[2-(2-chloro-6-fluoro-benzyl)-1-phenyl-1H-indol-3-yl]-piperazin-1-yl-methanone | 1174926-88-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: [2-(2-chloro-6-fluoro-benzyl)-1-phenyl-1H-indol-3-yl]-piperazin-1-yl-methanone
• 英文别名: (2-(2-chloro-6-fluorobenzyl)-1-phenyl-1H-indol-3-yl)(piperazin-1-yl)methanone；[2-[(2-chloro-6-fluorophenyl)methyl]-1-phenylindol-3-yl]-piperazin-1-ylmethanone
• CAS: 1174926-88-5
• 化学式: C₂₆H₂₃ClFN₃O
• 分子量: 447.94
• InChiKey: FCHVEQKBKCYQNN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  32
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-[2-(2-chloro-6-fluoro-benzyl)-1-phenyl-1H-indole-3-carbonyl]-piperazine-1-carboxylic acid tert-butyl ester 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 [2-(2-chloro-6-fluoro-benzyl)-1-phenyl-1H-indol-3-yl]-piperazin-1-yl-methanone
  参考文献：
  名称：

  Discovery and optimization of a new class of potent and non-chiral indole-3-carboxamide-based renin inhibitors

  摘要：

  Selective inhibition of the aspartyl protease renin has gained attraction as an interesting approach to control hypertension and associated cardiovascular risk factors given its unique position in the renin-angiotensin system. Using a combination of high-throughput screening, parallel synthesis, X-ray crystallography and structure-based design, we identified and optimized a novel series of potent and non-chiral indole-3-carboxamides with remarkable potency for renin. The most potent compound 5k displays an IC(50) value of 2 nM. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.08.092

文献信息

• CYCLIC INDOLE-3-CARBOXAMIDES, THEIR PREPARATION AND THEIR USE AS PHARMACEUTICALS
  申请人：STEINHAGEN Henning

  公开号：US20110039830A1

  公开（公告）日：2011-02-17

  The present invention relates to cyclic indole-3-carboxamides of the formula I, wherein A, R, R 10 , R 20 , R 30 , R 40 , n, p and q have the meanings indicated in the claims, which are valuable pharmaceutical active compounds. Specifically, they inhibit the enzyme renin and modulate the activity of the renin-angiotensin system, and are useful for the treatment of diseases such as hypertension, for example. The invention furthermore relates to processes for the preparation of the compounds of the formula I, their use and pharmaceutical compositions comprising them.

  本发明涉及公式I的环状吲哚-3-羧酰胺，其中A、R、R10、R20、R30、R40、n、p和q在权利要求书中所示，它们是有价值的药物活性化合物。具体而言，它们抑制酶肾素并调节肾素-血管紧张素系统的活性，可用于治疗高血压等疾病。本发明还涉及公式I化合物的制备方法、它们的使用以及包含它们的药物组合物。
• US8211885B2
  申请人：——

  公开号：US8211885B2

  公开（公告）日：2012-07-03
• [EN] CYCLIC INDOLE-3-CARBOXAMIDES, THEIR PREPARATION AND THEIR USE AS PHARMACEUTICALS<br/>[FR] INDOLE-3-CARBOXAMIDES CYCLIQUES, LEUR PRÉPARATION ET LEUR UTILISATION COMME PRODUITS PHARMACEUTIQUES
  申请人：SANOFI AVENTIS

  公开号：WO2009095163A2

  公开（公告）日：2009-08-06

  The present invention relates to cyclic indole-3-carboxamides of the Formula (I), wherein A, R, R10, R20, R30, R40, n, p and q have the meanings indicated in the claims, which are valuable pharmaceutical active compounds. Specifically, they inhibit the enzyme renin and modulate the activity of the renin-angiotensin system, and are useful for the treatment of diseases such as hypertension, for example. The invention furthermore relates to processes for the preparation of the compounds of the Formula (I), their use and pharmaceutical compositions comprising them.
• Discovery and optimization of a new class of potent and non-chiral indole-3-carboxamide-based renin inhibitors
  作者：Bodo Scheiper、Hans Matter、Henning Steinhagen、Ulrich Stilz、Zsolt Böcskei、Valérie Fleury、Gary McCort

  DOI：10.1016/j.bmcl.2010.08.092

  日期：2010.11

  Selective inhibition of the aspartyl protease renin has gained attraction as an interesting approach to control hypertension and associated cardiovascular risk factors given its unique position in the renin-angiotensin system. Using a combination of high-throughput screening, parallel synthesis, X-ray crystallography and structure-based design, we identified and optimized a novel series of potent and non-chiral indole-3-carboxamides with remarkable potency for renin. The most potent compound 5k displays an IC(50) value of 2 nM. (C) 2010 Elsevier Ltd. All rights reserved.