JPH0723390B2 - Sugar ester of 2-cyclopentenones and method for producing the same - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION <Field of Industrial Application> The present invention relates to a sugar ester of 2-cyclopentenones and a method for producing the same.

<Prior Art> Prostaglandins are compounds having specific biological activities such as an inhibitory effect on platelet aggregation and an antihypertensive effect, and are useful as therapeutic agents for peripheral cardiovascular disease in the medical field in recent years. It is a natural product. Among prostaglandins, prostaglandins A are known as those having a double bond in the cyclopentane ring, and, for example, prostaglandin A ₂ is expected as a drug having a hypotensive action [e.・ J Corey (EJCore
y) et al., Journal of the American Chemical Society (J.Amer.Chem.Soc.), 95 , 6831 (197).
See 3)].

Further, since prostaglandins A strongly suppress DNA synthesis, the possibility that prostaglandins A as antitumor agents has been reported [Biochemical and Biophysical Research Communication (Bioc
hem.Biophys.Res, Commun.), 87 , 795,1979; W. Turner et al., Prostaglandins and Related Rapids (Prostaglandi)
ns Relat, Lipids), 2, 365-8 (1982)].

European Published Patent No. 0106576 (Publication Date: April 25, 1984) describes 4,5-substituted 2 including prostaglandin A class.
-Cyclopentenones are known and described to be effective for malignant tumors.

Further, it is known that prostaglandins D and J different from prostaglandins A are useful as antitumor agents [JP-A-58-216155 and Proceedings of the National].・ Academy of Science is of the United States of America (Proc.Natl.Acad.Sci.USA), 8
1 , 1317-1321 (1984)].

Also, the following formula The prostaglandin analog represented by is isolated from the Okinawa coral [Okinawa Soft coral: clavularia viridis] and is known to have anti-inflammatory and anti-cancer effects as physiological actions [ Kikuchi et al., Tetrahedron Le
tt.), 23 , 5171 (1982); Kobayashi et al., Tetrahedron Lett., 23 , 5331 (1982); Fukushima, Masanori, Cancer and Chemotherapy, 10 , 1931 (1983)].

Furthermore, from the telesto riisei that have recently been collected on the ship's bottom collected on Oahu, The punaglandins represented by are isolated, and Masanori Fukushima et al. Have announced that these compounds have antitumor activity (Masanori Fukushima et al., The 43rd Annual Meeting of the Japanese Cancer Society 905 (198
See 4)).

However, these groups of antitumor prostaglandins are not limited to natural products and synthetic compounds, and their excellent cytotoxic activity (for example, Punagradin L-1210 cell IC ₅₀ = 0.1 to 0.0).
5 μg / ml), the antitumor activity in vivo was weak.

<Problems to be Solved by the Invention> An object of the present invention is to provide novel 2-cyclopentenones, that is, novel synthesized clavurones or punaglandins or prostaglandins A.

That is, the object of the present invention is to provide a known natural or synthetic compound.
It is said to provide novel 2-cyclopentenones that exhibit superior in vivo superior antitumor activity as compared with PGAs, PGDs, clavrons, and punaglandins.

Still another object of the present invention is to provide a method for producing the 2-cyclopentenones of the present invention.

<Means for Solving the Present Invention> The present invention has the following formula [I]: To provide 2-cyclopentenones.

In the above formula [I], R ¹ represents a saccharide residue. Among the saccharides, monosaccharides are preferable, and examples thereof include allose, altrose, glucose, mannose, idose, galactose, talose, ribose, arabinose, xylose,
Lyxose, erythrose, threose, psicose,
Examples include fructose, sorbose, tagatose, etc., which form sugar esters. The binding site as a sugar ester is condensed with a carboxylic acid at the site when the sugar has a primary alcohol in the sugar, and at the 1-position otherwise, to form a sugar ester.

In the above formula [I], R ² is a substituted or unsubstituted C 1
It represents an alkyl group having 10 to 10 and an alkenyl group having 2 to 10 carbon atoms. These may be linear or branched.

As the unsubstituted alkyl group, for example, methylethyl, n
-Propyl, iso-propyl, n-butyl, sec-butyl, ter
t-butyl, n-pentyl, n-hexyl, n-heptyl, n-
Examples include octyl, n-nonyl group and n-decyl group.

