5-[(4-decyl)-1,2,3-triazol-1-yl]methyl-3',5'-di-O-acetyl-2'-deoxyuridine | 1450644-73-1

• 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: 5-[(4-decyl)-1,2,3-triazol-1-yl]methyl-3',5'-di-O-acetyl-2'-deoxyuridine
• CAS: 1450644-73-1
• 化学式: C₂₆H₃₉N₅O₇
• 分子量: 533.625
• InChiKey: QHVNGWZORRMHMN-RBZQAINGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.64
• 重原子数：
  38.0
• 可旋转键数：
  15.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  147.4
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  5-[(4-decyl)-1,2,3-triazol-1-yl]methyl-3',5'-di-O-acetyl-2'-deoxyuridine 在 tri(1H-1,2,4-triazol-1-yl)phosphine oxide 、 氨 、 水 作用下， 以 1,4-二氧六环 、 乙腈 为溶剂， 反应 14.0h， 以32%的产率得到5-[(4-decyl)-1,2,3-triazol-1-yl]methyl-2′-deoxycytidine
  参考文献：
  名称：

  Inhibition of Mycobacterium tuberculosis strains H37Rv and MDR MS-115 by a new set of C5 modified pyrimidine nucleosides

  摘要：

  Two sets of pyrimidine nucleoside derivatives bearing extended alkyloxymethyl or alkyltriazolidomethyl substituents at position 5 of the nucleobase were synthesized and evaluated as potential antituberculosis agents. The impact of modifications at 3'- and 5'-positions of the carbohydrate moiety on the antimycobacterial activity and cytotoxicity was studied. The highest effect was shown for 5-dodecyloxymethyl-2'-deoxyuridine, 5-decyltriazolidomethyl-2'-deoxyuridine, and 5-dodecyltriazolidomethyl-2'-deoxycytidine. They effectively inhibited the growth of two Mycobacterium tuberculosis strains in vitro, laboratory H37Rv (MIC99 = 20, 10, and 20 mu g/mL, respectively) and clinical MDR MS-115 resistant to five top antituberculosis drugs (MIC99 = 50, 10, and 10 mu g/mL, respectively). (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.07.003
• 作为产物：
  描述：

  3',5'-di-O-acetyl-5-bromomethyl-2'-deoxyuridine 在 sodium azide 、 copper(ll) sulfate pentahydrate 、 sodium ascorbate 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.0h， 生成 5-[(4-decyl)-1,2,3-triazol-1-yl]methyl-3',5'-di-O-acetyl-2'-deoxyuridine
  参考文献：
  名称：

  Inhibition of Mycobacterium tuberculosis strains H37Rv and MDR MS-115 by a new set of C5 modified pyrimidine nucleosides

  摘要：

  Two sets of pyrimidine nucleoside derivatives bearing extended alkyloxymethyl or alkyltriazolidomethyl substituents at position 5 of the nucleobase were synthesized and evaluated as potential antituberculosis agents. The impact of modifications at 3'- and 5'-positions of the carbohydrate moiety on the antimycobacterial activity and cytotoxicity was studied. The highest effect was shown for 5-dodecyloxymethyl-2'-deoxyuridine, 5-decyltriazolidomethyl-2'-deoxyuridine, and 5-dodecyltriazolidomethyl-2'-deoxycytidine. They effectively inhibited the growth of two Mycobacterium tuberculosis strains in vitro, laboratory H37Rv (MIC99 = 20, 10, and 20 mu g/mL, respectively) and clinical MDR MS-115 resistant to five top antituberculosis drugs (MIC99 = 50, 10, and 10 mu g/mL, respectively). (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.07.003