4-Benzoimidazol-1-ylmethyl-benzoic acid hydrazide | 870766-46-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 4-Benzoimidazol-1-ylmethyl-benzoic acid hydrazide
• 英文别名: 4-(1h-Benzimidazol-1-ylmethyl)benzoic acid hydrazide；4-(benzimidazol-1-ylmethyl)benzohydrazide
• CAS: 870766-46-4
• 化学式: C₁₅H₁₄N₄O
• 分子量: 266.302
• InChiKey: JPOLHBVWMOTBSG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  72.9
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-Benzoimidazol-1-ylmethyl-benzoic acid hydrazide 、 cycloheptatriene-maleic anhydride adduct 在 N,N-二异丙基乙二胺 作用下， 以 乙醇 为溶剂， 反应 6.0h， 生成 N-(3,3a,4,4a,5,5a,6,6a-octahydro-1,3-dioxo-4,6-ethenocycloprop[f]isoindol-2-(1H)-yl)-4-((1H-benzo[d]imidazol-1-yl)methyl)benzamide
  参考文献：
  名称：

  Tricyclononene carboxamide derivatives as novel anti-HIV-1 agents

  摘要：

  By modifying the chemical structure of anti-orthopoxvirus compound ST-246, we designed and synthesized a series of tricyclononene carboxamide derivatives and tested their anti-HIV-1 activity and cytotoxicity. We found that benzoimidazol-containing compound 7g was highly effective in inhibiting HIV-1 R5 infection with an IC50 value of 0.41 mu M and a selectivity index of 292, but it exhibited no significant inhibitory activity on HIV-1 reverse transcriptase, integrase and protease. CoMFA was used to analyze structure-activity relationships with good predictive power (r(2) = 0.921; q(2) = 0.582). Moreover, the CoMFA model showed that the length of the molecule, the amide, and the amine moieties all played crucial roles in anti-HIV activity. These results suggest that 7g may serve as a lead for the development of novel anti-HIV-1 therapies. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.05.070
• 作为产物：
  描述：

  methyl 4-((1H-benzo[d]imidazol-1-yl)methyl)benzoate 在 一水合肼 作用下， 反应 4.0h， 以79%的产率得到4-Benzoimidazol-1-ylmethyl-benzoic acid hydrazide
  参考文献：
  名称：

  Synthesis of 4-(1H-Azol-1-ylmethyl)benzohydrazides and Their Acyclic and Heterocyclic Derivatives

  摘要：

  4-(1H-吡唑-1-基甲基)苯并酰肼类化合物由甲基4-(溴甲基)苯甲酸酯、吡唑和肼水合物制备得到。4-(1H-咪唑-1-基甲基)苯并酰肼与羰基化合物反应生成脎，并研究了其互变异构现象。从这些酰肼出发，合成了1,3,4-噁二唑、1,2,4-三唑-5-硫酮和N-苯甲酰基-N′-烷基(芳基)磺酰基酰肼类化合物。

  DOI：

  10.1007/s11176-005-0180-7

文献信息

• Synthesis of 4-(1H-Azol-1-ylmethyl)benzohydrazides and Their Acyclic and Heterocyclic Derivatives
  作者：V. A. Osyanin、P. P. Purygin、Z. P. Belousova

  DOI：10.1007/s11176-005-0180-7

  日期：2005.1

  4-(1H-Azol-1-ylmethyl)benzohydrazides were prepared from methyl 4-(bromomethyl)benzoate, azoles, and hydrazine hydrate. Reactions of 4-(1H-imidazol-1-ylmethyl)benzohydrazide with carbonyl compounds gave hydrazones whose tautomerism was studied. From the hydrazides, 1,3,4-oxadiazoles, 1,2,4-triazole- 5-thione, and N-benzoyl-N′-alkyl(aryl)sulfonylhydrazines were synthesized.

  4-(1H-吡唑-1-基甲基)苯并酰肼类化合物由甲基4-(溴甲基)苯甲酸酯、吡唑和肼水合物制备得到。4-(1H-咪唑-1-基甲基)苯并酰肼与羰基化合物反应生成脎，并研究了其互变异构现象。从这些酰肼出发，合成了1,3,4-噁二唑、1,2,4-三唑-5-硫酮和N-苯甲酰基-N′-烷基(芳基)磺酰基酰肼类化合物。
• Tricyclononene carboxamide derivatives as novel anti-HIV-1 agents
  作者：Ming-xin Dong、Jian Zhang、Xu-qing Peng、Hong Lu、Liu-hong Yun、Shibo Jiang、Qiu-yun Dai

  DOI：10.1016/j.ejmech.2010.05.070

  日期：2010.9

  By modifying the chemical structure of anti-orthopoxvirus compound ST-246, we designed and synthesized a series of tricyclononene carboxamide derivatives and tested their anti-HIV-1 activity and cytotoxicity. We found that benzoimidazol-containing compound 7g was highly effective in inhibiting HIV-1 R5 infection with an IC50 value of 0.41 mu M and a selectivity index of 292, but it exhibited no significant inhibitory activity on HIV-1 reverse transcriptase, integrase and protease. CoMFA was used to analyze structure-activity relationships with good predictive power (r(2) = 0.921; q(2) = 0.582). Moreover, the CoMFA model showed that the length of the molecule, the amide, and the amine moieties all played crucial roles in anti-HIV activity. These results suggest that 7g may serve as a lead for the development of novel anti-HIV-1 therapies. (C) 2010 Elsevier Masson SAS. All rights reserved.