Synthesis of trisubstituted thiophenes designed as progesterone receptor modulator

✍ Scribed by Weiqin Jiang; James J. Fiordeliso; Xin Chen; Zhihua Sui

• Publisher: Journal of Heterocyclic Chemistry
• Year: 2006
• Tongue: English
• Weight: 327 KB
• Volume: 43
• Category: Article
• ISSN: 0022-152X
• DOI: 10.1002/jhet.5570430540

✦ Synopsis

When a known 2-[4-morpholino]-3-aryl-5-substituted thiophene, which showed moderate activity as a progesterone antagonist, was superimposed with a potent steroidal progesterone antagonist Org-33628, it showed a fair alignment in most parts of the molecules. According to the molecular modelling, displacement of the morpholine oxygen atom in the thiophene derivative with a carbonyl group would provide a better alignment with the C-3 carbonyl in Org-33628. Thus, a series of novel trisubstituted thiophenes bearing a cyclic ketone moiety was synthesized. Although these compounds only showed weak activities as progesterone receptor antagonists, all target compounds are novel and are fully characterized.