A practical synthesis of 3-substituted delta 3,5(6)-steroids as new potential 5 alpha-reductase inhibitor

W Tian; Z Zhu; Q Liao; Y Wu

doi:10.1016/s0960-894x(98)00339-4

A practical synthesis of 3-substituted delta 3,5(6)-steroids as new potential 5 alpha-reductase inhibitor

Bioorg Med Chem Lett. 1998 Aug 4;8(15):1949-52. doi: 10.1016/s0960-894x(98)00339-4.

Authors

W Tian¹, Z Zhu, Q Liao, Y Wu

Affiliation

¹ Shanghai Institute of Organic Chemistry, Chinese Academy of Science, China.

PMID: 9873464
DOI: 10.1016/s0960-894x(98)00339-4

Abstract

A new and practical synthetic approach to 3-substituted delta 3,5(6)-Steroids, as potential 5 alpha-reductase inhibitor, is described. The key step involves Pd-catalyzed coupling reaction of steroid 3-enol 5H-3-oxo-octafluoropentanosulfonates. 3-Phenylacetylenyl substituted delta 3,5(6)-steroid 3g and 3-phosphate substituted delta 3,5(6)-steroid 3f in our synthesized compounds exhibited high 5 alpha-reductase inhibitory activity in vitro assay.

MeSH terms

5-alpha Reductase Inhibitors*
Enzyme Inhibitors / chemical synthesis*
Enzyme Inhibitors / chemistry
Enzyme Inhibitors / pharmacology
Steroids / chemical synthesis*
Steroids / chemistry
Steroids / pharmacology
Structure-Activity Relationship

Substances

5-alpha Reductase Inhibitors
Enzyme Inhibitors
Steroids