2-Alkylsulfanyl estrogen derivatives: synthesis of a novel class of multi-targeted anti-tumour agents

Mathew P Leese; Simon P Newman; Atul Purohit; Michael J Reed; Barry V L Potter

doi:10.1016/j.bmcl.2004.04.027

2-Alkylsulfanyl estrogen derivatives: synthesis of a novel class of multi-targeted anti-tumour agents

Bioorg Med Chem Lett. 2004 Jun 21;14(12):3135-8. doi: 10.1016/j.bmcl.2004.04.027.

Authors

Mathew P Leese¹, Simon P Newman, Atul Purohit, Michael J Reed, Barry V L Potter

Affiliation

¹ Medicinal Chemistry, Department of Pharmacy and Pharmacology and Sterix Ltd, University of Bath, Bath BA2 7AY, UK.

PMID: 15149660
DOI: 10.1016/j.bmcl.2004.04.027

Abstract

A flexible, direct, high yielding synthesis of 2-alkylsulfanyl estrogens from estrone has been developed. 2-Methylsulfanyl estradiol (2-MeSE2) 7 displays a similar anti-proliferative activity to the established 2-methoxyestradiol (2-MeOE2) 1, whilst its 3-O-sulfamate derivative (2-MeSE2MATE) 9 exhibits greatly enhanced anti-proliferative activity, combined with significant inhibition of steroid sulfatase, an enzyme target for the treatment of hormone-dependent tumours.

Publication types

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

MeSH terms

Antineoplastic Agents / administration & dosage
Antineoplastic Agents / chemical synthesis*
Cell Line, Tumor
Drug Delivery Systems / methods*
Estrogens / administration & dosage
Estrogens / chemistry*
Humans
Sulfuric Acid Esters / administration & dosage
Sulfuric Acid Esters / chemistry

Substances

Antineoplastic Agents
Estrogens
Sulfuric Acid Esters