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Communication | Regular issue | Vol 41, No. 12, 1995, pp.2651-2656
Published online, 1st January, 1970
DOI: 10.3987/COM-95-7255
4',1'a-Methanocarbocyclic Adenosine Analogues as Potential Inhibitors of S-Adenosylhomocysteine Hydrolase

Lak S. Jeong, Victor E. Marquez,* Chong-Shen Yuan, and Ronald T. Borchardt

*Laboratory of Medicinal Chemistry, Developmental Therapeutics Program, Division of Cancer Treatment, National Cancer Institute, NIH, Bethesda, Maryland 20892, U.S.A.

Abstract

Cyclopropane-fused carbocyclic adenosine (4) and its 5’-carboxaldehyde analogue (5) were synthesized as potential inhibitors of S-adenosylhomocysteine hydrolase. The key bicyclo[3.1.0]hexane alcohol (8) was obtained from the optically pure cyclopentenone synthon (6), and attachment of the purine base was performed in a single step from the methylsulfonate ester of 8 (compound (9)). Both target compounds behaved as weak inhibitors of the hydrolase.