NSC-744736 | 1186295-49-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: NSC-744736
• 英文别名: 2-phenyl-N-((1-(4-(trifluoromethyl)benzyl)-1H-1,2,3-triazol-4-yl)methyl)oxazole-4-carboxamide；ND-006730；RJP-I-22
• CAS: 1186295-49-7
• 化学式: C₂₁H₁₆F₃N₅O₂
• 分子量: 427.386
• InChiKey: VUYFTQAAKYHXJT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.93
• 重原子数：
  31.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  85.84
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  2-phenyl-N-(prop-2-ynyl)oxazole-4-carboxamide 、 4-trifluoromethylbenzyl azide 在 copper(II) sulfate 、 sodium ascorbate 作用下， 以 水 、 叔丁醇 为溶剂， 反应 96.0h， 生成 NSC-744736
  参考文献：
  名称：

  N-((1-Benzyl-1H-1,2,3-triazol-4-yl)methyl)arylamide as a New Scaffold that Provides Rapid Access to Antimicrotubule Agents: Synthesis and Evaluation of Antiproliferative Activity Against Select Cancer Cell Lines

  摘要：

  A series of N-((1-benzyl-1H-1,2,3-triazol-4-yl)methyl)arylamides was synthesized by copper-catalyzed azide alkyne cycloaddition (CuAAC) and afforded inhibitors of cancer cell growth. For example, compound 13e had an IC50 of 46 nM against MCF-7 human breast tumor cells. Structure activity relationship (SA R) studies demonstrated that (i) meta-phenoxy substitution of the N-1-benzyl group is important for antiproliferative activity and (ii) a variety of heterocyclic substitutions for the aryl group of the arylamide are tolerated. In silico COMPARE analysis of antiproliferative activity against the NCI-60 human tumor cell line panel revealed a correlation to clinically useful antimicrotubule agents such as paclitaxel and vincristine. This in silico correlation was supported by (i) in vitro inhibition of tubulin polymerization, (ii) G(2)/M-phase arrest in HeLa cells as assessed by flow cytometry, and (iii) perturbation of normal microtubule activity in HeLa cells as observed by confocal microscopy. The results demonstrate that N-((1-benzyl-1H-1,2,3-triazol-4-yl)methyl)arylamide is a readily accessible small molecule scaffold for compounds that inhibit tubulin polymerization and tumor cell growth.

  DOI：

  10.1021/jm1000979