1,2-di-O-acetyl-3-O-mesyl-5-O-(methoxycarbonyl)-D-xylofuranose | 57024-70-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: 1,2-di-O-acetyl-3-O-mesyl-5-O-(methoxycarbonyl)-D-xylofuranose
• 英文别名: 1,2-di-0-acetyl-3-0-mesyl-5-0-methoxycarbonyl-D-xylofuranose；1,2-di-O-acetyl-3-O-mesyl-5-O-methoxycarbonyl-D-xylofuranose；[(3R,4S,5R)-2-acetyloxy-5-(methoxycarbonyloxymethyl)-4-methylsulfonyloxyoxolan-3-yl] acetate
• CAS: 57024-70-1
• 化学式: C₁₂H₁₈O₁₁S
• 分子量: 370.334
• InChiKey: DZQGHLSIMNHVNG-GZBOUJLJSA-N

物化性质

• 沸点：
  494.9±45.0 °C(Predicted)
• 密度：
  1.43±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  24
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  149
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  1,2-di-O-acetyl-3-O-mesyl-5-O-(methoxycarbonyl)-D-xylofuranose 在 氢溴酸 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 49.0h， 生成 1-<2-O-acetyl-3-O-mesyl-5-O-(methoxycarbonyl)-β-D-xylofuranosyl>-N4-acetylcytosine
  参考文献：
  名称：

  Nucleosides. 116. 1-(.beta.-D-Xylofuranosyl)-5-fluorocytosines with a leaving group on the 3' position. Potential double-barreled masked precursors of anticancer nucleosides

  摘要：

  Syntheses of five pairs of cytosine and 5-fluorocytosinexylofuranosyl nucleosides in which the 3'-hydroxyl group is replaced by Cl, Br, OMs, or OTs are described. Those xylosyl nucleosides with a good leaving group at the 3' position exhibit good inhibitory activity against L5178Y and P815 mouse leukemic cells in vitro at rather low concentrations, and like that of ara-C this cytotoxicity is reversed by 2'-deoxycytidine but not by thymidine. Xylosylcytosines are not active against ara-C resistant lines of L5178Y and P815 cells; however, the corresponding 5-fluorocytosine analogues exhibit significant cytotoxicity against these ara-C resistant leukemic cell lines, and this activity is reversed by thmidine but not by deoxycytidine. These data support the "double-barreled" masked precursor hypothesis in that xylosyl-5-fluorocytosines substituted at the 3' position by a good leaving group exhibit activity akin to that of ara-C in the ara-C sensitive lines, while these nucleosides act as 5-fluoropyrimidines in the ara-C resistant lines.

  DOI：

  10.1021/jm00184a006

文献信息

• 3'-azido purine nucleoside
  申请人：THE WELLCOME FOUNDATION LIMITED

  公开号：EP0421739A1

  公开（公告）日：1991-04-10

  The present invention relates to 3′-azido purine nucleosides of formula (I) and their use in medical therapy, particularly for the treatment or prophylaxis of human immunodeficiency virus and hepatitis B virus infections, to methods for their preparation and to compositions containing them. wherein R represents halogen; C₁₋₆ alkoxy; C₃₋₆ cycloalkoxy; aryloxy or arylalkoxy in which the aryl may optionally be substituted with C₁₋₆ alkyl, C₁₋₆ alkoxy, halogen, nitro or hydroxyl; amino which is substituted by one or two substituents indepently selected from C₁₋₆ alkyl, aryl, aralkyl including aracycloalkyl and C₃₋₆ cycloalkyl; or a 4- to 6- membered heterocyclic ring containing at least one nitrogen atom which ring is bonded to the purine base via a/the nitrogen atom; or a pharmaceutically acceptable derivative thereof.

  本发明涉及式(I)的3′-叠氮嘌呤核苷及其在医学治疗中的用途，特别是用于治疗或预防人类免疫缺陷病毒和乙型肝炎病毒感染，还涉及其制备方法和含有它们的组合物。 其中 R 代表卤素；C₁₋₆ 烷氧基；C₃₋₆ 环烷氧基；芳氧基或芳烷氧基，其中芳基可任选被 C₁₋₆ 烷基、C₁₋₆ 烷氧基、卤素、硝基或羟基取代；被一个或两个取代基取代的氨基，这些取代基独立地选自 C₁₋₆烷基、芳基、芳烷基（包括芳环烷基）和 C₃₋₆环烷基；或含有至少一个氮原子的 4-6 位杂环，该杂环通过一个氮原子与嘌呤基结合；或其药学上可接受的衍生物。
• WILSON, JEFFREY D.
  作者：WILSON, JEFFREY D.

  DOI：——

  日期：——
• US4921950A
  申请人：——

  公开号：US4921950A

  公开（公告）日：1990-05-01
• US5153318A
  申请人：——

  公开号：US5153318A

  公开（公告）日：1992-10-06