Abstract

ORGANIC PREPARATIONS AND PROCEDURES INT, 27 (2), 161-169 (1995) PHOSPHORYLATED ADENINE DERIVATIVES AS POTENTIAL SYNTHONS FOR ANTIVIRAL AGENTS Marwan El Masri and K. Darrell Berlin* Department of Chemistry, Oklahoma State Universiry, Stillwater, OK 74078 In studies directed towards the development of highly specific antiviral agents, we had need of certain N-phosphorylated adenine derivatives as potential synthons for such compounds. A search required were essentially of the literature revealed that N-phosphorylated adenines of the type we unknown. Our target systems were 1 and 2 both families of which possess highly reactive groups at the end of a chain attached at N(9). The rationale and incentive to include lad and 2a-d for synthesis were different from that for le and If. Compounds lad and 2a-d have excellent leaving groups at HNP(O)R 2 a) R = C~H,O, x = CI a) X = OP(O)(OPh)Ph I ".j b) R = 4-MeC&O, X = C1 5 :) b) X = OP(O)Ph2 c) R = C6H50, X = Ng C) X=N3 (N 2L d) R = 4-MeCgH40, X = N3 d) X=C1 Y 4 ,J 2' e) R = C6H50, X = NHCH2-3-C5bN 5 e) X=OH f) R = 4-MeC&@. X = NHCH2-4-C&N 2x the