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■ Reaction of Colchiceinamide with Phosgene and with Thiophosgene: Structures and Antitubulin Activity of Tetracyclic Oxazolones, Oxazolethiones and Thiazolones of the Colchicine Series

Anjum Muzaffar, Ernest Hamel, and Arnold Brossi*

*Natural Products Section, Laboratory of Structural Biology, NIDDK, National Instutute of Health, Bethesda, Maryland 20892, U.S.A.

Abstract

Colchiceinamide (5) on reaction with phosgene and thiophosgene in the presence of triethylamine afforded tetracyclic compounds (7) and (8) respectively. Treatment of oxazolethione (8) with sodium hydroxide afforded thiazolone (9). All three tetracyclic compounds had very high negative specific rotations, but none of them inhibited tubulin polymerization in vitro.