b was obtained as a yellow solid according to the above synthesis method; Yield: 56% (131 mg); mp; 223-225 ° C. IR (ATR): 2952, 1748, 1537, 1412, 1275, 1166, 1135, 1090, 1054, 939, 782, 678 cm ^-1 . ¹ H NMR (600 MHz, CDCl ₃ ): d 13.85 (1H, s), 8.62 (1H, d, J = 1.8 Hz), 8.57 (1H, d, J = 6.6 Hz), 8.52 (1H, d, J = 8.4 Hz), 8.25 (1H, d, J = 7.8 Hz), 8.01 (1H, d, J = 1.2 Hz), 7.97 (1H, d, J = 6.6 Hz), 7.76 (2H, d, J = 4.2 Hz), 7.74-7.70 (2H, m), 7.65-7.61 (2H, m), 7.54 (1H, t, J = 4.2 Hz), 7.25-7.24 (1H, m), 6.75 (1H, s), 2.15 (3H, s), 1.93 (3H, s). ¹³ C NMR (150 MHz, CDCl ₃ ): d 199.5, 176.5, 164.1, 154.9, 153.4, 140.2, 137.4, 136.8, 134.9, 133.5, 130.5, 129.8, 127.5, 128.2, 127.5, 127.2, 127.0, 126.2, 126.0, 125.3, 124.6, 124.5, 124.2, 122.8, 121.8, 121.4, 118.3, 117.6, 117.5, 112.5, 26.8, 20.0. HRMS m / z (M ⁺ ): calcd for C ₃₂ H ₂₂ O ₄ : 470. 1518; found: 470. 1515.

2-31. 4-( Cyclohex -2-en-1-yl) -2- (2- Hydroxybenzoyl ) -9H- Xanten -9-one [4- ( Cyclohex -2-en-1- yl ) -2- (2-hydroxybenzoyl) -9H-xanthen-9-one; 7c]

Compound 7c was obtained as a white solid according to the above synthesis method. Yield: 46% (91 mg); mp; 194-196 ° C. IR (ATR): 2926, 1554, 1389, 1304, 1234, 1123, 1037, 919, 742, 631, 574 cm ^-1 . ¹ H NMR (600 MHz, CDCl ₃ ): d 11.89 (1H, s), 8.53 (1H, d, J = 8.5 Hz), 8.33 (1H, d, J = 8.4 Hz), 7.93 (1H, d, J = 2.4 Hz), 7.75 (1H, t, J = 7.8 Hz), 7.63 (1H, d, J = 7.8 Hz), 7.53 (2H, t, J = 8.4 Hz), 7.41 (1H, t, J = 7.8 Hz), 7.08 (1H, d, J = 7.8 Hz), 6.90 (1H, t, J = 3.9 Hz), 6.03-6.19 (1H, m), 2.54-2.53 (2H, m), 2.29-2.28 (2H m), 1.87-1.83 (2H, m), 1.79-1.75 (2H, m). ¹³ C NMR (150 MHz, CDCl ₃ ): d 199.7, 176.9, 163.2, 156.0, 155.4, 136.5, 135.4, 135.2, 134.5, 134.4, 133.3, 133.0, 129.9, 127.1, 126.8, 124.6, 121.5, 121.2, 119.1, 118.5, 118.3, 29.1, 25.8, 22.9, 22.0. HRMS m / z (M ⁺ ): calcd for C ₂₆ H ₂₀ O ₄ : 396. 1362; found: 396. 1360.

2-32. One-( Benzylsulfonyl ) -4-methylbenzene [1- ( Benzylsulfonyl )-4- methylbenzene; 8 ]

Compound 8 was obtained in semi-liquid form according to the above synthesis method; Yield: 68% (84 mg); IR (ATR) 1235, 1180, 1031, 814 cm ^-1 . ¹ H NMR (600 MHz, CDCl ₃ ): d 7.62 (2H, d, J = 7.2 Hz), 7.33-7.28 (5H, m), 1.87 (2H, t, J = 7.8 Hz), 5.01 (1H, d , J = 11.4 Hz), 4.54 (1H, d, J = 10.8 Hz), 2.4 (3H, s). ¹³ C NMR (150 MHz, CDCl ₃ ): δ 142.8, 141.5, 135.5, 129.7, 129.7, 128.5, 128.3, 125.3, 65.5, 21.4. HRMS m / z (M ⁺ ): calcd for C ₁₄ H ₁₄ O ₂ S: 246.0707; found: 246.0711.

Having described the specific part of the present invention in detail, it is obvious to those skilled in the art that such a specific description is only a preferred embodiment, thereby not limiting the scope of the present invention. Do. That is, the substantial scope of the present invention is defined by the appended claims and their equivalents.

