(E)-2-Benzotriazol-1-yl-3-(3-fluoro-phenyl)-acrylonitrile

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并三唑类
• 英文名称: (E)-2-Benzotriazol-1-yl-3-(3-fluoro-phenyl)-acrylonitrile
• 英文别名: (E)-2-(benzotriazol-1-yl)-3-(3-fluorophenyl)prop-2-enenitrile
• 化学式: C₁₅H₉FN₄
• 分子量: 264.262
• InChiKey: ACJSVJSAHREJGG-UKTHLTGXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• 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：
  4

反应信息

• 作为产物：
  描述：

  1H-苯并三唑-1-乙腈 、 3-氟苯甲醛 在 三乙胺 作用下， 以 甲苯 为溶剂， 反应 20.0h， 以72.5%的产率得到(E)-2-Benzotriazol-1-yl-3-(3-fluoro-phenyl)-acrylonitrile
  参考文献：
  名称：

  Synthesis and antiproliferative activity of 3-aryl-2-(1H-benzotriazol-1-yl)acrylonitriles. Part III

  摘要：

  A new series of 30 3-aryl-2-(1H-benzotriazol-1-yl)acrylonitriles were synthesized and tested for biological activity as part of our research in the antimicrobial and antitumor fields. In particular, title compounds were evaluated in vitro against representative strains of Gram-positive and Gram-negative bacteria (S. aureus, Salmonella spp), mycobacteria (M. fortuitum, M. smegmatis ATCC 19420 and M. tuberculosis ATCC 27294), yeast and mould (C. albicans ATCC 10231 and A. fumigatus). Furthermore, their antiretroviral activity against HIV-1 was determined in MT-4 cells together with cytotoxicity. In these assays title compounds and 47 additional derivatives described previously (P. Sanna, A. Carta, M.E. Rahbar Nikookar, Eur. J. Med. Chem. 35 (2000) 535-543; P. Sanna, A. Carta, L. Gherardini, M.E. Rahbar Nikookar, Farmaco 57 (2002) 79-87) were tested for their capability to prevent MT-4 cell growth. All compounds resulted devoid of antibacterial, antifungal and anti-HIV-1 activity. In anti-mycobacterial assays several compounds resulted active (MIC50 = 6.0-70 muM) against M. tuberculosis. However, since they showed cytotoxicity against MT-4 cells at lower concentrations (CC50 = 0.05-25 muM), their anti-mycobacterial activity was not selective. For this reason, the most cytotoxic compounds were also evaluated for antiproliferative activity against a panel of human cell lines derived from both hematological and solid tumors. Compound 34 resulted the most potent compound against the above human tumor-derived cell lines. (C) 2002 Published by Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(02)01411-3

文献信息

• Synthesis and antiproliferative activity of 3-aryl-2-(1H-benzotriazol-1-yl)acrylonitriles. Part III
  作者：Antonio Carta、Paolo Sanna、Michele Palomba、Laura Vargiu、Massimiliano La Colla、Roberta Loddo

  DOI：10.1016/s0223-5234(02)01411-3

  日期：2002.11

  A new series of 30 3-aryl-2-(1H-benzotriazol-1-yl)acrylonitriles were synthesized and tested for biological activity as part of our research in the antimicrobial and antitumor fields. In particular, title compounds were evaluated in vitro against representative strains of Gram-positive and Gram-negative bacteria (S. aureus, Salmonella spp), mycobacteria (M. fortuitum, M. smegmatis ATCC 19420 and M. tuberculosis ATCC 27294), yeast and mould (C. albicans ATCC 10231 and A. fumigatus). Furthermore, their antiretroviral activity against HIV-1 was determined in MT-4 cells together with cytotoxicity. In these assays title compounds and 47 additional derivatives described previously (P. Sanna, A. Carta, M.E. Rahbar Nikookar, Eur. J. Med. Chem. 35 (2000) 535-543; P. Sanna, A. Carta, L. Gherardini, M.E. Rahbar Nikookar, Farmaco 57 (2002) 79-87) were tested for their capability to prevent MT-4 cell growth. All compounds resulted devoid of antibacterial, antifungal and anti-HIV-1 activity. In anti-mycobacterial assays several compounds resulted active (MIC50 = 6.0-70 muM) against M. tuberculosis. However, since they showed cytotoxicity against MT-4 cells at lower concentrations (CC50 = 0.05-25 muM), their anti-mycobacterial activity was not selective. For this reason, the most cytotoxic compounds were also evaluated for antiproliferative activity against a panel of human cell lines derived from both hematological and solid tumors. Compound 34 resulted the most potent compound against the above human tumor-derived cell lines. (C) 2002 Published by Editions scientifiques et medicales Elsevier SAS.