5-Alkynyl-2'-deoxyuridines: chromatography-free synthesis and cytotoxicity evaluation against human breast cancer cells

Bioorg Med Chem. 2007 Apr 15;15(8):3082-8. doi: 10.1016/j.bmc.2007.01.048.

Srinivasarao Meneni ¹, Ingo Ott, Craig D Sergeant, Adam Sniady, Ronald Gust, Roman Dembinski

Affiliations

Affiliation

1 Department of Chemistry and Center for Biomedical Research, Oakland University, 2200 N. Squirrel Rd., Rochester, MI 48309-4477, USA.

PMID: 17336074 DOI: 10.1016/j.bmc.2007.01.048

Abstract

Starting with 5-iodo-2'-deoxyuridine, a series of 5-alkynyl-2'-deoxyuridines (with n-propyl, cyclopropyl, 1-hydroxycyclohexyl, p-tolyl, p-tert-butylphenyl, p-pentylphenyl, and trimethylsilyl alkyne substituents) have been synthesized via the palladium-catalyzed (Sonogashira) coupling reaction followed by a simplified isolation protocol (76-94% yield). The cytotoxic activity of modified nucleosides against MCF-7 and MDA-MB-231 human breast Cancer cells has been determined in vitro. 5-Ethynyl-2'-deoxyuridine, the only nucleoside in the series containing a terminal acetylene, is the most potent inhibitor with IC(50) (microM) 0.4+/-0.3 for MCF-7 and 4.4+/-0.4 for MDA-MB-231.

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