4-Amino-1-((2R,3S,4R,5R)-3-hydroxy-5-hydroxymethyl-4-iodo-tetrahydro-furan-2-yl)-1H-pyrimidin-2-one; hydrochloride | 74580-89-5

• 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: 4-Amino-1-((2R,3S,4R,5R)-3-hydroxy-5-hydroxymethyl-4-iodo-tetrahydro-furan-2-yl)-1H-pyrimidin-2-one; hydrochloride
• CAS: 74580-89-5
• 化学式: C₉H₁₂IN₃O₄*ClH
• 分子量: 389.577
• InChiKey: VJRXXQSSESOIAM-NKCNMFRMSA-N

反应信息

• 作为产物：
  描述：

  Acetic acid (2R,3S,4S,5R)-5-acetoxymethyl-2-(4-acetylamino-2-oxo-2H-pyrimidin-1-yl)-4-iodo-tetrahydro-furan-3-yl ester 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 24.0h， 生成 4-Amino-1-((2R,3S,4R,5R)-3-hydroxy-5-hydroxymethyl-4-iodo-tetrahydro-furan-2-yl)-1H-pyrimidin-2-one; 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