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17-hydroxy c27 steroid compound and its synthesis and use

A technology of steroidal compounds and synthesis methods, which can be applied to medical preparations containing active ingredients, drug combinations, and pharmaceutical formulas, and can solve the problems of short growth cycles of yam plants

Inactive Publication Date: 2003-05-14
SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The genus Dioscorea has a short growth cycle, high yield, and is convenient for large-scale planting. Utilizing high-yield Diosgenin (Diosgenin) to synthesize Pennogenin is conducive to the full and rational utilization of resources. The method for synthesizing Pennogenin from Diosgenin has not been reported in the literature

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028]The following specific implementation methods will help to understand the present invention, but do not limit the content of the present invention. Example 1 3β-tert-butyldiphenylsilyloxy-16-(acetyl-1,2-ethanedithio)-26-acetoxy-chol

[0029] Synthesis of sterane-5(6), 16(17)-dien-22-one (2b)

[0030] Compound 1b 97mg was dissolved in 1ml CH 2 Cl 2 , add 23ul HSCH 2 CH 2 SH, then dropwise add 35ulBF 3 Et 2 O, after reacting at room temperature for 2h, add 0.2ml Ac 2 O, reacted for 30min, and the reaction ended. Add saturated NaHCO 3 solution, followed by solid NaHCO 3 Until no bubbles came out, extracted with ethyl acetate, and the organic phase was washed with saturated NaHCO 3 solution and saturated NaCl solution, MgSO 4 Dry, filter, evaporate the solvent under reduced pressure, and separate by flash column chromatography to obtain 67 mg (59.2%) of a colorless oil. C 49 h 68 o 5 S 2 Si; 828; [α] D 20 =+45° (C=0.055, CHCl 3 ); 1 H-NMR: ...

Embodiment 6

[0039] Example 6 Synthesis of 3β-tert-butyldiphenylsilyloxy pinanogenin (7b)

[0040] Dissolve 25mg 6b in 10ml MeOH, add 16mg K 2 CO 3 , react until the raw material disappears, then drip excess concentrated HCl, react for 20min, evaporate the organic solvent under reduced pressure, add water and ethyl acetate, wash the organic phase with saturated NaCl solution, MgSO 4 Dry, filter, evaporate the organic solvent under reduced pressure, and separate by flash column chromatography to obtain 22 mg (95.9%) of a white solid. C 43 h 60 o 4 Si; FW 668; 1H-NMR: 7.68 and 7.35 (10H, m, Ph), 5.12 (1H, d, J=4.8Hz, 6-H), 3.97 (1H, t, J=7.5Hz, 16H), 3.51 (2H, m , 26-H), 3.39 (1H, t, J = 11.0Hz, 3-H), 1.05 (9H, s, Bu), 1.00 (3H, s, 19-Me), 0.90 (3H, d, J = 7.2Hz, 21-Me), 0.80 (3H, d, J = 6.3Hz, 27-Me), 0.79 (3H, s, 18-Me); MS (EI): 668 (M + , 1.2%), 651 (M + -17, 9.4%), 611 (M + -57, 67.1%); IR: 3457, 1623.

Embodiment 7

[0041] Example 7 Synthesis of pinanogenin (7a)

[0042] Dissolve 96mg of 7b in 10ml of THF, add 0.22ml of TBAF (1M in THF), reflux until the starting material disappears, saturated NH 4 Quenched by Cl, extracted with ethyl acetate, the organic phase was washed with saturated NaCl solution, MgSO 4 Dry, filter, evaporate the organic solvent under reduced pressure, and separate by flash column chromatography to obtain 55 mg (89%) of a white solid. C 27 h 42 o 4 ;FW 430; 1 H-NMR: 5.36 (1H, d, J = 5.4Hz, 6-H), 3.98 (1H, t, J = 7.5Hz, 16H), 3.52 (2H, m, 26-H), 3.41 (1H, t , J=10.8Hz, 3-H), 1.03 (3H, s, 19-Me), 0.92 (3H, d, J=7.2Hz, 21-Me), 0.82 (3H, s, 18-Me), 0.81 (3H, d, J=6.3Hz, 27-Me); MS (EI): 430 (M + , 11.2%), 413 (M + -17, 23.5%), 412 (M + -18, 43.7%); IR: 3466, 1621. Example 8 3β, 26-diacetoxy-16-(acetyl-1,2-ethanedithio)-cholestane-5(6), 16(17)-diene

[0043] Synthesis of -22-one (2a)

[0044] Compound 1a 154mg was dissolved...

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Abstract

The present invention is one kind of 17-hydroxy C27 steroid compound and its synthesis and use. The synthesis process of the present invention is simple and suitable for industrial production in synthesizing pennogenin as well as dihydro pennogenin and OSW-1 aglycone analog.

Description

technical field [0001] The invention relates to a class of steroidal compounds with novel structures, a synthesis method of the compounds, and their use in synthesizing pinanogenin and its analogues and OSW-1 aglycon analogues. technical background [0002] Steroidal compounds with 17-hydroxyl have unique biological activity and medicinal value, such as marine natural product pyrazine bisteroid (Cephalostatine) (see J.Chem.Soc., Chem..Commun., 1988,865; ibid, 1988, 1440), the natural product Pannifolia saponin (OSW-1) (see Bioorg. & Med. Chem. Lett., 1997, 7, 633) and pinanoside in Yunnan Baiyao and Sichuan Baiyao series products. Pennogenin (Pennogenin) was first isolated from trillium by R.E.Marker et al. (see J.Arm.Chem.Soc., 1943, 65, 1248), and later found that many Liliaceae (Liliaceae) All plants contain this saponin, and the content in Paris plants is even more considerable. The main plant resources of the famous national medicine - Yunnan Baiyao series products ar...

Claims

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Application Information

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IPC IPC(8): A61P9/00A61P17/00
Inventor 田伟生许启海陈玲
Owner SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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