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WO2016135749A1 - Dérivés d'acétate de diosgénine-isoxazole, procédé pour leur préparation et leur activité antifongique - Google Patents

Dérivés d'acétate de diosgénine-isoxazole, procédé pour leur préparation et leur activité antifongique Download PDF

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Publication number
WO2016135749A1
WO2016135749A1 PCT/IN2016/050062 IN2016050062W WO2016135749A1 WO 2016135749 A1 WO2016135749 A1 WO 2016135749A1 IN 2016050062 W IN2016050062 W IN 2016050062W WO 2016135749 A1 WO2016135749 A1 WO 2016135749A1
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Prior art keywords
diosgenin
dihydro
dehydro
formula
acetate
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Inventor
Archana Moni DAS
Manash Protim HAZARIKA
Purnajyoti DEKA BHUYAN
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Council of Scientific and Industrial Research CSIR
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Council of Scientific and Industrial Research CSIR
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
    • C07J71/0005—Oxygen-containing hetero ring
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/10—Antimycotics
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
    • C07J71/0036—Nitrogen-containing hetero ring
    • C07J71/0042—Nitrogen only
    • C07J71/0047—Nitrogen only at position 2(3)
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
    • C07J71/0036—Nitrogen-containing hetero ring
    • C07J71/0057—Nitrogen and oxygen
    • C07J71/0063—Nitrogen and oxygen at position 2(3)

