N-methyl-2-(trifluoromethyl)-1H-benzimidazole-5-carboxamide | 1375485-67-8

• 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: N-methyl-2-(trifluoromethyl)-1H-benzimidazole-5-carboxamide
• 英文别名: N-methyl-2-(trifluoromethyl)-3H-benzimidazole-5-carboxamide
• CAS: 1375485-67-8
• 化学式: C₁₀H₈F₃N₃O
• 分子量: 243.188
• InChiKey: PFFHKMHNVFOBMB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  57.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3,4-二氨基苯甲酸 在 盐酸 、 氯化亚砜 作用下， 以 水 为溶剂， 反应 26.67h， 生成 N-methyl-2-(trifluoromethyl)-1H-benzimidazole-5-carboxamide
  参考文献：
  名称：

  Exploring the interplay of physicochemical properties, membrane permeability and giardicidal activity of some benzimidazole derivatives

  摘要：

  This study evaluated the relationship between the physicochemical properties, membrane permeability and in vitro giardicidal activity of twenty nine benzimidazole derivatives (1-7n). The retention time data from reverse phase high performance chromatography (RP-HPLC) were used to estimate aqueous solubility and lipophilicity of these compounds. The apparent permeability was determined using Caco-2 cell monolayer. The calculation of some descriptors, such as Clog P. PSA, was performed using ACD labs software. For benzimidazole derivatives with NHCOOCH3, CH3, NH2, SH and SCH3 groups at the 2-position, a quadratic type of regression model was obtained with giardicidal activity and aqueous solubility or lipophilicity. On the other hand, giardicidal activity of 2-(trifluoromethyl)-1H-benzimidazole derivatives was influenced by lipophilicity, hydrogen bond donors and molecular volume but it was not determined by their apparent permeability in Caco-2 cell line. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.03.014

文献信息

• Exploring the interplay of physicochemical properties, membrane permeability and giardicidal activity of some benzimidazole derivatives
  作者：Carlos Hernández-Covarrubias、Miguel A. Vilchis-Reyes、Lilian Yépez-Mulia、Remedios Sánchez-Díaz、Gabriel Navarrete-Vázquez、Alicia Hernández-Campos、Rafael Castillo、Francisco Hernández-Luis

  DOI：10.1016/j.ejmech.2012.03.014

  日期：2012.6

  This study evaluated the relationship between the physicochemical properties, membrane permeability and in vitro giardicidal activity of twenty nine benzimidazole derivatives (1-7n). The retention time data from reverse phase high performance chromatography (RP-HPLC) were used to estimate aqueous solubility and lipophilicity of these compounds. The apparent permeability was determined using Caco-2 cell monolayer. The calculation of some descriptors, such as Clog P. PSA, was performed using ACD labs software. For benzimidazole derivatives with NHCOOCH3, CH3, NH2, SH and SCH3 groups at the 2-position, a quadratic type of regression model was obtained with giardicidal activity and aqueous solubility or lipophilicity. On the other hand, giardicidal activity of 2-(trifluoromethyl)-1H-benzimidazole derivatives was influenced by lipophilicity, hydrogen bond donors and molecular volume but it was not determined by their apparent permeability in Caco-2 cell line. (C) 2012 Elsevier Masson SAS. All rights reserved.