CN108285411A - - 3 substitutions of 3,5- dihydroxy -1- methoxyl groups-benzene ketone compounds and the preparation method and application thereof - Google Patents

- 3 substitutions of 3,5- dihydroxy -1- methoxyl groups-benzene ketone compounds and the preparation method and application thereof Download PDF

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CN108285411A
CN108285411A CN201810070700.6A CN201810070700A CN108285411A CN 108285411 A CN108285411 A CN 108285411A CN 201810070700 A CN201810070700 A CN 201810070700A CN 108285411 A CN108285411 A CN 108285411A
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dihydroxy
ketone compounds
substitutions
alternaria
methoxyl groups
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CN108285411B (en
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钟添华
曾贤明
张永红
马新华
骆祝华
产竹华
谷力
杨献文
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Third Institute of Oceanography SOA
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
    • C07C49/84—Ketones containing a keto group bound to a six-membered aromatic ring containing ether groups, groups, groups, or groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C225/00—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones
    • C07C225/02—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C225/14—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being unsaturated
    • C07C225/16—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being unsaturated and containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P13/00—Preparation of nitrogen-containing organic compounds
    • C12P13/001—Amines; Imines
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
    • C12P17/02—Oxygen as only ring hetero atoms
    • C12P17/06—Oxygen as only ring hetero atoms containing a six-membered hetero ring, e.g. fluorescein
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P7/00—Preparation of oxygen-containing organic compounds
    • C12P7/24—Preparation of oxygen-containing organic compounds containing a carbonyl group
    • C12P7/26—Ketones

Abstract

3,5 dihydroxy, 1 methoxyl group, 3 substituted benzene ketone compounds and the preparation method and application thereof, are related to compound.3,5 dihydroxy, 1 methoxyl group, the 3 substituted benzene ketone compounds derive from marine fungi.Prepare the fermentation medicinal extract of bacterial strain rod method (Alternaria sp.) 3A00467；The extraction of bacterial strain rod method (Alternaria sp.) 3A00467 secondary metabolites detaches.One kind novel 3 with anti-tumor activity, 5 dihydroxy, 1 methoxyl group, 3 substituted benzene ketone compounds, the experiment proved that, there is good inhibiting effect to U266 (myeloma cell), HepG2 (human liver cancer cell), A549 (human lung carcinoma cell), therefore can be used for preparing antitumor drug.

Description

- 3 substitutions of 3,5- dihydroxy -1- methoxyl groups-benzene ketone compounds and preparation method thereof with Using
Technical field
The present invention relates to compounds, more particularly, to 3,5- dihydroxy -1- methoxyl groups -3 with anti-tumor activity substitution - Benzene ketone compounds and the preparation method and application thereof.
Background technology
In recent years, China's cancer morbidity rises year after year, and speed is fast, and scale is big to allow owner to shake for it, cancer Fast development, produce a series of social concern (publishing house of [1] clinical tumor complex treatment new concept [M] Tsinghua University Co., Ltd, 2006).The antitumor drug clinically applied at present mainly has the alkylating agents such as nitrogen mustards and metal pool class complex Class drug (common recognition suggestion [J] evidence-based medicine EBMs that [2] Sun Yan classify about antitumor drug, 2004,4 (3):190-191).This The mechanism of action of class drug is to form electron deficient reactive intermediate and other in vivo to have the compound of active electrophilic group, with Group containing abundant electronics in large biological molecule (DNA, RNA or enzyme), electrophilic covalent bond make macromolecular inactivate, hinder it Normal physiological function.But such compound alkylating agents chemical combination object is generated to cell and its strong toxic side effect, to increasing Long faster normal cell also will produce inhibiting effect, and long-term use easily generates drug resistance.Therefore it increases to having The discovery of the compound of antitumor activity seems particularly urgent with invention.
Invention content
The purpose of the present invention is to provide the 3,5- dihydroxy-with good antitumor activity and very big potential using value - 3 substitutions of 1- methoxyl groups-benzene ketone compounds and the preparation method and application thereof.
