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Issue 7, 2006
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Synthesis of 3′-β-carbamoylmethylcytidine (CAMC) and its derivatives as potential antitumor agents

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Abstract

3′-β-Carbamoylmethylcytidine (CAMC) and its derivatives were synthesized using an intramolecular Reformatsky-type reaction promoted by SmI2 as the key step. In vitro tumor cell growth inhibitory activity was evaluated and CAMC was found to exhibit potent cytotoxicity against various human tumor cell lines. From a structure–activity relationship study it was postulated that the cytotoxic mechanism of action of CAMC did not require phosphorylation at the 5′-hydroxyl group. This study provides a novel strategy for the development of a new type of antitumor nucleoside.

Graphical abstract: Synthesis of 3′-β-carbamoylmethylcytidine (CAMC) and its derivatives as potential antitumor agents

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Article information


Submitted
12 Dec 2005
Accepted
25 Jan 2006
First published
20 Feb 2006

Org. Biomol. Chem., 2006,4, 1284-1296
Article type
Paper

Synthesis of 3′-β-carbamoylmethylcytidine (CAMC) and its derivatives as potential antitumor agents

S. Ichikawa, N. Minakawa, S. Shuto, M. Tanaka, T. Sasaki and A. Matsuda, Org. Biomol. Chem., 2006, 4, 1284
DOI: 10.1039/B517602F

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