5′-Norcarbocyclic analogues of furano[2,3-d]pyrimidine nucleosides

Author:

Matyugina Elena S.1,Logashenko Evgeniya B.2,Zenkova Marina A.2,Kochetkov Sergey N.1,Khandazhinskaya Anastasia L.1

Affiliation:

1. 1Engelhardt Institute of Molecular Biology, Russian Academy of Sciences, Vavilov Street 32, Moscow 119991, Russian Federation

2. 2Institute of Chemical Biology and Fundamental Medicine, Siberian Branch of Russian Academy of Sciences, 8 Lavrentiev Avenue, Novosibirsk 630090, Russian Federation

Abstract

Abstract5′-Norcarbocyclic analogues of furano[2,3-d]pyrimidine nucleosides as well as 5-bromo and 5-iodouracil derivatives were synthesized to evaluate their potential antitumor activity. The halogenated derivatives display no cytotoxicity with respect to all tested cells: KB-3-1 (human epidermoid carcinoma), HeLa (human cervical epithelioid carcinoma), HuTu-80 (human duodenal cancer), B16 (mouse melanoma), and MDCK (normal epithelial). The cytotoxicity of the non-halogenated furano[2,3-d]pyrimidine derivatives increases with the lengthening of the alkyl chain of the substituent from 45 to 60 μm for octyl to from 3 to 10 μm for dodecyl.

Publisher

Walter de Gruyter GmbH

Subject

Organic Chemistry

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