N⁴-Cyclohexylmethyl-2-(4-methyl-piperazin-1-yl)-5-nitro-N¹-phenyl-benzene-1,4-diamine | 675103-17-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: N⁴-Cyclohexylmethyl-2-(4-methyl-piperazin-1-yl)-5-nitro-N¹-phenyl-benzene-1,4-diamine
• 英文别名: N4-cyclohexylmethyl-2-(4-methyl-piperazin-1-yl)-5-nitro-N1-phenyl-benzene-1,4-diamine；4-N-(cyclohexylmethyl)-2-(4-methylpiperazin-1-yl)-5-nitro-1-N-phenylbenzene-1,4-diamine
• CAS: 675103-17-0
• 化学式: C₂₄H₃₃N₅O₂
• 分子量: 423.558
• InChiKey: VMJALJMKISVGKM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  76.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N⁴-Cyclohexylmethyl-2-(4-methyl-piperazin-1-yl)-5-nitro-N¹-phenyl-benzene-1,4-diamine 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 16.0h， 以75%的产率得到N1-cyclohexylmethyl-5-(4-methyl-piperazin-1-yl)-N4-phenyl-benzene-1,2,4-triamine
  参考文献：
  名称：

  Discovery and design of benzimidazolone based inhibitors of p38 MAP kinase

  摘要：

  A new class of benzimidazolone p38 MAP kinase inhibitors was discovered through high-throughput screening. X-ray crystallographic data of the lead molecule with p38 were used to design analogues with improved binding affinity and potency in a cell assay of LPS-induced TNF alpha production. Herein, we report the SAR of this new class of p38 inhibitors. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.09.014
• 作为产物：
  描述：

  2,4-二氟-5-硝基苯胺 在 copper diacetate 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 86.0h， 生成 N⁴-Cyclohexylmethyl-2-(4-methyl-piperazin-1-yl)-5-nitro-N¹-phenyl-benzene-1,4-diamine
  参考文献：
  名称：

  Discovery and design of benzimidazolone based inhibitors of p38 MAP kinase

  摘要：

  A new class of benzimidazolone p38 MAP kinase inhibitors was discovered through high-throughput screening. X-ray crystallographic data of the lead molecule with p38 were used to design analogues with improved binding affinity and potency in a cell assay of LPS-induced TNF alpha production. Herein, we report the SAR of this new class of p38 inhibitors. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.09.014

文献信息

• Heterocyclic compounds
  申请人：Boehringer Ingelheim Parmaceuticals, Inc.

  公开号：US20040192748A1

  公开（公告）日：2004-09-30

  Disclosed are benzimidazolone compounds of formulas (I) & (II): 1 wherein R 1 , R 2 , R 3 , R 4 , R 5 , X, L, m, n and t are defined herein. The compounds inhibit production of cytokines involved in inflammatory processes and are thus useful for treating diseases and pathological conditions involving inflammation such as chronic inflammatory disease. Also disclosed are processes for preparing these compounds and pharmaceutical compositions comprising these compounds.

  本发明涉及化合物(I)和(II)，其化学式如下：其中，R1、R2、R3、R4、R5、X、L、m、n和t的定义如下。这些化合物抑制涉及炎症过程的细胞因子的产生，因此可用于治疗涉及炎症的疾病和病理条件，如慢性炎症性疾病。还公开了制备这些化合物的方法和包含这些化合物的制药组合物。
• BENZIMIDAZOLONES AND THEIR USE AS CYTOKINE INHIBITORS
  申请人：Boehringer Ingelheim Pharmaceuticals Inc.

  公开号：EP1539708B1

  公开（公告）日：2007-12-26
• Discovery and design of benzimidazolone based inhibitors of p38 MAP kinase
  作者：Abdelhakim Hammach、Antonio Barbosa、Faith Corbo Gaenzler、Tazmeen Fadra、Daniel Goldberg、Ming-Hong Hao、Rachel R. Kroe、Pingrong Liu、Kevin C. Qian、Mark Ralph、Christopher Sarko、Fariba Soleymanzadeh、Neil Moss

  DOI：10.1016/j.bmcl.2006.09.014

  日期：2006.12

  A new class of benzimidazolone p38 MAP kinase inhibitors was discovered through high-throughput screening. X-ray crystallographic data of the lead molecule with p38 were used to design analogues with improved binding affinity and potency in a cell assay of LPS-induced TNF alpha production. Herein, we report the SAR of this new class of p38 inhibitors. (c) 2006 Elsevier Ltd. All rights reserved.