Ethyl 4-[2-[[1-[bis(4-propylphenyl)methyl]benzimidazole-5-carbonyl]amino]phenoxy]butanoate | 220644-71-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Ethyl 4-[2-[[1-[bis(4-propylphenyl)methyl]benzimidazole-5-carbonyl]amino]phenoxy]butanoate
• CAS: 220644-71-3
• 化学式: C₃₉H₄₃N₃O₄
• 分子量: 617.788
• InChiKey: YXJJLBAJZIROOJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.8
• 重原子数：
  46
• 可旋转键数：
  16
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  82.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Ethyl 4-[2-[[1-[bis(4-propylphenyl)methyl]benzimidazole-5-carbonyl]amino]phenoxy]butanoate 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 3.0h， 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 在 三正丁胺 、 potassium tert-butylate 、 2-氯-1-甲基吡啶碘化物 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 Ethyl 4-[2-[[1-[bis(4-propylphenyl)methyl]benzimidazole-5-carbonyl]amino]phenoxy]butanoate
  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

文献信息

• Indole and benzimidazole derivatives as steroid 5α-reductase inhibitors in the rat prostate
  作者：Hitoshi Takami、Nobuyuki Kishibayashi、Akio Ishii、Toshiaki Kumazawa

  DOI：10.1016/s0968-0896(98)80018-7

  日期：1998.12

  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.