Rusjakovski B, Kobe J, Brdar B, Japelj M, Valcavi U
Farmaco Sci. 1982 Nov;37(11):764-80.
2-(1-Isopropylidene)azino-3-beta and 3-alpha-D-arabinofuranosyl-5-methoxycarbonylmethylenethiazolidine-4-ones (III) and (IV) have been synthesized by condensation of benzylated alpha-chloro-D-arabinofuranose (V) with o-(trimethylsilyl)-2-(1-isopropilidene)azino-5-methoxycarbonylmethylen- thiazolidine-4-one (VI) in the presence of SnCl4 or molecular sieves. Condensation of benzoylated alpha, beta-bromo-D-arabinose (VII) with (VI) led exclusively to the alpha anomer (VIII). 2-(1-Isopropylidene)azino-3-alpha-D-arabinofuranosyl-5-carbamoylmethylene- thiazolidine-4-one (IX) has been synthesized from (IV) (R, R1, R2 = CH3). 1H-N.M.R. and 13C-N.M.R. data confirmed the structures of (III) and (IV) (R, R1, R2 = CH3 and R, R1 = CH3, R2 = Ph). Antiviral activities were tested on monolayer cultures of KB-cells. Whereas previously tested beta-D-ribofuranosyl derivatives had moderate activity, alpha and/or beta-D-arabinofuranosyl derivatives are totally inactive against herpes simplex and poliovirus.
通过苄基化的α-氯-D-阿拉伯呋喃糖（V）与邻（三甲基硅基）-2-（1-异亚丙基）叠氮基-5-甲氧羰基亚甲基噻唑烷-4-酮（VI）在四氯化锡或分子筛存在下缩合，合成了2-（1-异亚丙基）叠氮基-3-β和3-α-D-阿拉伯呋喃糖基-5-甲氧羰基亚甲基噻唑烷-4-酮（III）和（IV）。苯甲酰化的α，β-溴-D-阿拉伯糖（VII）与（VI）缩合仅生成α-异头物（VIII）。由（IV）（R，R1，R2 = CH3）合成了2-（1-异亚丙基）叠氮基-3-α-D-阿拉伯呋喃糖基-5-氨甲酰基亚甲基噻唑烷-4-酮（IX）。1H-N.M.R.和13C-N.M.R.数据证实了（III）和（IV）（R，R1，R2 = CH3以及R，R1 = CH3，R2 = Ph）的结构。在KB细胞单层培养物上测试了抗病毒活性。虽然先前测试的β-D-核糖呋喃糖基衍生物具有中等活性，但α和/或β-D-阿拉伯呋喃糖基衍生物对单纯疱疹病毒和脊髓灰质炎病毒完全无活性。
