1-(4-bromophenyl)-1H-1,2,3-triazole-4-carbonitrile | 82936-42-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-(4-bromophenyl)-1H-1,2,3-triazole-4-carbonitrile
• 英文别名: 1-(4-Bromophenyl)triazole-4-carbonitrile
• CAS: 82936-42-3
• 化学式: C₉H₅BrN₄
• 分子量: 249.069
• InChiKey: UIYNHTHJKZMFDS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(4-bromophenyl)-1H-1,2,3-triazole-4-carbonitrile 在 氯化亚砜 、 sodium hydroxide 作用下， 以 水 、 甲苯 为溶剂， 反应 10.0h， 生成 1-(4-bromophenyl)-1H-1,2,3-triazole-4-carbonyl chloride
  参考文献：
  名称：

  Discovery of a novel 6,7-disubstituted-4-(2-fluorophenoxy)quinolines bearing 1,2,3-triazole-4-carboxamide moiety as potent c-Met kinase inhibitors

  摘要：

  A series of 6,7-disubstituted-4-(2-fluorophenoxy)quinoline derivatives possessing 1,2,3-triazole-4-carboxamide moiety were designed, synthesized and evaluated for their in vitro cytotoxic activities against four typical cancer cell lines (A549, H460, HT-29, and MKN-45). Most compounds showed moderate-to-excellent antiproliferative activity. Compounds 32, 36, 37, 45, 51, and 52 were further examined for their inhibitory activity against c-Met kinase. The promising compound 37, with a c-Met IC50 value of 2.27 nM, was identified as a multitargeted receptor tyrosine kinase inhibitor. The analysis of their structure-activity relationships indicated that compounds with EWGs, especially chloro group, at 2-position on the phenyl ring (moiety B) have potent antitumor activity. (C) 2016 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2016.04.035
• 作为产物：
  描述：

  4-溴苯胺 在 盐酸 、 sodium nitrite 作用下， 以 水 为溶剂， 反应 12.0h， 生成 1-(4-bromophenyl)-1H-1,2,3-triazole-4-carbonitrile
  参考文献：
  名称：

  Discovery of a novel 6,7-disubstituted-4-(2-fluorophenoxy)quinolines bearing 1,2,3-triazole-4-carboxamide moiety as potent c-Met kinase inhibitors

  摘要：

  A series of 6,7-disubstituted-4-(2-fluorophenoxy)quinoline derivatives possessing 1,2,3-triazole-4-carboxamide moiety were designed, synthesized and evaluated for their in vitro cytotoxic activities against four typical cancer cell lines (A549, H460, HT-29, and MKN-45). Most compounds showed moderate-to-excellent antiproliferative activity. Compounds 32, 36, 37, 45, 51, and 52 were further examined for their inhibitory activity against c-Met kinase. The promising compound 37, with a c-Met IC50 value of 2.27 nM, was identified as a multitargeted receptor tyrosine kinase inhibitor. The analysis of their structure-activity relationships indicated that compounds with EWGs, especially chloro group, at 2-position on the phenyl ring (moiety B) have potent antitumor activity. (C) 2016 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2016.04.035

文献信息

• Derdour, A.; Benabdallah, T.; Merah, B., Bulletin de la Societe Chimique de France, 1990, # 1, p. 69 - 78
  作者：Derdour, A.、Benabdallah, T.、Merah, B.、Texier, F.

  DOI：——

  日期：——
• Addition dipolaire-1,3 aux olefines portant une substitution captodative: reactivite comparee des α et des β amino acrylnitriles vis a vis des arylazides.
  作者：F Texier、A Derdour、H Benhaoua、T Benabdellah、O Yebdri

  DOI：10.1016/s0040-4039(00)87214-7

  日期：1982.1