N-cyclohexyl-4-(3-hydroxy-propylamino)-N-methyl-3-nitro-benzamide | 529505-90-6

• 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: N-cyclohexyl-4-(3-hydroxy-propylamino)-N-methyl-3-nitro-benzamide
• 英文别名: N-cyclohexyl-4-(3-hydroxypropylamino)-N-methyl-3-nitrobenzamide
• CAS: 529505-90-6
• 化学式: C₁₇H₂₅N₃O₄
• 分子量: 335.403
• InChiKey: SFDRODAQEXCALW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  98.4
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-cyclohexyl-4-(3-hydroxy-propylamino)-N-methyl-3-nitro-benzamide 在 palladium on activated charcoal 甲酸铵 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成 2-amino-1-(3-hydroxypropyl)-1H-benzimidazole-5-carboxylic acid N-cyclohexyl-N-methyl-amide
  参考文献：
  名称：

  Hit-to-lead studies on benzimidazole inhibitors of ITK: Discovery of a novel class of kinase inhibitors

  摘要：

  Benzimidazole 1 was identified as a selective inhibitor of ITK by high throughput screening. Hit-to-lead studies defined the SAR at all three substituents. Reversing the amide linkage at C6 led to 16, with a fivefold improvement of potency. This enhancement is rationalized by the conformational preference of the substituent. A model for the binding of the benzimidazoles to the ATP-binding site of ITK is proposed. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.04.045
• 作为产物：
  描述：

  4-氟-3-硝基苯甲酸 在 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 生成 N-cyclohexyl-4-(3-hydroxy-propylamino)-N-methyl-3-nitro-benzamide
  参考文献：
  名称：

  Hit-to-lead studies on benzimidazole inhibitors of ITK: Discovery of a novel class of kinase inhibitors

  摘要：

  Benzimidazole 1 was identified as a selective inhibitor of ITK by high throughput screening. Hit-to-lead studies defined the SAR at all three substituents. Reversing the amide linkage at C6 led to 16, with a fivefold improvement of potency. This enhancement is rationalized by the conformational preference of the substituent. A model for the binding of the benzimidazoles to the ATP-binding site of ITK is proposed. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.04.045

文献信息

• Substituted benzimidazole compounds
  申请人：Boehringer Ingelheim Pharmaceuticals, Inc.

  公开号：US20030144281A1

  公开（公告）日：2003-07-31

  Disclosed are substituted benzimidazole compounds of formula(I): 1 wherein R 1 , R 2 , R 3 , R 4 and X a are defined herein. The compounds of the invention are useful for treating diseases and pathological conditions involving inflammation, immunological disorders and allergic disorders. Also disclosed are processes for preparing these compounds and to pharmaceutical compositions comprising these compounds.

  揭示了一种公式（I）的取代苯并咪唑化合物：其中R1、R2、R3、R4和Xa在此处定义。该发明的化合物可用于治疗涉及炎症、免疫紊乱和过敏性疾病的疾病和病理状况。还揭示了制备这些化合物的方法以及包含这些化合物的药物组合物。
• US6825219B2
  申请人：——

  公开号：US6825219B2

  公开（公告）日：2004-11-30
• Hit-to-lead studies on benzimidazole inhibitors of ITK: Discovery of a novel class of kinase inhibitors
  作者：Roger J. Snow、Asitha Abeywardane、Scot Campbell、John Lord、Mohammed A. Kashem、Hnin Hnin Khine、Josephine King、Jennifer A. Kowalski、Steven S. Pullen、Teresa Roma、Gregory P. Roth、Christopher R. Sarko、Noel S. Wilson、Michael P. Winters、John P. Wolak、Charles L. Cywin

  DOI：10.1016/j.bmcl.2007.04.045

  日期：2007.7

  Benzimidazole 1 was identified as a selective inhibitor of ITK by high throughput screening. Hit-to-lead studies defined the SAR at all three substituents. Reversing the amide linkage at C6 led to 16, with a fivefold improvement of potency. This enhancement is rationalized by the conformational preference of the substituent. A model for the binding of the benzimidazoles to the ATP-binding site of ITK is proposed. (c) 2007 Elsevier Ltd. All rights reserved.