Definitions

  • This invention relates to the synthesis of a novel class of Diosgenin acetate-isoxazole starting from Diosgenin and its relatives and their antifungal activities against plant pathogenic fungus Alternaria alternate.
  • the compound of formula A antifungal activities against plant pathogenic fungus Alternaria alternate prepared by the process of invention are found to have an overall yield 80% after purification.
  • the process of the present invention does not involve the use of any costly and environmentally toxic reagents and catalysts and has been developed using a non-toxic reagents under mild reaction conditions.
  • Isoxazoline derivatives of the steroid compounds solasodine and diosgenin [Prismetov, M. P.; Dzhiembaev, B. Zh.; Kiseleva, E. N.; Kharlamova, T. V., Seriya Khimicheskaya (2000), (3), Page No. 28-30.]
  • This article describes the method for the synthesis of isoxazolinosolasodine and diosgenin via reaction of steroid ketones with formamide in the presence of perchloric acid with structural formula as given below:
  • This document discloses antifungal activity of 22 derivatives of C-27 steroidal saponins and 6 steroidal sapogenins against Candida albicans, Candida glabrata, Candida krusei, Cryptococcus neoformans, and Aspergillus fumigates with the following structures.
  • This could be useful as potent antifungal inhibitors shown in Fig.4.
  • the present invention provides a compound of formula A
  • R2 OAc or OH
  • R C 6 H 5 or CH 3 .
  • diosgenin acetate -Isoxazoles exhibits good antifungal activity.
  • diosgenin 1 i. optionally hydrogenating diosgenin 1 to obtain dihydrodiosgenin lb;
  • step (v) mixing the solution of C-26-oxime-5,6 dehydro-diosgenin acetate or C-26-oxime-5,6 dihydro-diosgenin acetate obtained in step (v) with phenyl acetylene or methyl acetylene, base and sodium hypochlorite in DCM (dichloromethane) at the temperature ranging between 30-50 °C under nitrogen atmosphere followed by the stirring at the temperature ranging between 30-50 °C for the period of time 25-48 hr;
  • DCM dichloromethane
  • step (vi) adding water to the reaction mixture obtained in step (vi) then extracted with water immiscible solvent followed by washing the combined organic layer with water and brine;
  • step (viii) drying the organic layer obtained in step (vii) followed by evaporating the solvent and purifying by column chromatography to get (22P,25R)-3P-acetoxyfurost-5,6,-dehydro-26-substituted isoxazole or (22P,25R)-3P-acetoxyfurost-5,6,-dihydro-26- substituted isoxazole a compound of formula A;
  • base is selected from the group consisting of pyridine, triethylamine.
  • protic solvent selected from methanol, ethanol, isoporyl alcohol.
  • water immiscible solvent selected from the group consisting of ethyl acetate, dichlorome thane.
  • composition comprising an antifungal compound of formula A or a pharmaceutically acceptable salt thereof along with pharmaceutically acceptable excipients.
  • compound of formula A is used for treating or preventing a fungal infection against plant pathogenic fungus Alternaria alternate.
  • Step C Oxidation of the hydroxyl group on C-26 of E-ring manipulation of diosgenin acetate of formula 4, starting from C-26-ol-5,6 dehydro-diosgenin acetate and C-26-ol- 5,6 dihydro-diosgenin acetate of formula 3 and their relatives under a mild reaction conditions as per literature procedures;
  • Step D Oxime formation on C-26 of E-ring manipulation of diosgenin acetate of formula 5, starting from C-26-aldehyde-5,6 dehydro-diosgenin acetate and C-26- aldehyde-5,6 dihydro-diosgenin acetate of formula 4 and their relatives under a mild reaction conditions ie.
  • Step E Isoxazole formation on C-26 of E-ring manipulation of diosgenin acetate of formula 7, starting from C-26-oxime-5,6 dehydro-diosgenin acetate and C-26-oxime- 5,6 dihydro-diosgenin acetate of formula 5a and 5b and of formula 6, under a mild reaction conditions ie.
