公开(公告)号：WO2015170336A1

公开(公告)日：2015-11-12

申请号：PCT/IN2015/000188

申请日：2015-04-29

Applicant: COUNCIL OF SCIENTIFIC & INDUSTRIAL RESEARCH

Inventor： GOGOI, Sanjib ,  BORUAH, Romesh Chandra ,  SAIKIA, Pallabi ,  ADDLAGATTA, Anthony ,  SADDANAPU, Venkateshwarlu

IPC: C07D233/54 ,  A61P35/00

CPC classification number: C07D233/54

Abstract: The present invention relates to microwave assisted facile Michael addition of benzimidazole and imidazole to steroidal α,β-unsaturated ketones under solvent-free condition to afford corresponding Michael adducts 16α-(1H-benzimidazol-1-yl)-pregnenolone acetate (1) and 16α-(1H-imidazol-1-yl)-pregnenolone acetate (2). Compound 1 showed in vitro cytotoxic activities almost comparable to the drug doxorubicin against cervical HeLa cancer cell line (compound 1, IC 50 = 8.3317, doxorubicin IC 50 = 7.8126), prostate DU 205 cancer cell line (compound 1, IC 50 = 12.0192, doxorubicin IC50 = 9.1194) and breast cancer MCF-7 cell line (compound 1, IC 50 = 8.2855, doxorubicin IC 50 = 7.5094).

Abstract translation: 本发明涉及在无溶剂条件下向类固醇α，β-不饱和酮的微波辅助迈克尔加成苯并咪唑和咪唑，得到相应的迈克尔加成物16α-（1H-苯并咪唑-1-基） - 孕烯醇酮乙酸酯（1）和 16α-（1H-咪唑-1-基） - 孕烯醇酮乙酸酯（2）。 化合物1显示体外细胞毒活性几乎与药物多柔比星对宫颈HeLa癌细胞系（化合物1，IC50 = 8.3317，多柔比星IC50 = 7.8126），前列腺DU 205癌细胞系（化合物1，IC50 = 12.0192，多柔比星IC50 = 9.1194）和乳腺癌MCF-7细胞系（化合物1，IC50 = 8.2855，多柔比星IC50 = 7.5094）。