First synthesis and structural report on selenophen-2-yl containing pnictogens: Biological activities of tris(selenophen-2-yl)stibine

Abstract

A new tertiary stibine and bismuthine containing C-heterocyclic selenophene ring have been synthesized. Tris(2-selenophenyl)stibine (1) and tris(2-selenophenyl) bismuthine (2) and characterized by IR, MS, H-1, C-13, COSY, HETCOR NMR spectroscopy. Crystal structures of stibine and bismuthine have been determined. In an attempted synthesis of tris(2-selenophenyl) phosphine, an oxidative product tris(2-selenophenyl) phosphine oxide (3) was isolated under the experimental conditions used, whose X-ray crystal structure was also determined. To best of our knowledge C-heterocyclic selenophene-2-yl pnictogens are first of their kind, as not many examples are known even with other p-block metal/metalloids. The biological activity of compound (1) was determined. The compound (1) shows a significant selectivity (> 85%) for carcinogenic cell K and U growth inhibition. The toxicity of tris(selenophen-2-yl) stibine (1) on larvae of Artemia Salina was studied and the LC50 value was 589.6 mu M. (c) 2005 Elsevier B.V. All rights reserved.