Synthesis of the carbocyclic analogs of uracil nucleosides

Abstract

Abstract Treatment of the required hydroxyl derivatives of cis ‐3‐aminocyclopentanemethanol with 3‐ethoxyacryloyl isocyanate gave N ‐(3‐ethoxyacryloyl)‐ N ′‐[hydroxy‐ or dihydroxy(hydroxy‐methyl)cyclopentyl]ureas. Cyclization of the ureas in dilute sulfuric acid afforded high yields of the carbocyclic analogs of uridine, 2′‐deoxyuridine, and 3′‐deoxyuridine. The uridine and 3′‐deoxyuridine analogs were also obtained in good yields by cyclizing the ureas in concentrated aqueous ammonia. None of the three analogs showed activity in tests versus KB cells in culture or L1210 leukemia in vivo.