Synthesis of 3beta, 7alpha, 11alpha-trihydroxy-pregn-21-benzylidene-5-en-20-one derivatives and their cytotoxic activities

Li-Hong Shan; Hong-Min Liu; Ke-Xue Huang; Gui-Fu Dai; Chen Cao; Rui-Jing Dong

doi:10.1016/j.bmcl.2009.10.019

Synthesis of 3beta, 7alpha, 11alpha-trihydroxy-pregn-21-benzylidene-5-en-20-one derivatives and their cytotoxic activities

Bioorg Med Chem Lett. 2009 Dec 1;19(23):6637-9. doi: 10.1016/j.bmcl.2009.10.019. Epub 2009 Oct 14.

Authors

Li-Hong Shan¹, Hong-Min Liu, Ke-Xue Huang, Gui-Fu Dai, Chen Cao, Rui-Jing Dong

Affiliation

¹ New Drug Research and Development Center of Zhengzhou University, Zhengzhou 450001, China.

PMID: 19864129
DOI: 10.1016/j.bmcl.2009.10.019

Abstract

A series of novel 3beta, 7alpha, 11alpha-trihydroxy-pregn-21-benzylidene-5-en-20-one derivatives were synthesized and characterized by NMR, HRMS. The pregnenolone (1) was first biotransformed by Mucor circinelloides var lusitanicus to 3beta, 7alpha, 11alpha-trihydroxy-pregn-5-en-20-one (3), then 3 was treated with various benzaldehydes to produce 3beta, 7alpha, 11alpha-trihydroxy-pregn-21-benzylidene-5-en-20-one derivatives. These derivatives showed remarkable activity against EC109 cells. The absolute configuration of 3 was also confirmed by signal-crystal X-ray analysis.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Antineoplastic Agents / chemical synthesis*
Antineoplastic Agents / chemistry
Antineoplastic Agents / pharmacology*
Cell Line, Tumor
Cell Proliferation / drug effects
Crystallography, X-Ray
Drug Screening Assays, Antitumor
Humans
Models, Molecular
Molecular Structure
Mucor / metabolism
Pregnenolone / analogs & derivatives*
Pregnenolone / chemical synthesis
Pregnenolone / chemistry
Pregnenolone / pharmacology
Structure-Activity Relationship

Substances

Antineoplastic Agents
Pregnenolone