Synthesis and Investigation of Antiviral Activity of 3'-O-(Aminoalkyl)-thymidines and their Quaternary Ammonium Salts

Article abstract of DOI:10.1007/BF01277631

Alkylation of 5'-O-tritylthymidine with dialkylaminoalkyl chlorides in the presence of sodium hydride yields 3'-O-dialkylaminoalkyl-5'-O-tritythymidine derivatives 2 which were treated with an excess of iodomethane to afford the corresponding quaternary ammonium derivatives 3.Deprotected nucleosides 4 and 6 were obtained by refluxing 3 and 2, respectively, in 80percent acetic acid.When the compounds 2-4 and 6 were investigated for activity against HSV and HIV, the trityl derivatives 2a and 2c were found active against HSV. - Keywords.Nucleoside synthesis; Alkylation; 3'-O-dialkylaminoalkylthymidine; 3'-dialkylammoniumalkylthymidine; HIV-1; Herpes simplex virus.