- 3 substitutions of 3, the 5- dihydroxy -1- methoxyl groups-benzene ketone compounds derive from marine fungi, the compound or The general structure of its addition salts is as follows：
In formula, R1Indicate H, OH, CH3、OCH3、CH2CH3、NH2、NO2、CnH2n-1、CnH2n-1OH；
R2Indicate H, OH, CH3、OCH3、CH2CH3、NH2、NO2、CnH2n-1、CnH2n-1OH；
R3Indicate H, OH, CH3、OCH3、CH2CH3、NH2、NO2、CnH2n-1、CnH2n-1OH；
R4Indicate H, OH, CH3、OCH3、CH2CH3、NH2、NO2、CnH2n-1、CnH2n-1OH；
R5Indicate H, OH, CH3、OCH3、CH2CH3、NH2、NO2、CnH2n-1、CnH2n-1OH；
R6Indicate H, OH, CH3、OCH3、CH2CH3、NH2、NO2、CnH2n-1、CnH2n-1OH；
R7Indicate H, OH, CH3、OCH3、CH2CH3、NH2、NO2、CnH2n-1、CnH2n-1OH；
Each R groups of the compound or its addition salts make following collocation：
(1)R1For H ︰ R2Can be H, OH, CH2CH3, CH2CH2OH, CH3C=OOCH2CH2And branched-chain or straight-chain alkyl.
(2) it can be H, OH, CH that R1, which is OH ︰ R2,2CH3, CH2CH2OH, CH3C=OOCH2CH2And branch or straight chain alkane Base.
(3) it can be H, OH, CH that R1, which is CH3CH2 ︰ R2,2CH3, CH2CH2OH, CH3C=OOCH2CH2And branch or straight Alkyl group.
(4) R4, R5 are H ︰ H, OH, CH2CH3, CH2CH2OH, CH3C=OOCH2CH2And branched-chain or straight-chain alkyl.
The preparation method of -3 substitutions of the 3,5- dihydroxy -1- methoxyl groups-benzene ketone compounds or its addition salts is as follows：
1) the fermentation medicinal extract of bacterial strain rod method (Alternaria sp.) 3A00467 is prepared；
In step 1), the specific of medicinal extract of fermenting for preparing bacterial strain rod method (Alternaria sp.) 3A00467 Method can be：The seed liquor for taking pipette, extract bacterial strain rod method (Alternaria sp.) 3A00467 is inoculated into solid containing No. 7 The solid fermentation product to get bacterial strain rod method (Alternaria sp.) 3A00467 is cultivated in the container of body culture medium；It is described Composition containing No. 7 solid mediums can be：Rice 80g, maltose 2%, glucose 1%, monosodium glutamate 1%, KH2PO40.05%, MgSO4·7H2O0.03%, yeast extract 0.3%, corn steep liquor 0.1%, mannitol 2%, CaCO32%, Chen Haishui；The container Can be used 1000ml conical flasks, the condition of the culture can in the constant incubator at 28 DEG C stationary culture 30d；The bacterium Strain rod method (Alternaria sp.) 3A00467 derives from State Oceanic Administration Bureau The Third Oceanography Institute's Chinese Sea microbial bacteria Kind preservation administrative center, address：Xiamen City, Fujian Province Siming District University Road 178, contact method：Phone：86(0)-592- 2195177, fax：86 (0) -592-219517, E-mail address：mccc5177@163.com.
2) the extraction separation of bacterial strain rod method (Alternaria sp.) 3A00467 secondary metabolites.
In step 2), the specific method of the extraction separation can be：By bacterial strain rod method (Alternaria sp.) The solid fermentation product of 3A00467 is impregnated with methanol, is repeated after extracting 3~4 times, is merged extracting solution, be concentrated under reduced pressure into without first It after alcohol, is suspended with water, then is extracted 3~4 times with isometric ethyl acetate, combined ethyl acetate extract liquor is simultaneously concentrated under reduced pressure into It is dry, the acetic acid ethyl ester extract 18.6g of bacterial strain rod method (Alternaria sp.) 3A00467 is obtained, using thin-layer chromatography, instead The separation sides such as efficient liquid phase are prepared to ODS silica gel column chromatographies, sephadex column chromatography, normal phase silica gel chromatography column chromatography and half Method.