  • Step D Formation of oxime [Step D] on C-26 of E-ring manipulation of diosgenin acetate of formula 5 starting from C-26-aldehyde-5,6 dehydro-diosgenin acetate and C-26-aldehyde-5,6 dihydro-diosgenin acetate of formula 4 and their relatives under a mild reaction conditions ie. reaction of C-26-aldehyde-5,6 dehydro-diosgenin acetate and C-26-aldehyde-5,6 dihydro-diosgenin acetate of formula 4a and 4b with acetylene in presence of hydroxylamine hydrochloric acid, pyridine and ethanol.
  • FIGURE 1 Reagents and conditions: (a) Pyridine/ Acetic anhydride/40-90 °C/ recrystallize [MeOH/EtOH/PrOH] (b) NaBH 3 CN [in CH 3 COOH/ C 3 H 7 COOH / C 4 H 9 COOH (2-5 mL)]/ Inert gas atmosphere/30-60 hrs/20-30 °C/CH 2 C1 2 / Base/ purification by column chromatography (c) PCC/CaC0 3 /Silica/ CH 2 Cl 2 /30-60 °C/ 4-12 hrs/ purification by column chromatography (d) Hydroxylamine hydrochloric acid/ Pyridine/Ethanol/ 60-100 °C/H 2 0/ extract with ethyl acetate (e) DCM/Acetylene/ Triethylamine/ sodium hypochlorite/0-40 °C/ 20-48 hrs/Nit
  • FIGURE 2 General formula according to the claim 1 is given below (Formula 1, 2, 3, 4, 5, 6 and 7):
  • FIGURE 3 Formula of final compounds
  • the present invention is to provide a compound of formula A
  • R2 OAc or OH
  • R C 6 H 5 or CH 3 .
  • the representative compounds are selected from;
  • Step C Oxidation of the hydroxyl group on C-26 of E-ring manipulation of diosgenin acetate of formula 4, starting from C-26-ol-5,6 dehydro-diosgenin acetate and C-26-ol- 5,6 dihydro-diosgenin acetate of formula 3 and their relatives under a mild reaction conditions as per literature procedures.
  • Step D Oxime formation on C-26 of F-ring manipulation of diosgenin acetate of formula 5, starting from C-26-aldehyde-5,6 dehydro-diosgenin acetate and C-26- aldehyde-5,6 dihydro-diosgenin acetate of formula 4 and their relatives under a mild reaction conditions ie. reaction of C-26-aldehyde-5,6 dehydro-diosgenin acetate and C- 26-aldehyde- 5,6 dihydro-diosgenin acetate of formula 4a and 4b with acetylene in presence of hydroxylamine hydrochloric acid, pyridine and 95% ethanol. The reaction mixture was refluxed, the progress of the reaction was monitored by TLC and the mixture was cooled with ice, washed with water and extracted with ethyl acetate. The solvent was removed under reduced pressure to get the desired products 5.
  • Step E Isoxazole formation on C-26 of E-ring manipulation of diosgenin acetate of formula 7, starting from C-26-oxime-5,6 dehydro-diosgenin acetate and C-26-oxime- 5,6 dihydro-diosgenin acetate of formula 5a and 5b and of formula 6, under a mild reaction conditions ie.
  • Antifungal activity test was performed using the plant pathogenic fungus Alternaria alternate with the inhibition percentage 85 as depicted in the Fig.4 and Table 1 as determined by the standard antifungal activity test, viz., Poison Food Technique.
  • R2 OAc or OH
  • Rl OH
  • acetylated the diosgenin viz. 5,6 dehydro-diosgenin and 5,6 dihydro-diosgenin [Step A] to acetylated diosgenin of the formula 2a and 2b.
  • the compound of formula 7a and 7b antifungal activities against plant pathogenic fungus Alternaria alternate as shown in Fig.4 and Table 1.
  • Example 1 is given by way of illustration of the working of the invention in actual practice and should not be construed to limit the scope of the present invention in any way.
  • Example 1 is given by way of illustration of the working of the invention in actual practice and should not be construed to limit the scope of the present invention in any way.
  • Step A Hydrogenation of Diosgenin : Diosgenin 1, two grams in 100 ml of ethanol was hydrogenated at 45 psi using 500 mg of 5% Pd/C for a period of 10 h. The reaction mixture was filtered and alcohol was distilled off under reduced pressure to furnish the crude hydrogenated product which was purified by column chromatography over silica gel using petroleum ether and ethyl acetate as the eluent to furnish dihydro diosgenin compound lb in pure form of 95% yield.
