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Paper | Regular issue | Vol 89, No. 7, 2014, pp.1606-1619
Published online, 12th May, 2014
DOI: 10.3987/COM-14-12999
The Synthesis and Evaluation of New Carbocyclic Pyrrolo[2,3-d]pyrimidine Nucleoside Analogs

Jongbok Lee, Hyewon Seo, Sangeun Yoon, Kowoon Choi, Chul-Hoon Lee,* and Hakjune Rhee*

*Chemistry and Applied Chemistry, Department of Bionanotechnology, Hanyang University, 1271 Sa-3-dong, Sangrok-gu, Ansan, Kyunggi-do, 426-791, Korea

Abstract

New carbocyclic pyrrolo[2,3-d]pyrimidine nucleoside analogs were synthesized with the key intermediate, 4-amino-6-bromo-5-cyanopyrrolo[2,3-d]pyrimidine (2), by SN2 reaction. One of the products, 4-amino-6-bromo-1-cyclopentyl-1H-pyrrolo[2,3-d]pyrimidine-5-carboxamide (9), showed significant anti-proliferative activity to the human ovarian cancer PA-1 cells (IC50: 3.9 μM). Based on the biological effects and the functional group characteristics of the compound 9, other carbocyclic nucleoside analogs related to the compound 9 were synthesized with key intermediate 2 by a Pd(0)-catalyzed coupling reaction. As expected, syn-4-amino-6-bromo-7-[4-(methoxymethyl)-2-cyclopenten-1-yl]-7H-pyrrolo[2,3-d]pyrimidine-5-carboxamide (15) showed very similar anti-proliferative activity (IC50: 2.6 μM) when compared to compound 9.