Synthesis and Antiviral Evaluation of 3-Hydroxymethylpyrimido[1,6-c][1,3]oxazepine Derivatives
Year: 1998
Type: article
Abstract: A number of pyrimido[l,6-c][1,3]oxazepin derivatives, the anti dycosidic constrained acyclic analogs of uridine and cytidine have been preparedCompounds synthesized were evaluated for activity against herpes simplex virus type 1 (HSV-1) and human cytomegalovirus (HCMV).All of these compounds were inactive.From the initial discovery of a cyclonucleoside, 2',3'-0-i~oprop~lidene-0~,5-cyclocytidine by Todd and w-wokers' in 1951, a variety of derivatives of cyclonucleosides bridged by oxygen, sulfur, nitrogen and carbon have been prepared for several reasons.These include that cyclonucleosides are useful intermediates for nucleoside conversion, effective antileukemic agents, h d suitable probesc7 to study the relationship between substrate-inhibitor conformation and the specificities of the enzymes of nucleic acid biosynthesis.In the course of our research concerning new antitumor and antiviral agents,' " we have synthesized a new class of cyclonucleoside, namely anti-conformationally restricted pyrimidine acyclic nucleosides.We found 6-amino-3,3-bis(hydroxymethyl)-5-methyl-1H,3H,4H-pyrimido[l,6-c][1,3]oxzazine-8-one (I) had slight activity against H N 8 and 3-hydroxymetyl derivatives (II) of I showed slight activity against Breast Cancer cell line.l4 In order to explore potent antitumor and antiviral agents, we / HO I I1began to expand the six member oxazine ring to seven member oxazepin ring.We thought this ring
Source: Heterocycles
DOI: 10.3987/com-98-8280
Authors: Ling-Yih Hsu, Ya-Fun Kang, John C. Drach
Institutions: University of Michigan, National Defense Medical Center
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: diamond
OpenAlex ID: W4253133536