  • Step B F-ring opening of Diosgenin acetate of formula 3: ((22 ⁇ ,2513 ⁇ 4)-3 ⁇ - acetoxyfurost-26-ol : lg NaBH 3 CN was added to a 1 g solution of diosgenin acetate 2a in acetic acid 3 ml under argon atmosphere and stirred for 60 hrs at (30 °C). After that CH 2 CI 2 was added and then Na 2 C0 3 solution. The aqueous phase was extracted with CH 2 CI 2 and the combined organic layer dried over anhydrous Na 2 S0 4 and evaporated to get the product. Then the residue was purified by column chromatography (30% ethyl acetate/hexane) to give pure product 3a (white gummy liquid) with the yield of 0.716 g, 71%.
  • Step C Oxidization of the formula 3 to aldehyde of formula 4:((22 ⁇ ,2513 ⁇ 4)-3 ⁇ - acetoxyfurost-26-al:
  • Step E Isoxazole derivative of Diosgenin acetate of formula 7: ((22 ⁇ ,2513 ⁇ 4)-3 ⁇ - acetoxyf urost-26- (5-pheny 1 (isoxazole (8a) :
  • Step A Hydrogenation of Diosgenin lb:
  • Diosgenin 1 two grams in 100 ml of ethanol was hydrogenated at 45 psi using 500 mg of 5% Pd/C for a period of 10 h.
  • the reaction mixture was filtered and alcohol was distilled off under reduced pressure to furnish the crude hydrogenated product which was purified by column chromatography over silica gel using petroleum ether and ethyl acetate as the eluent to furnish dihydro diosgenin compound lb in pure form of 95% yield.
  • Step B F-ring opening of Diosgenin acetate of formula 3 : ((22 ⁇ ,2513 ⁇ 4)-3 ⁇ - acetoxyfurost-26-ol) :
  • Step C Oxidization of the formula 3b to aldehyde of formula 4b: ((22 ,25R)-3 ⁇ - acetoxyfurost-26-al) :
  • Step D Oxime derivative of dihydrodiosgenin acetate of the formula 5: ((22 ,25R)-3 ⁇ -acetoxyfurost-26-oxime): A mixture of 4b, 0.196 g, hydroxylamine hydrochloric acid 0.14 g, pyridine 1 ml and 95% ethanol 20 ml at temperature 80 °C for 1 hr, the progress of the reaction was monitored by TLC. Then the mixture was cooled with ice, washed with water and extracted with ethyl acetate. The solvent was removed under reduced pressure. A white gummy liquid was obtained, 5b with the yield of O.lg (51%).
  • Step E Isoxazole derivative of dihydrodiosgenin acetate of formula 8b: ((22 P,25R)-3 ⁇ -dihydroacetoxyfurost-26-(5-phenyl)isoxazole 8b):
  • Step B F-ring opening of Diosgenin acetate of formula 2a : ((22 P,25R)-3 ⁇ - acetoxyfurost-26-ol) : lg NaBH 3 CN was added to a 0.31 g solution of diosgenin acetate 2a in butanoic acid 3 ml under helium atmosphere and stirred for 30 hrs at 30 °C(. After that CH 2 CI 2 was added and then Na 2 C0 3 solution. The aqueous phase was extracted with ethyl acetate and the combined organic layer dried over anhydrous Na 2 S0 4 and evaporated to get the product. Then the residue was purified by column chromatography (30% ethyl acetate/hexane) to give pure product 3a (white gummy liquid) with the yield of 0.13 g, 41%.
  • Step C Oxidization of the formula 3 to aldehyde of formula 4a: ((22 P,25R)-3 ⁇ - acetoxyfurost-26-al) :
  • Step D Oxime derivative of Diosgenin acetate of the formula 5a: ((22 p,25R)-3 ⁇ - acetoxyfurost-26-oxime) :
  • Step E Isoxazole derivative of Diosgenin acetate of formula 7 ((22 p,25R)-3 ⁇ - acetoxyfurost-26-isoxazole) :
  • Step A Hydrogenation of Diosgenin :
  • Diosgenin 1 two grams in 100 ml of ethanol was hydrogenated at 45 psi using 500 mg of 5% Pd/C for a period of 10 h.
  • the reaction mixture was filtered and alcohol was distilled off under reduced pressure to furnish the crude hydrogenated product which was purified by column chromatography over silica gel using petroleum ether and ethyl acetate as the eluent to furnish dihydro diosgenin compound lb in pure form of 95% yield.
  • Step B F-ring opening of Diosgenin acetate of formula 3b: ((22 ⁇ ,2513 ⁇ 4)-3 ⁇ - acetoxyfurost-26-ol :
  • PCC 0.273 g was added to a ice cold mixture of powdered CaC0 3 0.127 g, silica 1.0 g, and 3b, 0.70 g in CH 2 C1 2 of 25 mL at room temperature.
  • the reaction mixture was stirred for 12 hrs at 30 °C.
  • the reaction mixture was diluted with diethyl ether, 50.0 mL and poured through a short column containing aluminum oxide (neutral). The solvent was removed under vacuum. Then the residue was purified by column chromatography (10% ethyl acetate/hexane) to give pure product 4b with white solid of 0.42 g (60%), mp.124 °C.