Examples of the unsubstituted alkenyl group include ethenyl, 1-
Propen-1-yl, 2-propen-1-yl, 1-buten-1-yl, 1,3-butadiene-1-yl, 2-butene-1
-Yl, 1-penten-1-yl, 2-penten-1-yl, 1-hexen-1-yl, 2-hexen-1-yl, 1,5
-Hexadiene-1-yl, 3-hexen-1-yl, 1-
Hepten-1-yl, 1-octen-1-yl, 1,7-octadien-1-yl, 1-nonen-1-yl group or 1-
A decen-1-yl group etc. can be mentioned. These alkyl group and alkenyl group may have a substituent. This substituent represents -OR ³ (here, R ³ is a hydrogen atom; an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or a phenyl group which may be substituted with a halogen atom). ), And a hydrogen atom or a phenyl group is particularly preferable as R ³ .

In addition, the following formula [II] which is a raw material of the above formula [I] The same applies to R ^{2 in} .

In the above formula [I] or [II], the skeleton contains an asymmetric carbon. That is, the carbon atom substituted by R ² and
-O when substituent -OR ³ on which R ² is secondary or tertiary
R ³ is a substituted carbon atom.

The compounds of the present invention can have the R or S configuration for each of these asymmetric carbon atoms and also include mixtures thereof in any proportion.

Examples of the sugar ester raw material compounds of the 2-cyclopentenones represented by the above formula [II] include the following compounds.

Thiazolidine-2-thionamide of 1.5- (4-carboxybutynylidene) -4-hydroxy-4-phenoxybutyl-2-cyclopentenone 2.5- (4-carboxyhexanilidene) -4-hydroxy-4-phenoxybutyl 2-Cyclopentenone Thiazolidine-2-Thionamide 3.5- (4-Carboxy-2-hexenylidene) -4-
Thiazolidine-2-thioneamide of hydroxy-4-phenoxybutyl-2-cyclopentenone 4. Thiazolidine-2-thioneamide of Δ7-prostaglandin A _{1 and} the like are mentioned, but not limited thereto. Further, the sugar ester of 2-cyclopentenones represented by the above formula [I] includes D of 1.5- (4-carboxybutynylidene) -4-hydroxy-4-phenoxybutyl-2-cyclopentenone.
-Xylose sugar ester 2.5- (4-Carboxyhexanilidene) -4-hydroxy-4-phenoxybutyl-2-cyclopentenone D-glucose sugar ester 3.5- (4-Carboxyhexanilidene) -4-hydroxy- D-xylose sugar ester of 4-phenoxybutyl-2-cyclopentenone 4.5- (4-carboxy-2-hexenylidene) -4-
Hydroxy-4-phenoxybutyl-2-cyclopentenone D-glucose sugar ester 5.5- (4-Carboxybutynylidene) -4-hydroxy-4-phenoxybutyl-2-cyclopentenone D
-Glucose sugar ester 6. A D-ribose sugar ester of Δ7-prostaglandin A ₁ can be mentioned.

According to the present invention, the sugar ester of 2-cyclopentenone of the above formula [I] of the present invention is represented by the following formula [II] It can be produced by reacting the compound represented by with a saccharide in the presence of a basic compound. This reaction can be basically carried out according to the method known in the literature, that is, the method described in Daniel Plusquellec et al., Tetrahedron Letters, 28 , 3809 (1987), There are no examples of 2-cyclopentenones which are relatively unstable to basic conditions as in the present invention.

Examples of the solvent used in the synthesis of the sugar ester include ethers such as ether and tetrahydrofuran;
Hydrocarbons such as petroleum ether, hexane, benzene and pentane, halogens such as methylene chloride and the like may be used, but pyridine which is a basic solvent may be used, and pyridine is preferably used.

Further, in the reaction, other base is added separately, and 4-dimethylaminopyridine and sodium hydride are used as the base. The amount used is, for example, 0.02 equivalent to 2 equivalents to the compound of the above formula [II]. , 0.01 equivalent to 1 equivalent, preferably 0.05 equivalent to 0.5 equivalent,
It is 0.05 equivalent to 0.5 equivalent. The reaction temperature is -20 ° C to 80 ° C, preferably 0 ° C to 40 ° C. The reaction time varies depending on the amount of base, the reaction temperature, and the type of sugar used, but is usually 30 minutes to 20 hours.

On the other hand, the sugar that is the partner of the reaction is basically the above formula [II].
The compound is reacted in an equivalent amount, but usually 0.5 to 10 equivalents are used.