The present invention is -3 substitutions of the novel 3,5- dihydroxy -1- methoxyl groups of one kind with anti-tumor activity-benzophenone class chemical combination Object, the experiment proved that, it has well U266 (myeloma cell), HepG2 (human liver cancer cell), A549 (human lung carcinoma cell) Inhibiting effect, therefore can be used for preparing antitumor drug.
Description of the drawings
Fig. 1 is that the compound of the embodiment of the present invention isolates and purifies flow chart.
Specific implementation mode
- 3 substitutions of 3, the 5- dihydroxy -1- methoxyl groups-benzene ketone compounds derive from marine fungi, the compound or The general structure of its addition salts is as follows：
In formula, R1Indicate H, OH, CH3、OCH3、CH2CH3、NH2、NO2、CnH2n-1、CnH2n-1OH；
R2Indicate H, OH, CH3、OCH3、CH2CH3、NH2、NO2、CnH2n-1、CnH2n-1OH；
R3Indicate H, OH, CH3、OCH3、CH2CH3、NH2、NO2、CnH2n-1、CnH2n-1OH；
R4Indicate H, OH, CH3、OCH3、CH2CH3、NH2、NO2、CnH2n-1、CnH2n-1OH；
R5Indicate H, OH, CH3、OCH3、CH2CH3、NH2、NO2、CnH2n-1、CnH2n-1OH；
R6Indicate H, OH, CH3、OCH3、CH2CH3、NH2、NO2、CnH2n-1、CnH2n-1OH；
R7Indicate H, OH, CH3、OCH3、CH2CH3、NH2、NO2、CnH2n-1、CnH2n-1OH；
Each R groups of the compound or its addition salts make following collocation：
(1)R1For H ︰ R2Can be H, OH, CH2CH3, CH2CH2OH, CH3C=OOCH2CH2And branched-chain or straight-chain alkyl.
(2) it can be H, OH, CH that R1, which is OH ︰ R2,2CH3, CH2CH2OH, CH3C=OOCH2CH2And branch or straight chain alkane Base.
(3) it can be H, OH, CH that R1, which is CH3CH2 ︰ R2,2CH3, CH2CH2OH, CH3C=OOCH2CH2And branch or straight Alkyl group.
(4) R4, R5 are H ︰ H, OH, CH2CH3, CH2CH2OH, CH3C=OOCH2CH2And branched-chain or straight-chain alkyl.
The structure of -3 substitutions of the 3,5- dihydroxy -1- methoxyl groups-benzene ketone compounds or its addition salts is shown in Table 1.
Table 1
Compound R1 R2 R3 R4 R5 R6 R6
1 CH3 H H OH
2 CH2CH3 H H H
3 CH3 H H H
4 CH3 H H OOCCH3
5 CH2CO(CH2)2CH3 CH2CH3 H OH
6
7 H H CH3
8 H OH (CH2)2CH3
9 H H (CH=CH2)CH3
10 H NHCH3 CH2CH3
The preparation method of -3 substitutions of the 3,5- dihydroxy -1- methoxyl groups-benzene ketone compounds or its addition salts is as follows：
1) the fermentation medicinal extract of bacterial strain rod method (Alternaria sp.) 3A00467 is prepared：Take pipette, extract bacterial strain chain The seed liquor of lattice spore (Alternaria sp.) 3A00467 is inoculated into the container containing No. 7 solid mediums and cultivates to get bacterium The solid fermentation product of strain rod method (Alternaria sp.) 3A00467；The composition for containing No. 7 solid mediums can be： Rice 80g, maltose 2%, glucose 1%, monosodium glutamate 1%, KH2PO40.05%, MgSO4·7H2O 0.03%, yeast extract 0.3%, corn steep liquor 0.1%, mannitol 2%, CaCO32%, Chen Haishui；1000ml conical flasks, institute can be used in the container State culture condition can in the constant incubator at 28 DEG C stationary culture 30d.
2) the extraction separation of bacterial strain rod method (Alternaria sp.) 3A00467 secondary metabolites, by bacterial strain chain lattice The solid fermentation product of spore (Alternaria sp.) 3A00467 is impregnated with methanol, is repeated after extracting 3~4 times, is merged extraction Liquid is concentrated under reduced pressure into without after methanol, is suspended with water, then extracted 3~4 times with isometric ethyl acetate, combined ethyl acetate Extract liquor is simultaneously concentrated to dryness, and obtains the acetic acid ethyl ester extract of bacterial strain rod method (Alternaria sp.) 3A00467 18.6g, using thin-layer chromatography, reversed ODS silica gel column chromatographies, sephadex column chromatography, normal phase silica gel chromatography column chromatography and Half prepares the separation methods such as efficient liquid phase.
Antitumor cytolytic activity experiment is given below：
The human tumor cell line of logarithmic growth phase is configured to suitable concentration, about 3 × 10 with complete culture solution4-6×104 A/mL is inoculated on 96 well culture plates, and per 100 μ L of hole, each concentration sets 2 multiple holes, and blank control group sets 4 multiple holes, mistake Night culture keeps its adherent.
Appropriate amount of drug is weighed, the solution of a concentration of 40,20,10,5,2.5,1.25 μ g/mL is configured to complete culture solution, Original fluid in 96 orifice plates is drawn, the drug solution of above-mentioned various concentration is added, per 100 μ L of hole, is made under conventional culture conditions After 48h, 20 μ L MTT solution (being prepared with PBS, pH=7.4) are then added per hole, continues to train 4h, by centrifugation, discard Clearly, dimethyl sulfoxide (DMSO) (DMSO) 150 μ L then are added in every hole, 10min are shaken, with microplate reader (BIO-RAD products) in OD The light absorption value in each hole is measured at 490nm, each group is averaged, according to mean value calculation inhibiting rate, is counted with SPSS12.0 Credit is analysed, and calculates IC50Value, part of compounds antitumor activity are shown in Table 2.
2 (IC of table50μg/mL)
Compound U266 HepG2 A549
1 15.48 33.52 >100
2 >100 >100 >100
3 >100 >100 >100
4 70.4 80.6 78.5
5 21.98 25.77 >100
6 24.99 33.16 80.25
7 23.49 15.6 61.15
8 14.78 15.79 20.41
9 13.26 14.69 24.39
10 97 >100 >100
It can be seen that compound of the present invention have antitumor activity, especially compound 1,5,6,7,8,9 have compared with Strong antitumor activity.

Claims (10)

1.3,5- -3 substitutions of dihydroxy -1- methoxyl groups-benzene ketone compounds, it is characterised in that the compound or its addition salts General structure is as follows：
In formula, R1Indicate H, OH, CH3、OCH3、CH2CH3、NH2、NO2、CnH2n-1、CnH2n-1OH；
R2Indicate H, OH, CH3、OCH3、CH2CH3、NH2、NO2、CnH2n-1、CnH2n-1OH；
R3Indicate H, OH, CH3、OCH3、CH2CH3、NH2、NO2、CnH2n-1、CnH2n-1OH；
R4Indicate H, OH, CH3、OCH3、CH2CH3、NH2、NO2、CnH2n-1、CnH2n-1OH；
R5Indicate H, OH, CH3、OCH3、CH2CH3、NH2、NO2、CnH2n-1、CnH2n-1OH；
R6Indicate H, OH, CH3、OCH3、CH2CH3、NH2、NO2、CnH2n-1、CnH2n-1OH；
R7Indicate H, OH, CH3、OCH3、CH2CH3、NH2、NO2、CnH2n-1、CnH2n-1OH。
2.-3 substitutions of 3,5- dihydroxy-1- methoxyl groups as described in claim 1-benzene ketone compounds, it is characterised in that describedization Each R groups for closing object or its addition salts make following collocation：
(1)R1For H ︰ R2For H, OH, CH2CH3, CH2CH2OH, CH3C=OOCH2CH2And branched-chain or straight-chain alkyl；
(2) it is H, OH, CH that R1, which is OH ︰ R2,2CH3, CH2CH2OH, CH3C=OOCH2CH2And branched-chain or straight-chain alkyl；
(3) it is H, OH, CH that R1, which is CH3CH2 ︰ R2,2CH3, CH2CH2OH, CH3C=OOCH2CH2And branched-chain or straight-chain alkyl；
(4) R4, R5 are H ︰ H, OH, CH2CH3, CH2CH2OH, CH3C=OOCH2CH2And branched-chain or straight-chain alkyl.
