N-[2-amino-1-(3-methoxypropyl)-1H-benzimidazol-5-yl]-N-methylcyclohexanecarboxamide

• 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: N-[2-amino-1-(3-methoxypropyl)-1H-benzimidazol-5-yl]-N-methylcyclohexanecarboxamide
• 英文别名: N-[2-amino-1-(3-methoxypropyl)benzimidazol-5-yl]-N-methylcyclohexanecarboxamide
• 化学式: C₁₉H₂₈N₄O₂
• 分子量: 344.457
• InChiKey: LNUKMPLWSPWJNX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  73.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  对氰基苯甲酸 、 N-[2-amino-1-(3-methoxypropyl)-1H-benzimidazol-5-yl]-N-methylcyclohexanecarboxamide 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 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 24.0h， 生成 4-cyano-N-(1-(3-methoxypropyl)-5-(N-methylcyclohexanecarboxamido)-1H-benzo[d]imidazol-2-yl)benzamide
  参考文献：
  名称：

  Discovery, SAR and X-ray structure of 1H-benzimidazole-5-carboxylic acid cyclohexyl-methyl-amides as inhibitors of inducible T-cell kinase (Itk)

  摘要：

  A series of novel potent benzimidazole based inhibitors of interleukin-2 T-cell kinase (Itk) were prepared. In this report, we discuss the structure-activity relationship (SAR), selectivity, and cell-based activity for the series. We also discuss the SAR associated with an X-ray structure of one of the small-molecule inhibitors bound to ITK. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.09.015
• 作为产物：
  描述：

  溴化氰 、 N-[3-amino-4-(3-methoxypropylamino)phenyl]-N-methylcyclohexanecarboxamide 以 乙醇 为溶剂， 反应 24.0h， 生成 N-[2-amino-1-(3-methoxypropyl)-1H-benzimidazol-5-yl]-N-methylcyclohexanecarboxamide
  参考文献：
  名称：

  Discovery, SAR and X-ray structure of 1H-benzimidazole-5-carboxylic acid cyclohexyl-methyl-amides as inhibitors of inducible T-cell kinase (Itk)

  摘要：

  A series of novel potent benzimidazole based inhibitors of interleukin-2 T-cell kinase (Itk) were prepared. In this report, we discuss the structure-activity relationship (SAR), selectivity, and cell-based activity for the series. We also discuss the SAR associated with an X-ray structure of one of the small-molecule inhibitors bound to ITK. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.09.015

文献信息

• [EN] NOVEL UREA DERIVATIVES AS TEC KINASE INHIBITORS AND USES THEREOF<br/>[FR] NOUVEAUX DÉRIVÉS D'URÉE EN TANT QU'INHIBITEURS DE KINASE TEC ET LEURS UTILISATIONS
  申请人：GLENMARK PHARMACEUTICALS SA

  公开号：WO2013024427A1

  公开（公告）日：2013-02-21

  Provided are urea compounds of formula (I) as Tec kinase inhibitors, in particular ITK (interleukin-2 inducible tyrosine kinase) inhibitors. Also provided herein are processes for preparing compounds described herein, intermediates used in their synthesis, pharmaceutical compositions thereof, and methods for treating or preventing diseases, conditions and/or disorders mediated by ITK.

  提供的是式（I）的尿素化合物，作为Tec激酶抑制剂，特别是ITK（白细胞介素-2诱导酪氨酸激酶）抑制剂。本文还提供了制备所述化合物的方法、用于合成的中间体、药物组合物以及治疗或预防由ITK介导的疾病、状况和/或紊乱的方法。
• Discovery, SAR and X-ray structure of 1H-benzimidazole-5-carboxylic acid cyclohexyl-methyl-amides as inhibitors of inducible T-cell kinase (Itk)
  作者：Kevin J. Moriarty、Hidenori Takahashi、Steven S. Pullen、Hnin Hnin Khine、Rosemarie H. Sallati、Ernest L. Raymond、Joseph R. Woska、Deborah D. Jeanfavre、Gregory P. Roth、Michael P. Winters、Lei Qiao、Declan Ryan、Renee DesJarlais、Darius Robinson、Matthew Wilson、Mark Bobko、Brian N. Cook、Ho Yin Lo、Peter A. Nemoto、Mohammed A. Kashem、John P. Wolak、André White、Ronald L. Magolda、Bruce Tomczuk

  DOI：10.1016/j.bmcl.2008.09.015

  日期：2008.10

  A series of novel potent benzimidazole based inhibitors of interleukin-2 T-cell kinase (Itk) were prepared. In this report, we discuss the structure-activity relationship (SAR), selectivity, and cell-based activity for the series. We also discuss the SAR associated with an X-ray structure of one of the small-molecule inhibitors bound to ITK. (c) 2008 Elsevier Ltd. All rights reserved.