4-amino-N-cyclohexyl-N-methyl-3-nitrobenzamide | 53050-31-0

• 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: 4-amino-N-cyclohexyl-N-methyl-3-nitrobenzamide
• CAS: 53050-31-0
• 化学式: C₁₄H₁₉N₃O₃
• 分子量: 277.323
• InChiKey: KCLQFLUBXKISGZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  92.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-amino-N-cyclohexyl-N-methyl-3-nitrobenzamide 在 palladium on activated charcoal 甲酸铵 作用下， 以 乙醇 为溶剂， 生成 3,4-diamino-N-cyclohexyl-N-methylbenzamide
  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：

  N-cyclohexyl-4-fluoro-N-methyl-3-nitrobenzamide 在 氨 、 三乙胺 作用下， 以 二甲基亚砜 为溶剂， 生成 4-amino-N-cyclohexyl-N-methyl-3-nitrobenzamide
  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

• US4015934A
  申请人：——

  公开号：US4015934A

  公开（公告）日：1977-04-05
• 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.