3. the preparation method of-3 substitutions of 3,5- dihydroxy-1- methoxyl groups as described in claim 1-benzene ketone compounds, feature It is to include the following steps：
1) the fermentation medicinal extract of bacterial strain rod method (Alternaria sp.) 3A00467 is prepared；
2) the extraction separation of bacterial strain rod method (Alternaria sp.) 3A00467 secondary metabolites.
4. the preparation method of-3 substitutions of 3,5- dihydroxy-1- methoxyl groups as claimed in claim 3-benzene ketone compounds, feature It is in step 1), the specific method of the fermentation medicinal extract for preparing bacterial strain rod method (Alternaria sp.) 3A00467 For：The seed liquor for taking pipette, extract bacterial strain rod method (Alternaria sp.) 3A00467, is inoculated into containing No. 7 solid cultures The solid fermentation product to get bacterial strain rod method (Alternaria sp.) 3A00467 is cultivated in the container of base.
5. the preparation method of-3 substitutions of 3,5- dihydroxy-1- methoxyl groups as claimed in claim 4-benzene ketone compounds, feature It is that the group containing No. 7 solid mediums becomes：Rice 80g, maltose 2%, glucose 1%, monosodium glutamate 1%, KH2PO4 0.05%, MgSO4·7H2O 0.03%, yeast extract 0.3%, corn steep liquor 0.1%, mannitol 2%, CaCO32%, Chen Haishui.
6. the preparation method of-3 substitutions of 3,5- dihydroxy-1- methoxyl groups as claimed in claim 4-benzene ketone compounds, feature It is that the container uses 1000ml conical flasks.
7. the preparation method of-3 substitutions of 3,5- dihydroxy-1- methoxyl groups as claimed in claim 4-benzene ketone compounds, feature It is stationary culture 30d in constant incubator of the condition of the culture at 28 DEG C.
8. the preparation method of-3 substitutions of 3,5- dihydroxy-1- methoxyl groups as claimed in claim 4-benzene ketone compounds, feature It is that the bacterial strain rod method (Alternaria sp.) 3A00467 derives from State Oceanic Administration Bureau The Third Oceanography Institute's China sea Foreign Microbiological Culture Collection administrative center.
9. the preparation method of-3 substitutions of 3,5- dihydroxy-1- methoxyl groups as claimed in claim 3-benzene ketone compounds, feature It is in step 2), the specific method of the extraction separation is：By bacterial strain rod method (Alternaria sp.) 3A00467's Solid fermentation product is impregnated with methanol, after repeating extraction 3~4 times, is merged extracting solution, is concentrated under reduced pressure into without after methanol, with water It is suspended, then is extracted 3~4 times with isometric ethyl acetate, combined ethyl acetate extract liquor is simultaneously concentrated to dryness, and obtains bacterial strain The acetic acid ethyl ester extract 18.6g of rod method (Alternaria sp.) 3A00467, using thin-layer chromatography, reversed ODS silicagel columns Chromatography, sephadex column chromatography, normal phase silica gel chromatography column chromatography and half prepare the separation methods such as efficient liquid phase.
10.-3 substitutions of 3,5- dihydroxy-1- methoxyl groups as described in claim 1-benzene ketone compounds are preparing antitumor drug Middle application, the tumour include U266 (myeloma cell), HepG2 (human liver cancer cell), A549 (human lung carcinoma cell).
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