2-[4-(2-Trifluoromethylbenzoyl)phenyl]-1H-benzimidazole-5-carboxylic acid | 1123819-61-3

• 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: 2-[4-(2-Trifluoromethylbenzoyl)phenyl]-1H-benzimidazole-5-carboxylic acid
• 英文别名: 2-[4-[2-(trifluoromethyl)benzoyl]phenyl]-3H-benzimidazole-5-carboxylic acid
• CAS: 1123819-61-3
• 化学式: C₂₂H₁₃F₃N₂O₃
• 分子量: 410.352
• InChiKey: BECFDTCNWBOUDF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  83
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-氨基甲基噻唑 、 2-[4-(2-Trifluoromethylbenzoyl)phenyl]-1H-benzimidazole-5-carboxylic acid 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 N-(1,3-thiazol-2-ylmethyl)-2-[4-[2-(trifluoromethyl)benzoyl]phenyl]-3H-benzimidazole-5-carboxamide
  参考文献：
  名称：

  Benzimidazole-carboxamides as potent and bioavailable stearoyl-CoA desaturase (SCD1) inhibitors from ligand-based virtual screening and chemical optimization

  摘要：

  The discovery of potent benzimidazole stearoyl-CoA desaturase (SCD1) inhibitors by ligand-based virtual screening is described. ROCS 3D-searching gave a favorable chemical motif that was subsequently optimized to arrive at a chemical series of potent and promising SCD1 inhibitors. In particular, compound SAR224 was selected for further pharmacological profiling based on favorable in vitro data. After oral administration to male ZDF rats, this compound significantly decreased the serum fatty acid desaturation index, thus providing conclusive evidence for SCD1 inhibition in vivo by SAR224. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.01.030
• 作为产物：
  描述：

  (4-[1,3]dioxan-2-ylphenyl)-(2-trifluoromethylphenyl)methanone 在 sodium metabisulfite 、 水 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 生成 2-[4-(2-Trifluoromethylbenzoyl)phenyl]-1H-benzimidazole-5-carboxylic acid
  参考文献：
  名称：

  Benzimidazole-carboxamides as potent and bioavailable stearoyl-CoA desaturase (SCD1) inhibitors from ligand-based virtual screening and chemical optimization

  摘要：

  The discovery of potent benzimidazole stearoyl-CoA desaturase (SCD1) inhibitors by ligand-based virtual screening is described. ROCS 3D-searching gave a favorable chemical motif that was subsequently optimized to arrive at a chemical series of potent and promising SCD1 inhibitors. In particular, compound SAR224 was selected for further pharmacological profiling based on favorable in vitro data. After oral administration to male ZDF rats, this compound significantly decreased the serum fatty acid desaturation index, thus providing conclusive evidence for SCD1 inhibition in vivo by SAR224. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.01.030
• 作为试剂：
  描述：

  3,4-二氨基苯甲酸 、 、 4-(2-trifluoromethylbenzoyl)benzaldehyde 在 二氯甲烷 、 2-[4-(2-Trifluoromethylbenzoyl)phenyl]-1H-benzimidazole-5-carboxylic acid 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以resulted in 3.49 g of 2-[4-(2-trifluoromethylbenzoyl)phenyl]-1H-benzimidazole-5-carboxylic acid的产率得到2-[4-(2-Trifluoromethylbenzoyl)phenyl]-1H-benzimidazole-5-carboxylic acid
  参考文献：
  名称：

  AZOLOARINE DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF, PHARMACEUTICALS CONTAINING THESE COMPOUNDS AND THE USE THEREOF

  摘要：

  本发明涉及式I的氮杂芘衍生物，其中R、A、B、D、Y、X、M和W如本文所定义，并且其生理上可耐受的盐。

  公开号：

  US20100240580A1

文献信息

• AZOLOARIN DERIVATE, VERFAHREN ZU DEREN HERSTELLUNG, DIESE VERBINDUNGEN ENTHALTENDE ARZNEIMITTEL UND DEREN VERWENDUNG
  申请人：Sanofi-Aventis

  公开号：EP2183222A2

  公开（公告）日：2010-05-12
• [DE] AZOLOARIN DERIVATE, VERFAHREN ZU DEREN HERSTELLUNG, DIESE VERBINDUNGEN ENTHALTENDE ARZNEIMITTEL UND DEREN VERWENDUNG<br/>[EN] AZOLORAINE DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF, PHARMACEUTICALS CONTAINING THESE COMPOUNDS, AND THE USE THEREOF<br/>[FR] DÉRIVÉS D'AZOLOARINE, LEURS PROCÉDÉS DE PRODUCTION, PRODUITS PHARMACEUTIQUES CONTENANT CES COMPOSÉS ET UTILISATIONS DE CES PRODUITS
  申请人：SANOFI AVENTIS

  公开号：WO2009024287A2

  公开（公告）日：2009-02-26

  Die Erfindung betrifft Verbindungen der Formel (I) worin die Reste R, M, W, X, A, B, D und Y die angegebenen Bedeutungen haben, sowie deren physiologisch verträgliche Salze. Die Verbindungen eignen sich z.B. zur Behandlung des metabolischen Syndrom, Insulinresistenz, Obesitas und Diabetes.
• Benzimidazole-carboxamides as potent and bioavailable stearoyl-CoA desaturase (SCD1) inhibitors from ligand-based virtual screening and chemical optimization
  作者：Hans Matter、Gerhard Zoller、Andreas W. Herling、Juan-Antonio Sanchez-Arias、Christophe Philippo、Claudie Namane、Markus Kohlmann、Anja Pfenninger、Marc D. Voss

  DOI：10.1016/j.bmcl.2013.01.030

  日期：2013.3

  The discovery of potent benzimidazole stearoyl-CoA desaturase (SCD1) inhibitors by ligand-based virtual screening is described. ROCS 3D-searching gave a favorable chemical motif that was subsequently optimized to arrive at a chemical series of potent and promising SCD1 inhibitors. In particular, compound SAR224 was selected for further pharmacological profiling based on favorable in vitro data. After oral administration to male ZDF rats, this compound significantly decreased the serum fatty acid desaturation index, thus providing conclusive evidence for SCD1 inhibition in vivo by SAR224. (C) 2013 Elsevier Ltd. All rights reserved.
• AZOLOARINE DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF, PHARMACEUTICALS CONTAINING THESE COMPOUNDS AND THE USE THEREOF
  申请人：ZOLLER Gerhard

  公开号：US20100240580A1

  公开（公告）日：2010-09-23

  The invention relates to azoloarine derivatives of formula I wherein R, A, B, D, Y, X, M and W are as defined herein, and their physiologically tolerated salts.

  本发明涉及公式I的氮杂芴衍生物，其中R，A，B，D，Y，X，M和W的定义如本文所述，并且其生理上耐受的盐。