期刊
STEROIDS
卷 104, 期 -, 页码 214-219出版社
ELSEVIER SCIENCE INC
DOI: 10.1016/j.steroids.2015.10.006
关键词
Steroidal alkaloids; Solasodine; Diosgenin; 22-Hydroxyfurostan; Mitsunobu reaction; Birch reduction; Spirosola-1,4,6-trien-3-one
资金
- Shandong Provincial Natural Science Foundation [ZR2011CZ001]
- National Natural Science Foundation of China (NSFC) [81172956]
The synthesis of 1 alpha-hydroxysolasodine from diosgenin was attempted. The Pd/C catalyst mediated dehydrogenation of diosgenin generated the 1,4,6-trien-3-one (3), which was reacted with Ac2O in pyridine in the presence of a catalytic amount of POCl3 followed by hydrolysis to give the 22-hydroxyfurostan (4) in 65% yield. Conversion of the primary 26-OH group into the azide and simultaneously 22-OH dehydration were achieved in one step by Mitsunobu reaction. Treatment of the (25R)-26-azidofurosta-1,4,6,20(22)-tetraen-3-one (5) with chlorotrimethylsilane (TMSCl)/NaI/MeCN and cyclisation in situ provided the (22R,25R)-spirosola-1,4,6-trien-3-one (6) in good yield. Stereoselective and regioselective epoxidation of trienone (6) with 30% H2O2 and 5% NaOH in methanol gave the 1 alpha,2 alpha-epoxy-(22R,25R)-spirosola-4,6-dien-3-one (7). Birch reduction of the epoxide (7) with Li/NH3 in THF followed by the treatment with NH4Cl, however, failed to generate the expected 1 alpha-hydroxysolasodine, but provided a tetrahydrofuran ring opening product, (22S,25R)-1 alpha, 16 beta-dihydroxy-22,26-epiminocholest-4-en-3-one (8). Compounds 3 and 5-8 as well as solasodine were evaluated for their cell growth inhibitory activities against human prostate cancer PC3, human cervical carcinoma Hela, and human hepatoma HepG2 cells. At the concentration of 10 mu M, only epoxide 7 displayed moderate inhibitory rates towards these cells (40-54%). (C) 2015 Elsevier Inc. All rights reserved.
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