3'-(4-dhlorophenyl-1,2,3-triazol-1-yl)-3'-deoxy-α-D-thymidine | 1352505-13-5

• 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: 3'-(4-dhlorophenyl-1,2,3-triazol-1-yl)-3'-deoxy-α-D-thymidine
• 英文别名: 1-[(2S,4S,5S)-4-[4-(4-chlorophenyl)triazol-1-yl]-5-(hydroxymethyl)tetrahydrofuran-2-yl]-5-methyl-pyrimidine-2,4-dione；1-[(2S,4S,5S)-4-[4-(4-chlorophenyl)triazol-1-yl]-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 1352505-13-5
• 化学式: C₁₈H₁₈ClN₅O₄
• 分子量: 403.825
• InChiKey: WWMWBLWTLDFTOG-XHSDSOJGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  110
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  5'-O-acetyl-3'-azido-3'-deoxythymidine 在 甲醇 、 copper(ll) sulfate pentahydrate 、 硫酸 、 氨 、 乙酸酐 、 sodium ascorbate 作用下， 以 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 32.0h， 生成 3'-(4-dhlorophenyl-1,2,3-triazol-1-yl)-3'-deoxy-α-D-thymidine
  参考文献：
  名称：

  Synthesis and inhibitory activity of thymidine analogues targeting Mycobacterium tuberculosis thymidine monophosphate kinase

  摘要：

  We report on Mycobacterium tuberculosis thymidine monophosphate kinase (TMPKmt) inhibitory activities of a series of new 3'- and 5'-modified thymidine analogues including alpha- and beta-derivatives. In addition, several analogues were synthesized in which the 4-oxygen was replaced by a more lipophilic sulfur atom to probe the influence of this modification on TMPKmt inhibitory activity. Several compounds showed an inhibitory potency in the low micromolar range, with the 5'-arylthiourea 4-thio-alpha-thymidine analogue being the most active one (K(i) = 0.17 mu M). This compound was capable of inhibiting mycobacteria growth at a concentration of 25 mu g/mL. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.10.021

文献信息

• Synthesis and inhibitory activity of thymidine analogues targeting Mycobacterium tuberculosis thymidine monophosphate kinase
  作者：Sara Van Poecke、Hélène Munier-Lehmann、Olivier Helynck、Matheus Froeyen、Serge Van Calenbergh

  DOI：10.1016/j.bmc.2011.10.021

  日期：2011.12

  We report on Mycobacterium tuberculosis thymidine monophosphate kinase (TMPKmt) inhibitory activities of a series of new 3'- and 5'-modified thymidine analogues including alpha- and beta-derivatives. In addition, several analogues were synthesized in which the 4-oxygen was replaced by a more lipophilic sulfur atom to probe the influence of this modification on TMPKmt inhibitory activity. Several compounds showed an inhibitory potency in the low micromolar range, with the 5'-arylthiourea 4-thio-alpha-thymidine analogue being the most active one (K(i) = 0.17 mu M). This compound was capable of inhibiting mycobacteria growth at a concentration of 25 mu g/mL. (C) 2011 Elsevier Ltd. All rights reserved.