Srivastava P C, Robins R K
J Med Chem. 1981 Oct;24(10):1172-7. doi: 10.1021/jm00142a010.
Oxazinomycin was converted into 2',3',5'-tri-O-acetyloxazinomycin (2) and 2',3'-O-isopropylideneoxazinomycin (3), respectively. Compound 3 was iodinated and reduced to provide 5'-deoxy-2',3'-O-isopropylideneoxazinomycin (5) which, after acid hydrolysis, provided 5'-deoxyoxazinomycin (6). Alternatively, the iodination of oxazinomycin followed by catalytic hydrogenation also provided 6. Oxazinomycin was treated with 2-acetoxybenzoyl chloride to provide 3'-O-acetyl-2'-chloro-2'-deoxyoxazinomycin (8) which, after reduction with tributyltin hydride, provided 3'-O-acetyl-2'-deoxyoxazinomycin (9). Oxazinomycin was also converted into oxazinomycin 5'-phosphate (10) and into O4,2'-anhydrooxazinomycin (11). 1,2,4-Oxadiazole-3,5-dione (12) was glycosylated to provide 2-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)-1,2,4-oxadiazole-3,5-dione (13) which, after deacetylation, provided 2-beta-D-ribofuranosyl-1,2,4-oxadiazole-3,5-dione (14). Similarly, 12 provided 2-(2-deoxy-beta-D-erythro-pentofuranosyl)-1,2,4-oxadiazole-3,5-dione (17); 14 was also converted into the corresponding 2',3'-O-isopropylidene derivative 15. Compound 14 showed significant antiviral activity against herpes simplex virus type 1, in vitro.
恶嗪霉素分别被转化为2',3',5'-三-O-乙酰基恶嗪霉素（2）和2',3'-O-异亚丙基恶嗪霉素（3）。化合物3经碘化和还原得到5'-脱氧-2',3'-O-异亚丙基恶嗪霉素（5），其经酸水解后得到5'-脱氧恶嗪霉素（6）。另外，恶嗪霉素经碘化后再进行催化氢化也得到6。恶嗪霉素用2-乙酰氧基苯甲酰氯处理得到3'-O-乙酰基-2'-氯-2'-脱氧恶嗪霉素（8），其用三丁基氢化锡还原后得到3'-O-乙酰基-2'-脱氧恶嗪霉素（9）。恶嗪霉素还被转化为恶嗪霉素5'-磷酸酯（10）和O4,2'-脱水恶嗪霉素（11）。1,2,4-恶二唑-3,5-二酮（12）经糖基化得到2-(2,3,5-三-O-乙酰基-β-D-呋喃核糖基)-1,2,4-恶二唑-3,5-二酮（13），其脱乙酰基后得到2-β-D-呋喃核糖基-1,2,4-恶二唑-3,5-二酮（14）。类似地，12得到2-(2-脱氧-β-D-赤式-戊呋喃糖基)-1,2,4-恶二唑-3,5-二酮（17）；14也被转化为相应的2',3'-O-异亚丙基衍生物15。化合物14在体外对1型单纯疱疹病毒显示出显著的抗病毒活性。