After completion of the reaction, the product is treated by conventional means such as extraction, washing with water,
It can be purified and fractionated by drying, chromatography and the like. Thus, the sugar ester of 2-cyclopentenones represented by the above formula [I] of the present invention can be obtained by the above method.

The thiazoline-2-thio-amide compound represented by the above formula [II], which is an activated carboxylic acid compound used as a starting material for the above reaction, can be prepared by a method known per se, that is, by the inventors separately. It can be obtained by using the mixed acid anhydride method for the carboxylic acid body (compound A or B in FIG. 1 or FIG. 2 below) obtained by the proposed method. For example, the route is as shown in FIG. 1 or FIG.

Thus, the compound of the above formula [I] can be produced by obtaining the thiazoline-2-thio-amide compound (the above formula [II] compound) which is the compound of the present invention and then subjecting it to sugar esterification.

The 2-cyclopentenones of the present invention showed a growth-suppressing effect on L-1210 leukemia cells, and further, an excellent survival rate improvement was observed in the evaluation of in vivo activity of mice on p388 mouse leukemia cells. . While conventional prostaglandin-based carcinostatic compounds have shown strong cytostatic activity in vitro, in many cases, their life-prolonging effect could not be obtained in vivo. As one of the causes of this, the toxicity of the compound itself was considered. The sugar ester of 2-cyclopentenone in the present invention does not show side effects at the same dose (30 mg / kg) as compared with the conventional 2-cyclopentenone analog, and thus can be expected as a useful anticancer agent. It is a compound.

The present invention will be specifically described below with reference to examples.

Example 1 Synthesis of thiazolidine-2-thionamide of 5- (4-carboxybutynylidene) -4-hydroxy-4-phenoxybutyl-2-cyclopentenone A solution of 300 mg (0.87 mmol) of carboxylic acid in methylene chloride (5 m
111 μl (0.8 mmol) of triethylamine was added to
After cooling to 0 ° C, 100 μl of pivaloyl chloride (0.8 mmo
l) was added and stirred for 2 hours. Next, 86 mg (0.72 mmol) of 2-mercaptothiazoline and 8.5 mg (0.07 mmol) of DMAP were added, and the mixture was stirred at room temperature for 2 hours. The reaction was terminated with aqueous NaHCO _{3 and} extracted with methylene chloride. Organic layer is KHSO ₄ water, N
It was washed with aHCO ₃ water and NaCl water, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the obtained oily substance was subjected to silica gel column chromatography (hexane: ethyl acetate = 2: 3 → 1: 1) to obtain 300 mg (77%) of N-acylthiazolidine-2-thione. It was

NMR (δ ppm, CDCl ₃ ): 1.1-3.0 (m, 12H), 3.25 (m, 2H), 3.9 (d, 2H, J = 6Hz),
4.5 (m, 2H), 6.2-6.6 (m, 2H), 6.7-7.0 (m, 3H), 7.1
-7.4 (m, 3H). Example 2 D- of 5- (4-carboxybutynylidene) -4-hydroxy-4-phenoxybutyl-2-cyclopentenone
Synthesis of sugar ester of glucose (position 6) N-acyl thiazolidine-2-thione 150mg (0.29mmo
l) 1 ml pyridine solution was added with D-glucose 162 mg (0.90 mmo
l) in 4 ml pyridine solution, then NaH (60% in oi
l) 5 mg and DMAP 5 mg were added, and the mixture was stirred for 16 hours at room temperature. After the reaction, pyridine was distilled off under reduced pressure, n-butanol 4 ml, pH 7.0.
Extraction was performed by adding 4 ml of 1M phosphate buffer. The organic layer was washed with saturated saline acidified with acetic acid. The n-butanol in the organic layer was distilled off under reduced pressure, and then silica gel-Seβ-pack (CH
₂ Cl ₂ → CH ₂ Cl ₂ -acetone 2/1 → 1/1 → acetone)
95 mg (58%) of the sugar ester was obtained.

