E 2-(1H-benzotriazol-1-yl)-3-(4-trifluoromethylphenyl)acrylonitrile | 288071-99-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: E 2-(1H-benzotriazol-1-yl)-3-(4-trifluoromethylphenyl)acrylonitrile
• 英文别名: (E)-2-(benzotriazol-1-yl)-3-[4-(trifluoromethyl)phenyl]prop-2-enenitrile
• CAS: 288071-99-8
• 化学式: C₁₆H₉F₃N₄
• 分子量: 314.269
• InChiKey: ADOPZXGUZYIYDL-UKTHLTGXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  54.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  E 2-(1H-benzotriazol-1-yl)-3-(4-trifluoromethylphenyl)acrylonitrile 在 硫酸 作用下， 反应 3.0h， 以79%的产率得到(E)-2-Benzotriazol-1-yl-3-(4-trifluoromethyl-phenyl)-acrylamide
  参考文献：
  名称：

  Synthesis and antimycobacterial activity of 3-aryl-, 3-cyclohexyl- and 3-heteroaryl- substituted-2-(1H(2H)-benzotriazol-1(2)-yl)prop-2-enenitriles, prop-2-enamides and propenoic acids. II

  摘要：

  A series of 32 3-aryl-, 3-cyclohexyl-, and 3-heteroaryl-substituted-2-(1H(2H)-benzotriazol-1(2)-yl)-prop-2-enenitriles, prop-2-enamides and propenoic acids, was synthesized as a part of our research in the antitubercular field, according to an international program with the Tuberculosis Antimicrobial Acquisition and Coordinating Facility (TAACF). This work reports the preparation and analytical and spectroscopic characterization (MS, UV, IR, H-1 NMR) of all compounds synthesized. Among these only a few compounds (E-4b,c, E-5a, E-7e and E-8d) were found to be endowed with modest growth inhibition of Mycobacterium tuberculosis. However, the obtained results allowed to acquire interesting structure-activity relationships. (C) 2002 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(01)01174-0
• 作为产物：
  描述：

  T406石油添加剂 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 60.0h， 生成 E 2-(1H-benzotriazol-1-yl)-3-(4-trifluoromethylphenyl)acrylonitrile
  参考文献：
  名称：

  Synthesis and antitubercular activity of 3-aryl substituted-2-(1H(2H)benzotriazol-1(2)-yl)acrylonitriles#1# Part of this work was presented as a poster communication at the 2nd European Symposium on Antimicrobial Agents, Hradec Kralove, Czech Republic, 1–4 July 1998.

  摘要：

  A series of 22 3-aryl substituted-2-(1H(2H)-benzotriazol-1(2)-yl)acrylonitriles was synthesized for a preliminary in vitro evaluation of antitubercular activity according to an international program with the Tuberculosis Antimicrobial Acquisition & Coordinating Facility (TAACF). This work reports the synthetic approach and analytical and spectroscopic characterization (UV, IR, H-1- and C-13-NMR) of all compounds synthesized. Several compounds showed an interesting activity in the preliminary screening with a percent growth inhibition of the virulent Mycobacterium tuberculosis between 40 and 99% at the concentration of 12.5 mu g/mL. The most effective derivatives E-5a and E-5e were also tested against M. avium in vitro. (C) 2000 Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(00)00144-6

文献信息

• Carta, Antonio; Sanna, Paolo; Bacchi, Alessia, Heterocycles, 2002, vol. 57, # 6, p. 1079 - 1090
  作者：Carta, Antonio、Sanna, Paolo、Bacchi, Alessia

  DOI：——

  日期：——
• Synthesis and antitubercular activity of 3-aryl substituted-2-(1H(2H)benzotriazol-1(2)-yl)acrylonitriles#1# Part of this work was presented as a poster communication at the 2nd European Symposium on Antimicrobial Agents, Hradec Kralove, Czech Republic, 1–4 July 1998.
  作者：Paolo Sanna、Antonio Carta、Mohammad E.Rahbar Nikookar

  DOI：10.1016/s0223-5234(00)00144-6

  日期：2000.5

  A series of 22 3-aryl substituted-2-(1H(2H)-benzotriazol-1(2)-yl)acrylonitriles was synthesized for a preliminary in vitro evaluation of antitubercular activity according to an international program with the Tuberculosis Antimicrobial Acquisition & Coordinating Facility (TAACF). This work reports the synthetic approach and analytical and spectroscopic characterization (UV, IR, H-1- and C-13-NMR) of all compounds synthesized. Several compounds showed an interesting activity in the preliminary screening with a percent growth inhibition of the virulent Mycobacterium tuberculosis between 40 and 99% at the concentration of 12.5 mu g/mL. The most effective derivatives E-5a and E-5e were also tested against M. avium in vitro. (C) 2000 Editions scientifiques et medicales Elsevier SAS.
• Synthesis and antimycobacterial activity of 3-aryl-, 3-cyclohexyl- and 3-heteroaryl- substituted-2-(1H(2H)-benzotriazol-1(2)-yl)prop-2-enenitriles, prop-2-enamides and propenoic acids. II
  作者：Paolo Sanna、Antonio Carta、Laura Gherardini、Mohammad Esmail Rahbar Nikookar

  DOI：10.1016/s0014-827x(01)01174-0

  日期：2002.1

  A series of 32 3-aryl-, 3-cyclohexyl-, and 3-heteroaryl-substituted-2-(1H(2H)-benzotriazol-1(2)-yl)-prop-2-enenitriles, prop-2-enamides and propenoic acids, was synthesized as a part of our research in the antitubercular field, according to an international program with the Tuberculosis Antimicrobial Acquisition and Coordinating Facility (TAACF). This work reports the preparation and analytical and spectroscopic characterization (MS, UV, IR, H-1 NMR) of all compounds synthesized. Among these only a few compounds (E-4b,c, E-5a, E-7e and E-8d) were found to be endowed with modest growth inhibition of Mycobacterium tuberculosis. However, the obtained results allowed to acquire interesting structure-activity relationships. (C) 2002 Elsevier Science S.A. All rights reserved.