2-(naphth-1-yl)-5-cyanobenzimidazole | 174648-23-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(naphth-1-yl)-5-cyanobenzimidazole
• 英文别名: 2-naphthalen-1-yl-3H-benzimidazole-5-carbonitrile
• CAS: 174648-23-8
• 化学式: C₁₈H₁₁N₃
• 分子量: 269.305
• InChiKey: LZOGOMQDKBYDCD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  52.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(naphth-1-yl)-5-cyanobenzimidazole 在 aluminum nickel 甲酸 作用下， 以 硝基苯 为溶剂， 反应 6.0h， 生成 2'-(naphth-1-yl)-5-cyano-2,5'-bi-1H-benzimidazole
  参考文献：
  名称：

  Substituted 2,5‘-Bi-1H-benzimidazoles:  Topoisomerase I Inhibition and Cytotoxicity

  摘要：

  Several 2'-aryl-5-substituted-2,5'-bi-1H-benzimidazole derivatives were synthesized and evaluated as topoisomerase I poisons and for their cytotoxicity toward the human lymphoblast cell line RPMI 8402. This study focused on 18 2,5'-bi-1H-benzimidazole derivatives which contained either a 5-cyano, a 5-(aminocarbonyl), or a 5-(4-methylpiperazinyl) group. Among these bibenximidazoles, the pharmacological activity of 2'-phenyl derivatives and the influence of the different positional isomers of either a 2'-tolyl group or a 2'-naphthyl moiety on cytotoxicity and topoisomerase I inhibitory activity were determined.

  DOI：

  10.1021/jm950412w
• 作为产物：
  描述：

  4-氨基-3-硝基苯甲腈 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 、 硝基苯 为溶剂， 145.0 ℃ 、310.27 kPa 条件下， 反应 1.5h， 生成 2-(naphth-1-yl)-5-cyanobenzimidazole
  参考文献：
  名称：

  Substituted 2,5‘-Bi-1H-benzimidazoles:  Topoisomerase I Inhibition and Cytotoxicity

  摘要：

  Several 2'-aryl-5-substituted-2,5'-bi-1H-benzimidazole derivatives were synthesized and evaluated as topoisomerase I poisons and for their cytotoxicity toward the human lymphoblast cell line RPMI 8402. This study focused on 18 2,5'-bi-1H-benzimidazole derivatives which contained either a 5-cyano, a 5-(aminocarbonyl), or a 5-(4-methylpiperazinyl) group. Among these bibenximidazoles, the pharmacological activity of 2'-phenyl derivatives and the influence of the different positional isomers of either a 2'-tolyl group or a 2'-naphthyl moiety on cytotoxicity and topoisomerase I inhibitory activity were determined.

  DOI：

  10.1021/jm950412w

文献信息

• [EN] ARYL HYDROCARBON RECEPTOR ACTIVATORS<br/>[FR] ACTIVATEURS DU RÉCEPTEUR D'HYDROCARBURE ARYLE
  申请人：UNIV OREGON STATE

  公开号：WO2021022061A1

  公开（公告）日：2021-02-04

  Small molecule AhR ligands are disclosed. The ligands can induce the differentiation of Tr1 cells to suppress pathogenic immune responses without inducing nonspecific immune suppression. Methods of treatment of autoimmune diseases using the AhR ligands are also disclosed.

  披露了小分子AhR配体。这些配体可以诱导Tr1细胞分化，抑制病原免疫反应，而不引起非特异性免疫抑制。还披露了使用AhR配体治疗自身免疫疾病的方法。
• Substituted 2,5‘-Bi-1<i>H</i>-benzimidazoles:  Topoisomerase I Inhibition and Cytotoxicity
  作者：Jung Sun Kim、Barbara Gatto、Chiang Yu、Angela Liu、Leroy F. Liu、Edmond J. LaVoie

  DOI：10.1021/jm950412w

  日期：1996.1.1

  Several 2'-aryl-5-substituted-2,5'-bi-1H-benzimidazole derivatives were synthesized and evaluated as topoisomerase I poisons and for their cytotoxicity toward the human lymphoblast cell line RPMI 8402. This study focused on 18 2,5'-bi-1H-benzimidazole derivatives which contained either a 5-cyano, a 5-(aminocarbonyl), or a 5-(4-methylpiperazinyl) group. Among these bibenximidazoles, the pharmacological activity of 2'-phenyl derivatives and the influence of the different positional isomers of either a 2'-tolyl group or a 2'-naphthyl moiety on cytotoxicity and topoisomerase I inhibitory activity were determined.