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Solamargine aglycone 3,22 bit structural modification and in vitro Antitumor Activity
Author: ZouLianHua
Tutor: ZhuoChao；TangXiuZhen
School: East China University of Science and Technology
Course: Pharmaceutical Engineering
Keywords: Solamargine Antitumor 5 - fluorouracil Nef reaction Synthesis
CLC: TQ460.1
Type: Master's thesis
Year: 2012
Downloads: 26
Quote: 0
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Abstract
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Solamargine has good anti-tumor biological activity, and the analysis of the active Solamargine designed based on the chemical structure and may have synthesized a novel anti- tumor activity of lead compounds steroidal alkaloid 3p- hydroxy -16,21 - epoxy - 20S- methyl - ene progesterone -5 -22 amine . We acetate Dehydropregnenolone for raw materials, 16 and 17 -bit epoxidation 3 - hydroxy TBS protection , Kishner-Wolff-Huang reduction to give 3β- tert -butyl- dimethyl- siloxane -16 - hydroxy-5 , 17 (20E) - diene - androstane through active Mn02 oxidation of 3β- tert -butyl- dimethyl- siloxane -5,17 (20E) - diene -16 - progesterone , and then with Michael Jai CH3N02 happen to obtain 3β- tert- butyldimethylsilyl oxo-5 - ene -22 - nitro -16 - progesterone by sodium borohydride reduction obtained important intermediate compound 7,3 β- tert -butyl- dimethyl- siloxane -16β -hydroxy-5 - ene -20S- methyl -22 - nitro - pregnane , through Nef reaction compound 9,16 β, 21 - epoxy -20S- methyl-5 - ene -3β, 22β- pregnane - diol , 3,22 hydroxy further structural modification and testing derivatives in vitro anti -tumor activity. Intermediates and chemical structure of the target product through 1H NMR, 13C NMR, IR were characterized and discussed the main factors of each step reaction and its compounds stereochemistry .
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