1-[2-hydroxy-4-(2-phosphono-ethyl)-cyclopentyl]-1H-[1,2,3]triazole-4-carboxylic acid methyl ester

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-[2-hydroxy-4-(2-phosphono-ethyl)-cyclopentyl]-1H-[1,2,3]triazole-4-carboxylic acid methyl ester
• 英文别名: 2-[(1S,3R,4R)-3-hydroxy-4-(4-methoxycarbonyltriazol-1-yl)cyclopentyl]ethylphosphonic acid
• 化学式: C₁₁H₁₈N₃O₆P
• 分子量: 319.254
• InChiKey: ZWFRDUGCTSOVLG-FXBDTBDDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  135
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1-[2-hydroxy-4-(2-phosphono-ethyl)-cyclopentyl]-1H-[1,2,3]triazole-4-carboxylic acid methyl ester 在 氨 作用下， 以 甲醇 为溶剂， 反应 14.0h， 以99%的产率得到{2-[3-(4-carbamoyl-[1,2,3]triazol-1-yl)-4-hydroxycyclopentyl]-ethyl}-phosphonic acid
  参考文献：
  名称：

  Synthesis of 1,2,3-triazolo-carbanucleoside analogues of ribavirin targeting an HCV in replicon

  摘要：

  The synthesis of carbocyclic and phosphonocarbocyclic analogues of ribavirin, an anti-HCV inhibitor, are described. Those compounds were evaluated against HCV but also against other important viruses in order to determine their spectrum of antiviral activity. Compounds 6 and 13 displayed a moderate IC50 against HIV-1 of 43.8 and 37 muM, respectively. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00349-3
• 作为产物：
  描述：

  anti-3-(Hydroxymethyl)-6-oxabicyclo<3.1.0>hexane 在 吡啶 、 正丁基锂 、 sodium azide 、 三甲基溴硅烷 、 sodium iodide 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 107.0h， 生成 1-[2-hydroxy-4-(2-phosphono-ethyl)-cyclopentyl]-1H-[1,2,3]triazole-4-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis of 1,2,3-triazolo-carbanucleoside analogues of ribavirin targeting an HCV in replicon

  摘要：

  The synthesis of carbocyclic and phosphonocarbocyclic analogues of ribavirin, an anti-HCV inhibitor, are described. Those compounds were evaluated against HCV but also against other important viruses in order to determine their spectrum of antiviral activity. Compounds 6 and 13 displayed a moderate IC50 against HIV-1 of 43.8 and 37 muM, respectively. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00349-3

文献信息

• Synthesis of 1,2,3-triazolo-carbanucleoside analogues of ribavirin targeting an HCV in replicon
  作者：Yoshio Saito、Vanessa Escuret、David Durantel、Fabien Zoulim、Raymond F. Schinazi、Luigi A. Agrofoglio

  DOI：10.1016/s0968-0896(03)00349-3

  日期：2003.8

  The synthesis of carbocyclic and phosphonocarbocyclic analogues of ribavirin, an anti-HCV inhibitor, are described. Those compounds were evaluated against HCV but also against other important viruses in order to determine their spectrum of antiviral activity. Compounds 6 and 13 displayed a moderate IC50 against HIV-1 of 43.8 and 37 muM, respectively. (C) 2003 Elsevier Ltd. All rights reserved.