Regio- and stereoselective synthesis of 2'-β-substituted-fluoroneplanocin A analogues as potential anticancer agents
Akshata Nayak1, Pramod K Sahu, Jayoung Song
1Research Institute of Pharmaceutical Sciences, College of Pharmacy, Seoul National University, Seoul 151-742, Korea. lakjeong@snu.ac.kr.
Abstract:
A series of 2'-β-substituted-6'-fluoro-cyclopentenyl-pyrimidines and -purines 8 and 9 were successfully synthesized from d-ribose in a regio- and stereoselective manner. The functionalization at the C2-position of 6'-fluoro-cyclopentenyl nucleosides was achieved via regioselective protection of a hydroxyl group at the C3-position and stereoselective formation of C2-triflate followed by direct SN2 reaction with a fluoro or azido nucleophile. All the synthesized compounds were evaluated for their anticancer activities in several tumor cell lines, but were found to be neither active nor toxic.
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