1-(3-chloro-3-deoxy-β-D-xylofuranosyl)cytosine hydrochloride | 74580-88-4

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 1-(3-chloro-3-deoxy-β-D-xylofuranosyl)cytosine hydrochloride
• CAS: 74580-88-4
• 化学式: C₉H₁₂ClN₃O₄*ClH
• 分子量: 298.126
• InChiKey: ZODAPGJDBHBRFR-NKCNMFRMSA-N

反应信息

• 作为产物：
  描述：

  1-(2,5-di-O-acetyl-3-chloro-3-deoxy-β-D-xylofuranosyl)-N⁴-acetylcytosine 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以1%的产率得到1-(3-chloro-3-deoxy-β-D-xylofuranosyl)cytosine hydrochloride
  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