1-(4,4'-dipropylbenzhydryl)benzimidazole-6-carboxylic acid | 156674-27-0

• 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: 1-(4,4'-dipropylbenzhydryl)benzimidazole-6-carboxylic acid
• 英文别名: 3-[Bis(4-propylphenyl)methyl]benzimidazole-5-carboxylic acid
• CAS: 156674-27-0
• 化学式: C₂₇H₂₈N₂O₂
• 分子量: 412.532
• InChiKey: GNCMQQNQTVZNCD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  55.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(4,4'-dipropylbenzhydryl)benzimidazole-6-carboxylic acid 在 sodium hydroxide 、 三正丁胺 、 2-氯-1-甲基吡啶碘化物 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 4.0h， 生成
  参考文献：
  名称：

  Indole and benzimidazole derivatives as steroid 5α-reductase inhibitors in the rat prostate

  摘要：

  A novel series of indole and benzimidazole derivatives were synthesized and evaluated for their inhibitory activity of rat prostatic 5 alpha-reductase. Among these compounds, 4-{2-[1-(4,4'-dipropylbenzhydryl)indole-5-carboxamido]phenoxy)butyric acid (15) and its benzimidazole analogue 25 showed potent inhibitory activities for rat prostatic 5 alpha-reductase (IC50 values of 9.6+/-1.0 and 13+/-1.5 nM, respectively), with the potency very close to that of finasteride. Compound 30, in which the moiety between the benzene ring and amide bond was replaced by quinolin-4-one ring, showed almost equipotent activity (IC50=19+/-6.2 nM) with the correspondent amide derivative 13. This result was consistent with the previous observation that the coplanarity of this moiety might contribute to the potent inhibitory activity. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(98)80018-7
• 作为产物：
  描述：

  1H-苯并咪唑-5-羧酸 、 4,4'-dipropylbenzhydryl bromide 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 3.0h， 以39%的产率得到1-(4,4'-dipropylbenzhydryl)benzimidazole-6-carboxylic acid
  参考文献：
  名称：

  Indole and benzimidazole derivatives as steroid 5α-reductase inhibitors in the rat prostate

  摘要：

  A novel series of indole and benzimidazole derivatives were synthesized and evaluated for their inhibitory activity of rat prostatic 5 alpha-reductase. Among these compounds, 4-{2-[1-(4,4'-dipropylbenzhydryl)indole-5-carboxamido]phenoxy)butyric acid (15) and its benzimidazole analogue 25 showed potent inhibitory activities for rat prostatic 5 alpha-reductase (IC50 values of 9.6+/-1.0 and 13+/-1.5 nM, respectively), with the potency very close to that of finasteride. Compound 30, in which the moiety between the benzene ring and amide bond was replaced by quinolin-4-one ring, showed almost equipotent activity (IC50=19+/-6.2 nM) with the correspondent amide derivative 13. This result was consistent with the previous observation that the coplanarity of this moiety might contribute to the potent inhibitory activity. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(98)80018-7