Enantioselective synthesis of new analogs of neplanocin A and their biological activity

Abstract Various carbocyclic nucleosides analogs of neplanocin A (such as 5-aminoimidazole-4-carboxamide riboside, uridine, 5-iodouridine, 4-thiouridine, cytidine, thymidine, 2′-deoxyguanosine, ribofuranosylthymine, a 2,2′-anhydroderivative, 2′-deoxycytidine, 2′-deoxythiouridine, and d -arabinofuranosylcytosine analogs) were synthesized from (1 R , 2 S , 3 R )-2,3-isopropylidenedioxy-4-methoxymethyloxymethyl-4-cyclopentenylamine. The cytidine analog was found the most active in inhibiting mouse lymphoma L5178Y cells in vitro at a concentration as low as 0.8 μg/mL.