NMR (δ ppm, CDCl ₃ ): 1.1-2.9 (m, 12H), 3.0-5.3 (m, 13H), 6.1-6.7 ((m,
2H), 6.7-7.05 (m, 3H), 7.05-7.5 (m, 3H). IR (cm ^-1 , neat): 3400,2950,1740,1700,1660,1600,1590,1500,1420,1250,
1090, 1040. Example 3 D- of 5- (4-carboxybutynylidene) -4-hydroxy-4-phenoxybutyl-2-cyclopentenone
Synthesis of sugar ester of xylose (1st position) N-acyl thiazolidine-2-thione 290mg (0.65mmo
l) and D-xylose 300 mg (2 mmol) in 6 ml pyridine solution, then add NaH (60% in oil) 5 mg, DMAP 5 mg,
Stir for 6 hours at room temperature. After the reaction, pyridine was distilled off under reduced pressure, and 6 ml of n-butanol, 6 ml of pH 7, 0.1M phosphate buffer was added for extraction. The organic layer was washed with saturated saline acidified with acetic acid. The n-butanol in the organic layer was distilled off under reduced pressure, followed by silica gel column chromatography (CHCl ₃ : MeOH: A
cOH = 80: 5: 4 → 80: 10: 4) and refined with sugar ester 150mg
(48%) obtained.

NMR (δ ppm, CDCl ₃ ): 1.1-2.9 (m, 12H), 3.0-5.3 (m, 12H), 6.1-6.7 ((m,
2H), 6.7-7.05 (m, 3H), 7.05-7.5 (m, 3H). Example 4 Thiazolidine-2-thioneamide synthesis of 5- (4-Carboxyhexanilidene) -4-hydroxy-4-phenoxybutyl-2-cyclopentenone To 10 ml of 10 ml of a dry methylene chloride solution containing 650 mg (1.74 mmol) of carboxylic acid, 270 μl (1.92 mmol) of triethylamine was added, and the mixture was cooled to −20 ° C. under N ₂ and then pivaloyl chloride 23
8 μl (1.92 mmol) was added and stirred for 2 hours. Then 2
-Methylcaptothiazoline (214 mg, 1.8 mmol) and dimethylaminopyridine (22 mg, 0.18 mmol) were added, and the mixture was stirred at room temperature for 5 hours. About 10 ml of 0.5N HCl was added, and the mixture was extracted with methylene chloride. The organic layer was washed with aqueous NaHCO ₃ and saturated aqueous NaCl, and dried over anhydrous magnesium sulfate. After separation, the solvent was evaporated under reduced pressure, and the obtained oil was subjected to silica gel column chromatography (hexane: ethyl acetate = 1: 1 → 2: 3),
716 mg (87%) of thiazolidine-2-thioamide were obtained.

NMR (δ ppm, CDCl ₃ ): 1.2-2.2 (m, 12H), 2.2-2.9 (m, 2H), 3.25 (t, 4H, J =
7.0Hz), 3.9 (t, 2H, J = 6.0Hz), 4.5 (t, 2H, J = 7.0Hz),
6.32 (d, 1H, J = 6.0Hz), 6.55 (t, 1H, J = 8.0Hz), 6.8-
7.0 (m, 3H), 7.1-7.4 (m, 3H). Example 5 D of 5- (4-carboxyhexanylidene) -4-hydroxy-4-phenoxybutyl-2-cyclopentenone
-Synthesis of xylose (1-position) sugar ester Thiazolidine-2-thionamide 353 mg (0.75 mmol) and D-xylose 450 mg (3 mmol) in 8 ml dry pyridine solution dimethylaminopyridine 10 mg, NaH (60% in oil) 8 mg
Was added, and the mixture was stirred at room temperature for 2 hours. 10 drops of saturated ammonium chloride water was added, and pyridine was distilled off under reduced pressure. Extraction was performed by adding 15 ml of n-butanol, 5 ml of pH 7, 0.1M phosphate buffer. Further, it was extracted with n-butanol, and the organic layer was washed with saturated saline acidified with acetic acid. N-Butanol in the organic layer was distilled off under reduced pressure, and the obtained oily substance was subjected to silica gel column chromatography (CHCl ₃ : MeOH: AcOH: H ₂ O = 80: 5: 1: 0.5) to give 166 mg of sugar ester ( 44%).

