Steride, its systhesis method and use

A technology of steroidal compounds and synthetic methods, applied in the field of synthesizing natural product OSW-1 sapogenin, which can solve the problems of resource waste, serious environmental pollution, and obsolete degradation process

Inactive Publication Date: 2003-03-26
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

[0014] Obviously, this synthesis strategy using steroidal sapogenins has many disadvantages, such as outdated degradation process, cumbersome operation steps, serious environmental pollution, etc., and more importantly, the carbon skeleton and functional groups of steroidal sapogenins have not been fully utilized. , which will inevitably result in a great waste of resources

Method used

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  • Steride, its systhesis method and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Example 1 Synthesis of 3β-hydroxyl-26,26-diphenylthiofurostane-5(6)-ene (14a)

[0043] Dissolve Diosgenin 10.000g (24.2mmol) in 100ml CH 2 Cl 2 In, add PhSH12.38ml (121.13mmol, 5.0eq), then slowly add BF 3 Et 2 O 6.11ml (48.6mmol, 2.0eq), stirred at room temperature until the raw material disappeared, added ethyl acetate to dilute, the organic phase was washed with 2N NaOH solution, and then washed with saturated NaCl solution until neutral, MgSO 4 Dry, filter, evaporate the solvent under reduced pressure, and separate by flash column chromatography to obtain 13.138 g (88.3%) of a white solid. C 39 h 52 o 2 S 2 , FW616; [α] D 17 =-45.1° (C=0.89, CHCl 3 ); mp 53-54°C; 1 H-NMR: 7.49-7.24 (10H, m, Ar), 5.37 (1H, d, J=4.2Hz, 6-H), 4.50 (1H, d, J=3.0Hz, 26-H), 4.27 (1H , m, 16-H), 3.52 (1H, m, 3-H), 3.24 (1H, m, 22-H), 1.17 (3H, d, J=6.6Hz, 21-Me), 1.05 (3H, s, 19-Me), 0.95 (3H, d, J=6.6Hz, 27-Me), 0.80 (3H, s, 18-Me); MS (EI): 507 (M + -109, 66.9%), 271 (1...

Embodiment 2

[0044] Example 2 Synthesis of 3β-hydroxyfurostane-5(6)-ene (15)

[0045] Dissolve 11.000g of 14a in 440ml of anhydrous EtOH, add about 30g of W-2 type Raney Ni, reflux until the raw material disappears, filter, the residue is fully washed with anhydrous EtOH, and the filtrate is spin-dried to obtain 6.653g (93.1%) of a white solid . C 27 h 44 o 2 , FW 400; [α] D 17 =-61.7° (C=1.01, CHCl 3 ); mp 69-70°C; 1 H-NMR: 5.34 (1H, d, J = 5.4Hz, 6-H), 4.30 (1H, m, 16-H), 3.52 (1H, m, 3-H), 3.31 (1H, m, 22- H), 1.02 (3H, s, 19-Me), 0.99 (3H, d, J = 7.2Hz, 21-Me), 0.89 (6H, d, J = 6.6Hz, 26, 27-Me), 0.81 ( 3H, s, 18-Me); MS (EI): 400 (M + ), 271 (100%); IR: 3381, 1052.

Embodiment 3

[0046] Example 3 Synthesis of 6β-acetoxy-3α, 5α-cyclofurostane (16)

[0047] Dissolve 1.111g of 15 in 5ml of dry pyridine, add 2.448g of TsCl under ice-cooling, react at room temperature until the raw material disappears, add ethyl acetate to dilute, wash the organic phase four times with saturated NaCl solution, MgSO 4 Dry, filter, and evaporate the solvent under reduced pressure. The obtained crude product was dissolved in 200ml of acetone, 3.5g of KOAc was added in 10ml of aqueous solution, refluxed until the raw material disappeared, the organic solvent was evaporated under reduced pressure, the organic matter was extracted with ethyl acetate, the organic phase was washed with saturated NaCl solution, MgSO 4 Dry, filter, and evaporate the solvent under reduced pressure. The obtained crude product was dissolved in 10ml Ac 2 O and 1ml of pyridine, add a small amount of DMAP, react at room temperature for 4h, and the reaction is complete. Add saturated NaHCO 3 solu...

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Abstract

A kind of compound, synthesizing method and its use is disclosed in the invention, whose structure formula is 1:R1=OH, OAc, OMs, OTs, OTBS, OTBDPS etc. or R1, R2 forming 3,5-three-membered ring structure; R2=x, or R1, R2 forming 1,5-three-membered ring structure, or R2, R3 forming 5,6-double bonds; R3=OH, OAc, OMs, OTs, OTBS, OTBDPS X etc. or R2, R3 forming 5,6-double bonds; R4=H, OH, SPh, S(CH2)nSA etc. or R4, R5 forming carbonic bonds, or R4, R5=S(CH2)nS, (n=2,3, etc.), or R5, R6 forming 16, 17 double bonds, or R5, R7 forming 16, 22 aether bond; R6=H, or R5, R6 forming 16, 17 double bonds; R5, R7 forming 16, 22 aether bond, or R7, R8 forming carbonic bonds; R5=H or R7, R8 forming carbonic bonds. Thereinto, Ac is acetyl, Ms is methylsulfonyl, Ts is toluenesulfonyl, TBS is butyl dimethylsilyl, TBDSPS is butyl dipheny Si-based, X is halogen, SPh is phenylthio.

Description

technical field [0001] The present invention relates to a class of steroidal compounds with novel structures, a synthesis method of such compounds and their use in the synthesis of natural product OSW-1 sapogenin. technical background [0002] In 1992, the Y.Sashida research group of the Faculty of Medicine, University of Tokyo isolated a series of saponins with a cholesterol skeleton from the underground corm of an evergreen ornamental plant Ornithogalum saunderside native to South Africa, which are only in the 3-position of the aglycone It is slightly different from the 2”-position of diglycoside, and both have strong anti-tumor activity. OSW-1, as the main extract, has strong lethality to a variety of malignant tumor cells, which is better than the current clinically used Several anticancer drugs such as Mitomycin (Mitomycin), Adriamycin (Adriamycin), Paclitaxel (Taxol), etc. are 10-100 times more effective. More importantly, although OSW-1 is effective against a variety ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J9/00
Inventor 田伟生许启海彭小文
Owner SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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