Synthesis of some nucleolipids

Abstract

Adenosine 5'-phosphate P-(2-oleamidoethyl) ester (I), P-(2-palmitamidoethyl) ester (II), P-(1-hexadecyl ester (III), P-(1-octadecyl) ester (IV) and P-(1-adamantyl) ester (V) were prepared by the reaction of N, O2', O3'-triacetyladenosine 5'-phosphate with appropriate hydroxy derivative in the presence of N,N'-dicyclohexylcarbodiimide followed by the action of ammonia. 2', 3'-O-Ethoxymethyleneadenosine 5'-phosphate P-(2-palmitamidoethyl) ester (IX) was prepared by the reaction of 2-chloro-4,5-dimethyl-2-oxo-1,3,2-dioxaphosphole (VI) with N-(2-hydroxyethyl)palmitamide (VII) and 2',3'-O-ethoxymethyleneadenosine (VIII) followed by the action of aqueous triethylamine. Adenosine 5'-phospho-(1-decyl)amidate (X) and adenosine 5'-phospho-(1-pentadecyl)amidate (XI) were prepared by the action of 1-decylamine and 1-pentadecylamine resp. on adenosine 5'-phosphate in the presence of N,N'-dicyclohexylcarbodiimide. The compounds I-VIII are not degraded by shake venom diesterase. The inhibition of the activity of adenylate cyclase is dependent on the length of the aliphatic chain involved.