NMR (δ ppm, CDCl ₃ ); 1.2-2.8 (m, 16H), 3.2-4.2 (m, 5H), 3.9 (t, 2H, J = 6.
0Hz), 3.6 (m, 1H), 5.1-6.0 (m, 4H), 6.3 (1H, d, J = 6.
0Hz), 6.55 (t, 1H, J = 8.0Hz), 6.7−7.0 (m, 3H), 7.1−
7.4 (m, 3H). IR (cm ^-1 , neat); 3400,2950,1740 (sh), 1720 (sh), 1700,1650,1600,159
0,1500. Example 6 D of 5- (4-carboxyhexanilidene) -4-hydroxy-4-phenoxybutyl-2-cyclopentenone
-Glucose (6-position) sugar ester synthesis Thiazolidine-2-thionamide 440 mg (0.93 mmol) and D-glucose 502 mg (2.8 mmol) were made into 10 ml dry pyridine solution, and dimethylaminopyridine 10 mg and NaH (60
% In oil) was added and stirred for 3 hours. After the reaction, 10 drops of aqueous NH ₄ Cl was added, and pyridine was distilled off under reduced pressure. Extraction was carried out by adding 10 ml of n-butanol, 5 ml of pH 7, 0.1 M phosphate buffer. The aqueous layer was further extracted with n-butanol, and the organic layer was washed with saturated saline acidified with acetic acid. N-Butanol in the organic layer was distilled off under reduced pressure, and the obtained oily substance was subjected to silica gel column chromatography (CHCl ₃ : MeOH: AcOH: H ₂ O = 80: 5: 2: 1) to give 165 mg of sugar ester ( 33%) and sugar ester with 2-mercaptothiazoline added to the 7-position 185 mg (28%)
Got

NMR (δ ppm, CDCl ₃ ); 1.2-2.8 (m, 16H), 3.1-4.8 (m, 14H), 6.25 (d, 1H, J =
6Hz), 6.5 (m, 1H), 6.7-7.0 (m, 3H), 7.1-7.4 (m, 3
H). IR (cm ⁻¹ , neat); 3400,2950,1740,1700,1655,1600,1585,1500. Example 7 5- (4-carboxy-2-hexenylidene) -4-hydroxy-4-phenoxybutyl-2 Of Cyclopentenone Thiazoline-2-Thionamide To 10 ml of 10 ml of a dry methylene chloride solution containing 610 mg (1.65 mmol) of carboxylic acid, 270 μl (1.92 mmol) of trimethylamine was added, cooled to −20 ° C. under N ₂ atmosphere, and 238 μ of pivaloyl chloride.
1 (1.92 mmol) was added and the mixture was stirred for 2 hours. Next, 202 mg (1.7 mmol) of 2-mercaptothiazoline and 21 mg (0.18 mmol) of dimethylaminopyridine were added, and the mixture was stirred at room temperature for 6 hours. About 10 ml of 0.5N HCl was added, and the mixture was extracted with methylene chloride. The organic layer was washed with sodium bicarbonate water and saturated saline, and then dried over anhydrous magnesium sulfate. After separation, the solvent was distilled off under reduced pressure, and the obtained oil was subjected to silica gel column chromatography (hexane: ethyl acetate = 1: 1 → 2: 3) to obtain 590 mg (76%) of thiazolidine-2-thionamide. .

NMR (δ ppm, CDCl ₃ ); 1.2-2.2 (m, 8H), 2.2-3.0 (m, 2H), 3.25 (t, 4H, J = 7.
0Hz), 3.9 (t, 2H, J = 6.0Hz), 4.5 (t, 2H, J = 7.0Hz), 6.
3-7.4 (m, 10H). Example 8 Synthesis of D-glucose (6-position) sugar ester of 5- (4-carboxy-2-hexenylidene) -4-hydroxy-4-phenoxybutyl-2-cyclopentenone Thiazolidine-2-thionamide 330 mg (0.7 mmol) and D
-Glucose 450 mg (2.5 mmol) in 10 ml dry pyridine solution, and at room temperature dimethylaminopyridine 10 mg, NaH (60%
in oil) 8 mg was added and stirred for 2 hours and a half. After the reaction, 10 drops of aqueous NH ₄ Cl was added, and pyridine was distilled off under reduced pressure. 10 ml of n-branol, pH 7, and 5 ml of 0.1 M phosphate buffer were added for extraction. The organic layer was washed with saturated saline acidified with acetic acid. N-Butanol in the organic layer was distilled off under reduced pressure, and the obtained oily product was subjected to silica gel column chromatography (CHCl ₃ : MeOH: AcOH: H ₂
O = 80: 5: 2: 1) to obtain 190 mg (40%) of sugar ester.