Claims (12)

Xanthone derivative represented by Formula 1, or a pharmaceutically acceptable salt thereof:
[Formula 1]

In Chemical Formula 1,
X is selected from the group consisting of substituted or unsubstituted aryl, heteroaryl, alkenyl and cycloalkenyl.
R ¹ and R ² may be different or the same each and are selected from the group consisting of hydrogen, (C 1 -C 4) alkyl, (C 1 -C 3) alkoxy, and halogen, or R ¹ and R ² are linked to each other to benzene Form a ring,
The substituted aryl is one to three hydrogen of the aromatic ring is substituted with any one or more substituents selected from the group consisting of (C1-C4) alkyl, (C1-C3) alkoxy, and halogen. The method of claim 1, wherein in Chemical Formula 1,
X is phenyl unsubstituted or substituted with any one or more substituents selected from the group consisting of methyl, methoxy, bromo, and chloro; Naphthalenyl; Phenanthracenyl; Thiophenyl; Butylenyl; And cyclohexenyl is any one selected from the group consisting of,
R ¹ and R ² may each be different or the same and are selected from the group consisting of hydrogen, methyl, isopropyl, methoxy, bromo, chloro, and fluoro, or R ¹ and R ² are linked to each other to benzene Xanthone derivative, or a pharmaceutically acceptable salt thereof, characterized by forming a ring. The method of claim 1, wherein the xanthone derivative is 2- (2-hydroxybenzoyl) -4-phenyl-9H-xanthene-9-one [2- (2-Hydroxybenzoyl) -4-phenyl-9H-xanthen-9- one], 2- (2-hydroxy-5-methylbenzoyl) -7-methyl-4-phenyl-9H-xanthene-9-one [2- (2-Hydroxy-5-methylbenzoyl) -7-methyl-4 -phenyl-9H-xanthen-9-one], 2- (2-hydroxy-5-isopropylbenzoyl) -7-isopropyl-4-phenyl-9H-xanthene-9-one [2- (2-Hydroxy -5-isopropylbenzoyl) -7-isopropyl-4-phenyl-9H-xanthen-9-one, 2- (2-hydroxy-5-methoxybenzoyl) -7-methoxy-4-phenyl-9H-xanthene- 9-one [2- (2-Hydroxy-5-methoxybenzoyl) -7-methoxy-4-phenyl-9H-xanthen-9-one], 7-bromo-2- (5-bromo-2-hydroxy Benzoyl) -4-phenyl-9H-xanthene-9-one [7-Bromo-2- (5-bromo-2-hydroxybenzoyl) -4-phenyl-9H-xanthen-9-one], 7-chloro-2- (5-chloro-2-hydroxybenzoyl) -4-phenyl-9H-xanthene-9-one [7-Chloro-2- (5-chloro-2-hydroxybenzoyl) -4-phenyl-9H-xanthen-9- one], 7-fluoro-2- (5-fluoro-2-hydroxybenzoyl) -4-phenyl-9H-xanthene-9-one [7-Fluoro-2- (5-fluoro-2-hydroxybenzoyl) -4-phenyl-9H-xanthen-9-one], 2-chloro-7- (5-chloro-2-hydroxy-4-methylbenzoyl) -3-methyl-5 -Phenyl-9H-xanthene-9-one [2-Chloro-7- (5-chloro-2-hydroxy-4-methylbenzoyl) -3-methyl-5-phenyl-9H-xanthen-9-one], 2- (5-Fluoro-2-hydroxybenzoyl) -7-methoxy-4-phenyl-9H-xanthene-9-one [2- (5-Fluoro-2-hydroxybenzoyl) -7-methoxy-4-phenyl- 9H-xanthen-9-one], 7-fluoro-2- (2-hydroxy-5-methoxybenzoyl) -4-phenyl-9H-xanthene-9-one [7-Fluoro-2- (2- hydroxy-5-methoxybenzoyl) -4-phenyl-9H-xanthen-9-one], 2- (2-hydroxybenzoyl) -4- (p-tolyl) -9H-xanthene-9-one [2- (2 -Hydroxybenzoyl) -4- (p-tolyl) -9H-xanthen-9-one], 4- (2,5-dimethylphenyl) -2- (2-hydroxybenzoyl) -9H-xanthene-9-one [ 4- (2,5-Dimethylphenyl) -2- (2-hydroxybenzoyl) -9H-xanthen-9-one], 2- (2-hydroxybenzoyl) -4- (3-methoxyphenyl) -9H-xanthene -9-one [2- (2-Hydroxybenzoyl) -4- (3-methoxyphenyl) -9H-xanthen-9-one], 4- (3,5-dimethoxyphenyl) -2- (2-hydroxybenzoyl ) -9H-Xanthene-9-one [4- (3,5-Dim ethoxyphenyl) -2- (2-hydroxybenzoyl) -9H-xanthen-9-one], 4- (2-bromophenyl) -2- (2-hydroxybenzoyl) -9H-xanthene-9-one [4- (2-Bromophenyl) -2- (2-hydroxybenzoyl) -9H-xanthen-9-one], 4- (2-chlorophenyl) -2- (2-hydroxybenzoyl) -9H-xanthene-9-one [ 4- (2-Chlorophenyl) -2- (2-hydroxybenzoyl) -9H-xanthen-9-one], 2- (2-hydroxybenzoyl) -4- (naphthalen-1-yl) -9H-xanthene-9 -One [2- (2-Hydroxybenzoyl) -4- (naphthalen-1-yl) -9H-xanthen-9-one], 2- (2-hydroxybenzoyl) -4- (naphthalen-2-yl)- 9H-Xanthene-9-one [2- (2-Hydroxybenzoyl) -4- (naphthalen-2-yl) -9H-xanthen-9-one], 2- (2-hydroxy-5-methylbenzoyl) -7 -Methyl-4- (naphthalen-1-yl) -9H-xanthen-9one [2- (2-Hydroxy-5-methylbenzoyl) -7-methyl-4- (naphthalen-1-yl) -9H-xanthen- 9-one], 2- (2-hydroxy-5-methoxybenzoyl) -7-methoxy-4- (naphthalen-1-yl) -9H-xanthene-9-one [2- (2-Hydroxy- 5-methoxybenzoyl) -7-methoxy-4- (naphthalen-1-yl) -9H-xanthen-9-one], 7-chloro-2- (5-chloro-2-hydroxybenzoyl) -4- (naphthalene -1-yl) -9H-xanthene-9- [7-Chloro-2- (5-chloro-2-hydroxybenzoyl) -4- (naphthalen-1-yl) -9H-xanthen-9-one], 2- (2-hydroxybenzoyl) -4- (phenan Tren-9-yl) -9H-xanthene-9-one [2- (2-Hydroxybenzoyl) -4- (phenanthren-9-yl) -9H-xanthen-9-one], 2- (2-hydroxybenzoyl ) -4- (thiophen-2-yl) -9H-xanthene-9-one [2- (2-Hydroxybenzoyl) -4- (thiophen-2-yl) -9H-xanthen-9-one], 9- (1-hydroxy-2-naphthoyl) -11- (p-tolyl) -7H-benzo [c] xanthene-7-one [9- (1-Hydroxy-2-naphthoyl) -11- (p-tolyl ) -7H-benzo [c] xanthen-7-one], 11- (2-bromophenyl) -9- (1-hydroxy-2-naphthoyl) -7H-benzo [c] xanthene-7-one [11- (2-Bromophenyl) -9- (1-hydroxy-2-naphthoyl) -7H-benzo [c] xanthen-7-one], 9- (1-hydroxy-2-naphthoyl) -11- (Naphthalen-1-yl) -7H-benzo [c] xanthene-7-one [9- (1-Hydroxy-2-naphthoyl) -11- (naphthalen-1-yl) -7H-benzo [c] xanthen- 7-one], 9- (1-hydroxy-2-naphthoyl) -11- (naphthalen-2-yl) -7H-benzo [c] xanthene-7-one [9- (1-Hydroxy-2- naphthoyl) -11- (naphthalen-2-yl) -7H-benzo [c] xanthen-7-one], 9- (1-hydroxy-2-naphthoyl) -11- (pe Tren-9-yl) -7H-benzo [c] xanthene-7-one [9- (1-Hydroxy-2-naphthoyl) -11- (phenanthren-9-yl) -7H-benzo [c] xanthen-7 -one], 2- (2-hydroxybenzoyl) -4- (2-methylprop-1-en-1-yl) -9H-xanthene-9-one [2- (2-Hydroxybenzoyl) -4- (2-methylprop-1-en-1-yl) -9H-xanthen-9-one], 9- (1-hydroxy-2-naphthoyl) -11- (2-methylprop-1-ene- 1-yl) -7H-benzo [c] xanthene-7-one [9- (1-Hydroxy-2-naphthoyl) -11- (2-methylprop-1-en-1-yl) -7H-benzo [c ] xanthen-7-one], 4- (cyclohex-2-en-1-yl) -2- (2-hydroxybenzoyl) -9H-xanthene-9-one [4- (Cyclohex-2-en- 1-yl) -2- (2-hydroxybenzoyl) -9H-xanthen-9-one], and 1- (benzylsulfonyl) -4-methylbenzene [1- (Benzylsulfonyl) -4-methylbenzene] Xanthone derivative, or a pharmaceutically acceptable salt thereof, characterized in that it is selected. A composition for detecting trivalent iron ions (Fe ³⁺ ) comprising a xanthone derivative represented by Formula 1 or a pharmaceutically acceptable salt thereof as an active ingredient:
[Formula 1]

In Chemical Formula 1,
X is selected from the group consisting of substituted or unsubstituted aryl, heteroaryl, alkenyl and cycloalkenyl.
R ¹ and R ² may be different or the same each and are selected from the group consisting of hydrogen, (C 1 -C 4) alkyl, (C 1 -C 3) alkoxy, and halogen, or R ¹ and R ² are linked to each other to benzene Form a ring,
The substituted aryl is one to three hydrogen of the aromatic ring is substituted with any one or more substituents selected from the group consisting of (C1-C4) alkyl, (C1-C3) alkoxy, and halogen. Kit for detecting ^trivalent iron ions (Fe ^{3 +} ) comprising the composition according to claim 4 as an active ingredient. Xanthan derivative represented by the formula (1), or a composition for sun protection comprising a pharmaceutically acceptable salt thereof as an active ingredient:
[Formula 1]

In Chemical Formula 1,
X is selected from the group consisting of substituted or unsubstituted aryl, heteroaryl, alkenyl and cycloalkenyl.
R ¹ and R ² may be different or the same each and are selected from the group consisting of hydrogen, (C 1 -C 4) alkyl, (C 1 -C 3) alkoxy, and halogen, or R ¹ and R ² are linked to each other to benzene Form a ring,
The substituted aryl is one to three hydrogen of the aromatic ring is substituted with any one or more substituents selected from the group consisting of (C1-C4) alkyl, (C1-C3) alkoxy, and halogen. The composition of claim 6, wherein the composition for sunscreen is a cosmetic composition. An antioxidant health functional food composition comprising an xanthone derivative represented by Formula 1, or a pharmaceutically acceptable salt thereof as an active ingredient:
[Formula 1]

In Chemical Formula 1,
X is selected from the group consisting of substituted or unsubstituted aryl, heteroaryl, alkenyl and cycloalkenyl.
R ¹ and R ² may be different or the same each and are selected from the group consisting of hydrogen, (C 1 -C 4) alkyl, (C 1 -C 3) alkoxy, and halogen, or R ¹ and R ² are linked to each other to benzene Form a ring,
The substituted aryl is one to three hydrogen of the aromatic ring is substituted with any one or more substituents selected from the group consisting of (C1-C4) alkyl, (C1-C3) alkoxy, and halogen. An antioxidant cosmetic composition comprising an xanthone derivative represented by Formula 1 or a pharmaceutically acceptable salt thereof as an active ingredient:
[Formula 1]

In Chemical Formula 1,
X is selected from the group consisting of substituted or unsubstituted aryl, heteroaryl, alkenyl and cycloalkenyl.
R ¹ and R ² may be different or the same each and are selected from the group consisting of hydrogen, (C 1 -C 4) alkyl, (C 1 -C 3) alkoxy, and halogen, or R ¹ and R ² are linked to each other to benzene Form a ring,
The substituted aryl is one to three hydrogen of the aromatic ring is substituted with any one or more substituents selected from the group consisting of (C1-C4) alkyl, (C1-C3) alkoxy, and halogen. A method of preparing a xanthone derivative, comprising reacting an N-tosylhydrazone derivative and a 3-formylchromone derivative at 70 ° C to 120 ° C in the presence of a base TEA. The method of claim 10, wherein the N-tosylhydrazone derivative is represented by Formula 2 below.
[Formula 2]

In Formula 2, A is any one selected from the group consisting of substituted or unsubstituted aryl, heteroaryl, alkenyl and cycloalkenyl,
The substituted aryl is one to three hydrogen of the aromatic ring is substituted with any one or more substituents selected from the group consisting of (C1-C4) alkyl, (C1-C3) alkoxy, and halogen. The method according to claim 10, wherein the 3-formylchromone derivative is represented by the following Chemical Formula 3:
[Formula 3]

In Chemical Formula 3, B ¹ and B ² may be the same or different, respectively, and are substituted with a substituent selected from the group consisting of hydrogen, (C 1 -C 4) alkyl, (C 1 -C 3) alkoxy, and halogen, or B ¹ and B ² are connected to each other to form a benzene ring.

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