  • Step D Oxime derivative of Diosgenin acetate of the formula 5b: ((22 ⁇ ,2513 ⁇ 4)-3 ⁇ - acetoxyf urost-26-oxime:
  • Step E Isoxazole derivative of Diosgenin acetate of formula 7b: ((22 ⁇ ,25 ⁇ )-3 ⁇ - acetoxyfurost-26-(5-methyl)isoxazole (7b):
  • Step B F-ring opening of Diosgenin of formula 3c : ((22 ⁇ ,2513 ⁇ 4)-3 ⁇ -hydroxyfurost- 26-01) :
  • PCC 0.273 g was added to a ice cold mixture of powdered CaC0 3 0.127 g, silica 1.0 g, and 3c, 0.8 g in CH 2 C1 2 of 25 mL at 30 °C.
  • the reaction mixture was stirred for 7 hrs at temperature 40 °C.
  • the reaction mixture was diluted with diethyl ether, 50.0 mL and poured through a short column containing aluminum oxide (neutral). The solvent was removed under vacuum. Then the residue was purified by column chromatography (10% ethyl acetate/hexane) to give pure product 4c with white solid of 0.6 g (75%), mp.124 °C.
  • Step D Oxime derivative of dehydrodiosgenin of the formula 5c: ((22 ⁇ ,2513 ⁇ 4)-3 ⁇ - hydroxyfurost-26-oxime):
  • Step E Isoxazole derivative of dehydrodiosgenin of formula 8c: ((22 p,25R)-3 ⁇ - dehydrohydroxyfurost-26-(5-phenyl)isoxazole 8c):
  • Step A Hydrogenation of Diosgenin :
  • Diosgenin 1 two grams in 100 ml of ethanol was hydrogenated at 45 psi using 500 mg of 5% Pd/C for a period of 10 h.
  • the reaction mixture was filtered and alcohol was distilled off under reduced pressure to furnish the crude hydrogenated product which was purified by column chromatography over silica gel using petroleum ether and ethyl acetate as the eluent to furnish dihydro diosgenin compound lb in pure form of 95% yield.
  • Step B F-ring opening of dihydrodiosgenin of formula 3d : ((22 P,25R)-3 ⁇ - hydroxyfurost-26-ol) :
  • Step C Oxidization of the formula 3d to aldehyde of formula 4d: ((22 p,25R)-3 ⁇ - hydroxyfurost-26-al) :
  • Step D Oxime derivative of dihydrodiosgenin of the formula 5d: ((22 P,25R)-3 ⁇ - acetoxyfurost-26-oxime) :
  • Step E Isoxazole derivative of dihydrodiosgenin of formula 8d ((22 ⁇ ,2513 ⁇ 4)-3 ⁇ - hydroxyfurost-26-isoxazole) :
  • Step B F-ring opening of Diosgenin of formula 3c : ((22 ⁇ ,2513 ⁇ 4)-3 ⁇ -hydroxyfurost- 26-01) :
  • Step C Oxidization of the formula 3c to aldehyde of formula 4c: ((22 ⁇ ,2513 ⁇ 4)-3 ⁇ - hydroxyfurost-26-al) :
  • PCC 0.273 g was added to a ice cold mixture of powdered CaC0 3 0.127 g, silica 1.0 g, and 3c, 0.5 g in CH 2 C1 2 of 25 mL at 30 °C.
  • the reaction mixture was stirred for 7 hrs at temperature 40 °C.
  • the reaction mixture was diluted with diethyl ether, 50.0 mL and poured through a short column containing aluminum oxide (neutral). The solvent was removed under vacuum. Then the residue was purified by column chromatography (10% ethyl acetate/hexane) to give pure product 4c with white solid of 0.32 g (64%), mp.124 °C.
  • Step D Oxime derivative of dehydrodiosgenin of the formula 5c: ((22 ⁇ ,2513 ⁇ 4)-3 ⁇ - hy droxyf urost-26-oxime) :
  • Step E Isoxazole derivative of dehydrodiosgenin of formula 7c: ((22 p,25R)-3 ⁇ - dehydrohydroxyfurost-26-(5-methyl)isoxazole 7c) :
  • Step A Hydrogenation of Diosgenin :
  • Diosgenin 1 two grams in 100 ml of ethanol was hydrogenated at 45 psi using 500 mg of 5% Pd/C for a period of 10 h.
  • the reaction mixture was filtered and alcohol was distilled off under reduced pressure to furnish the crude hydrogenated product which was purified by column chromatography over silica gel using petroleum ether and ethyl acetate as the eluent to furnish dihydro diosgenin compound lb in pure form of 95% yield.
  • Step B F-ring opening of dihydrodiosgenin of formula 3d : ((22 P,25R)-3 ⁇ - hydroxyfurost-26-ol) :
  • Step C Oxidization of the formula 3d to aldehyde of formula 4d: ((22 p,25R)-3 ⁇ - hydroxyfurost-26-al) :
  • Step D Oxime derivative of dihydrodiosgenin of the formula 5d: ((22 P,25R)-3 ⁇ - hydroxyfurost-26-oxime) :
  • Step E Isoxazole derivative of dihydrodiosgenin of formula 7d ((22 P,25R)-3 ⁇ - hydroxyfurost-26-isoxazole) :

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Abstract

La présente invention concerne une nouvelle classe d'acétate de diosgénine-isoxazole et la synthèse d'acétate de diosgénine-isoxazole à partir de diosgénine et de ses composés apparentés, par cinq (5) voies de synthèse : (A) acétylation, (B) ouverture du cycle F de l'acétate de diosgénine, (C) oxydation du groupe hydroxyle sur le C26 lors d'une manipulation du cycle E de l'acétate de diosgénine, (D) formation d'oxime et (E) formation d'isoxazole sur le C26 lors d'une manipulation du cycle E de l'acétate de diosgénine. Les dérivés de l'invention présentent une activité antifongique puissante contre le champignon Alternaria.
PCT/IN2016/050062 2015-02-23 2016-02-22 Dérivés d'acétate de diosgénine-isoxazole, procédé pour leur préparation et leur activité antifongique Ceased WO2016135749A1 (fr)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114634416A (zh) * 2022-04-14 2022-06-17 河北旭阳能源有限公司 一种2-氯-2-硝基丙烷的制备方法

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20080287662A1 (en) * 2005-06-22 2008-11-20 Zeev Wiesman Balanites Aegyptiaca Saponins and Uses Thereof

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20080287662A1 (en) * 2005-06-22 2008-11-20 Zeev Wiesman Balanites Aegyptiaca Saponins and Uses Thereof

Non-Patent Citations (8)

* Cited by examiner, † Cited by third party
Title
CHONG-REN YANG; YING ZHANG; MELISSA R. JACOB; SHABANA I. KHAN; YING-JUN ZHANG; XING-CONG LI, ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, vol. 50, no. 5, 2006, pages 1710 - 1714
HAMID A A ET AL: "Synthesis of novel anticancer agents through opening of spiroacetal ring of diosgenin", STEROIDS, ELSEVIER SCIENCE PUBLISHERS, NEW YORK, NY, US, vol. 87, 12 June 2014 (2014-06-12), pages 108 - 118, XP029009616, ISSN: 0039-128X, DOI: 10.1016/J.STEROIDS.2014.05.025 *
IRISMETOV, M. P.; GORYAEV, M. I.; MIRZASALIEVA, N. A.; RUSTEMBEKOVA, G. B: "Izvestiya Akademii Nauk Kazakhskoi SSR", SERIYA KHIMICHESKAYA, no. 5, 1982, pages 55 - 59
M.P. IRISMETOV; M. I, GORYAEV; G. YU. TSVETKOVA, RUSSIAN JOURNAL OF GENERAL CHEMISTRY, vol. 46, no. 6, 1976, pages 1407 - 1409
PRISMETOV, M. P.; DZHIEMBAEV, B. ZH.; KISELEVA, E. N.; KHARLAMOVA, T. V., SERIYA KHIMICHESKAYA, no. 3, 2000, pages 28 - 30
SINGH MONIKA ET AL: "Synthesis of diosgenin analogues as potential anti-inflammatory agents", JOURNAL OF STEROID BIOCHEMISTRY AND MOLECULAR BIOLOGY, ELSEVIER SCIENCE LTD., OXFORD, GB, vol. 143, 9 May 2014 (2014-05-09), pages 323 - 333, XP029016112, ISSN: 0960-0760, DOI: 10.1016/J.JSBMB.2014.04.006 *
SUBHASH CHANDRA; SARLA SAKLANI; ABHAY P. MISHRA, INTERNATIONAL JOURNAL OF HERBAL MEDICINE, vol. 1, no. 4, 2013, pages 67 - 70
YANG CHONG-REN ET AL: "Antifungal activity of C-27 steroidal saponins", ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, AMERICAN SOCIETY FOR MICROBIOLOGY, US, vol. 50, no. 5, 1 May 2006 (2006-05-01), pages 1710 - 1714, XP002602719, ISSN: 0066-4804, DOI: 10.1128/AAC.50.5.1710-1714.2006 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114634416A (zh) * 2022-04-14 2022-06-17 河北旭阳能源有限公司 一种2-氯-2-硝基丙烷的制备方法

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