title: Regio- and stereoselective synthesis of 2'-β-substituted-fluoroneplanocin A analogues as potential anticancer agents.
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.
authors.affiliation: Research Institute of Pharmaceutical Sciences, College of Pharmacy, Seoul National University, Seoul 151-742, Korea. lakjeong@snu.ac.kr.
authors.forename: Akshata
authors.initials: A
authors.lastname: Nayak
authors.forename: Pramod K
authors.initials: PK
authors.lastname: Sahu
authors.forename: Jayoung
authors.initials: J
authors.lastname: Song
authors.forename: Sang Kook
authors.initials: SK
authors.lastname: Lee
authors.forename: Lak Shin
authors.initials: LS
authors.lastname: Jeong
mesh_terms: D000241:Adenosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D045744:Cell Line, Tumor; D060326:Chemistry Techniques, Synthetic; D006801:Humans; D013237:Stereoisomerism
chemical_list: D000970:Antineoplastic Agents; C470754:fluoroneplanocin A; D000241:Adenosine