1-(2,3,5-tri-O-acetyl-β-L-arabinofuranosyl)-4-(1,2,4-triazole-1-yl)-1H-pyridinium-2-one | 160946-66-7

• 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-(2,3,5-tri-O-acetyl-β-L-arabinofuranosyl)-4-(1,2,4-triazole-1-yl)-1H-pyridinium-2-one
• CAS: 160946-66-7
• 化学式: C₁₇H₁₉N₅O₈
• 分子量: 421.367
• InChiKey: WLVWKXFSZYCKGR-HNKHHVNMSA-N

物化性质

• 沸点：
  605.5±65.0 °C(Predicted)
• 密度：
  1.56±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.85
• 重原子数：
  30.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  153.73
• 氢给体数：
  0.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  1-(2,3,5-tri-O-acetyl-β-L-arabinofuranosyl)-4-(1,2,4-triazole-1-yl)-1H-pyridinium-2-one 在 ammonium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 48.0h， 以87%的产率得到阿扎胞苷杂质20
  参考文献：
  名称：

  Synthesis of 1-β-L-Arabinofuranosylcytosine (β-L-Ara-C) and 2′-Deoxy-2′-methylene-β-L-cytidine (β-L-DMDC) as Potential Antineoplastic Agents

  摘要：

  1-beta-L-Arabinofuranosylcytosine (beta-L-Ara-C, 7) and 2'-deoxy-2'-methylene-beta-L-cytidine (beta-L-DMDC, 14) have been synthesized via a multi-step synthesis from L-arabinose. These compounds were tested in vitro against L1210, P388, Sarcoma 180, and CEM cells, and found not to be active at a concentration up to 100 mu M. beta-L-Ara-C and beta-L-DMDC were also tested against HSV-1 and HSV-2 and yielded ID50 values of >100 mu M.

  DOI：

  10.1080/15257779408010669
• 作为产物：
  描述：

  1-(β-L-arabinofuranosyl)uracil 在 4-氯苯基二氯磷酸酯 作用下， 以 吡啶 为溶剂， 反应 72.0h， 生成 1-(2,3,5-tri-O-acetyl-β-L-arabinofuranosyl)-4-(1,2,4-triazole-1-yl)-1H-pyridinium-2-one
  参考文献：
  名称：

  Synthesis of 1-β-L-Arabinofuranosylcytosine (β-L-Ara-C) and 2′-Deoxy-2′-methylene-β-L-cytidine (β-L-DMDC) as Potential Antineoplastic Agents

  摘要：

  1-beta-L-Arabinofuranosylcytosine (beta-L-Ara-C, 7) and 2'-deoxy-2'-methylene-beta-L-cytidine (beta-L-DMDC, 14) have been synthesized via a multi-step synthesis from L-arabinose. These compounds were tested in vitro against L1210, P388, Sarcoma 180, and CEM cells, and found not to be active at a concentration up to 100 mu M. beta-L-Ara-C and beta-L-DMDC were also tested against HSV-1 and HSV-2 and yielded ID50 values of >100 mu M.

  DOI：

  10.1080/15257779408010669