NMR (δ ppm, CDCl ₃ ): 1.2-2.8 (m, 12H), 3.1-4.8 (m, 14H), 6.3-7.4 (m, 10
H). Example 9 Synthesis of thiazolidine-2-thionamide of Δ7-prostaglandin A ₁ To a solution of 495 mg (1.48 mmol) of carboxylic acid in 10 ml of methylene chloride was added 230 μl (1.63 mmol) of triethylamine, and -20
Cool to ° C. 202 μl of pivaloyl chloride (1.6
(3 mmol) was added and stirred for 2 hours. Then 2-methylcaptothiazoline 185 mg (.55 mmol) and DMAP 20 mg (0.16
mmol) was added and the mixture was stirred at room temperature for 10 hours. The reaction was terminated with 0.5N HCl water, and the mixture was extracted with methylene chloride. Organic layer
The extract was washed with aqueous NaHCO ₃ and saturated aqueous NaCl, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting crude oily substance was subjected to silica gel column chromatography (hexane: ethyl acetate = 3: 2 → 1: 2) to obtain 395 mg (2%) of a thiazoline-2-thionamide derivative.

NMR (δppm, CDCl ₃ ): 0.9 (m, 3H), 1.1-2.0 (m, 14H), 2.1-2.4 (m, 2H), 3.2
5 (t, 2H, J = 8Hz), 3.30 (t, 2H, J = 8Hz), 4.1 (m, 2H),
4.6 (t, 2H, J = 8Hz), 5.45 (dd, 1H, J = 15Hz, 8Hz), 5.75
(Dd, 1H, J = 15Hz, 6Hz), 6.33 (dd, 1H, J = 6Hz, 2Hz), 6.6
(T, 1H = 7Hz), 7.35 (dd, 1H, J = 6Hz, 3Hz). Example 10 Synthesis of D-ribose (5-position) sugar ester of Δ7-prostaglandin A ₁ Thiazoline-2-thionamide 197 mg (0.45 mmol) and D
-In a solution of 270 mg (1.8 mmol) ribose in 10 ml dry pyridine
NaH (60% in oil) 4 mg and DMAP 4.5 mg were added, and the mixture was stirred at room temperature for 1.5 hours and a half. Aqueous ammonium chloride (10 drops) was added, pyridine was distilled off under reduced pressure, and 10 ml of n-butanol, pH 7, 0.1 M phosphate buffer (10 ml) was added for extraction. Extracted twice with n-butanol. The organic layer was washed with saturated saline acidified with acetic acid. The organic layer was depressurized as it was, and the solvent was distilled off, followed by silica gel column chromatography (CHCl ₃ : MeOH: AcOH:
H ₂ O = 80: 5: 1: 0.5) and 122 mg of D-ribose ester
(58%) was obtained.

_{NMR (δppm, CDCl 3);} 0.9 (m, 3H), 1.1-2.0 (m, 14H), 2.0-2.6 (m, 4H), 3.5
−5.2 (m, 12H), 5.3−5.9 (m, 2H), 6.35 (dd, 1H, J = 6H
z, 3Hz), 6.65 (t, 1H, J = 7Hz), 7.35 (dd, 1H, J = 6Hz, 3H
z). IR (neat, cm ^-1 ); 3400,2950,1730,1700,1640,1580. Example 11 Antitumor effect on leukemia cells p388 1 × 10 ⁶ p388 mouse leukemia cells were intraperitoneally administered to BDF and mice. . 5- (4-carboxybutynylidene) -4
After the transplantation of cancer cells with sugar ester of D-glucose of -hydroxy-4-phenoxybutyl-2-cyclopentenone 24
It was intraperitoneally administered for 5 days from the time. The survival days of the mice were measured and the survival rate (ILS%) was calculated.

Claims (5)

[Claims] 1. The following formula [I]: 2-Cyclopentenones represented by. 2. The 4-hydroxy-2-cyclopentenones according to claim ^1, wherein R ¹ in the above formula [I] is a monosaccharide residue. 3. The following formula [II] [Wherein R ² , n, X, Is the same as the above definition. ] The compound represented by the following formula [I] characterized by reacting with a saccharide in the presence of a basic compound A method for producing 2-cyclopentenones represented by: 4. The method for producing 2-cyclopentenones according to claim 4, wherein the basic compound used is pyridine, a catalytic amount of 4-dimethylaminopyridine (hereinafter referred to as DMAP), and sodium hydride. 5. The following formula [II] [Wherein R ² , n, X, Is the same as the above definition. ] 2-Cyclopentenones represented by: