111022-61-8Relevant articles and documents
Studies on Nucleosides: Part XIII - Synthesis and Antiviral Activity of Acyclic Analogues of Spongosine
Singh, P. K.,Saluja, Sunita,Pratap, Ram,George, C. X.,Bhakuni, D. S.
, p. 823 - 827 (2007/10/02)
6-Amino-9--2-methoxypurine (9), 6-amino-2-ethoxy-9-purine (10) and 6-amino-9-(2-hydroxyethoxymethyl)-2-methoxypurine (17) have been synthesized.Condensation of 2,6-dichloropurine (4) with 2-O-chloromethyl-1,3-di-O-benzylglycerol (5) furnishes the protected acyclic nucleosides 8 (yield 50percent) and 7 (yield 7percent).Amination of 7 and 8 affords 6 and 13 respectively.Treatment of 13 with sodium methoxide and ethoxide gives 11 and 12 respectively.Deblocking of 11 and 12 with Pd-C/H2 finally produces 9 and 10 respectively.Condensation of 4 with 1-O-benzyl-2-O-chloromethylethanediol gives 19 (yield 55percent) and 15 (yield 5percent).Amination of 19 affords 18 which on treatment with sodium methoxide furnishes 16.Deblocking of 16 with Pd-C/H2 gives 17.Compounds 9, 10, 11, 13 and 17 in combination with interferon inducer, mycoviral ds RNA, exhibit 16, 0, 16, 40 and 40percent enhancement of protection respectively against the semliki forest virus in Swiss albino mice.