N-(2-Chloro-pyrimidin-4-yl)-N',N'-dimethyl-benzene-1,4-diamine | 191728-96-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-(2-Chloro-pyrimidin-4-yl)-N',N'-dimethyl-benzene-1,4-diamine
• 英文别名: 1-N-(2-chloropyrimidin-4-yl)-4-N,4-N-dimethylbenzene-1,4-diamine
• CAS: 191728-96-8
• 化学式: C₁₂H₁₃ClN₄
• 分子量: 248.715
• InChiKey: TYQAEXBKHFXNAL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  41
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(2-Chloro-pyrimidin-4-yl)-N',N'-dimethyl-benzene-1,4-diamine 在 N,N-二异丙基乙胺 作用下， 以 N-甲基吡咯烷酮 、 1,2-二氯乙烷 为溶剂， 生成 3-(2-chlorophenyl)-1-[4-(dimethylamino)phenyl]-1-[2-[[(2S)-1-methoxypropan-2-yl]amino]pyrimidin-4-yl]urea
  参考文献：
  名称：

  Development of N-2,4-pyrimidine-N-phenyl-N′-phenyl ureas as inhibitors of tumor necrosis factor alpha (TNF-α) synthesis. Part 1

  摘要：

  A new class of tumor necrosis factor alpha (TNF-alpha) synthesis inhibitors based on an N-2,4-pyrimidine-N-phenyl-N'-phenyl urea scaffold is described. Many of these compounds showed low-nanomolar activity against lipopolysaccharide stimulated TNF-alpha production. X-ray co-crystallization studies with mutated p38alpha showed that these trisubstituted ureas interact with the ATP-binding pocket in a pseudo-bicyclic conformation brought about by the presence of an intramolecular hydrogen bonding interaction.

  DOI：

  10.1016/j.bmcl.2006.03.095
• 作为产物：
  描述：

  2,4-二氯嘧啶 、 N,N-二甲基-对苯二胺 在 sodium carbonate 作用下， 以 乙醇 为溶剂， 生成 N-(2-Chloro-pyrimidin-4-yl)-N',N'-dimethyl-benzene-1,4-diamine
  参考文献：
  名称：

  Development of N-2,4-pyrimidine-N-phenyl-N′-phenyl ureas as inhibitors of tumor necrosis factor alpha (TNF-α) synthesis. Part 1

  摘要：

  A new class of tumor necrosis factor alpha (TNF-alpha) synthesis inhibitors based on an N-2,4-pyrimidine-N-phenyl-N'-phenyl urea scaffold is described. Many of these compounds showed low-nanomolar activity against lipopolysaccharide stimulated TNF-alpha production. X-ray co-crystallization studies with mutated p38alpha showed that these trisubstituted ureas interact with the ATP-binding pocket in a pseudo-bicyclic conformation brought about by the presence of an intramolecular hydrogen bonding interaction.

  DOI：

  10.1016/j.bmcl.2006.03.095

文献信息

• SUBSTITUTED 2-ANILINOPYRIMIDINES USEFUL AS PROTEIN KINASE INHIBITORS
  申请人：CELLTECH THERAPEUTICS LIMITED

  公开号：EP0862560B1

  公开（公告）日：2003-04-02
• US5958935A
  申请人：——

  公开号：US5958935A

  公开（公告）日：1999-09-28
• US6235746B1
  申请人：——

  公开号：US6235746B1

  公开（公告）日：2001-05-22
• Development of N-2,4-pyrimidine-N-phenyl-N′-phenyl ureas as inhibitors of tumor necrosis factor alpha (TNF-α) synthesis. Part 1
  作者：Todd A. Brugel、Jennifer A. Maier、Michael P. Clark、Mark Sabat、Adam Golebiowski、Roger G. Bookland、Matthew J. Laufersweiler、Steven K. Laughlin、John C. VanRens、Biswanath De、Lily C. Hsieh、Marlene J. Mekel、Michael J. Janusz

  DOI：10.1016/j.bmcl.2006.03.095

  日期：2006.7

  A new class of tumor necrosis factor alpha (TNF-alpha) synthesis inhibitors based on an N-2,4-pyrimidine-N-phenyl-N'-phenyl urea scaffold is described. Many of these compounds showed low-nanomolar activity against lipopolysaccharide stimulated TNF-alpha production. X-ray co-crystallization studies with mutated p38alpha showed that these trisubstituted ureas interact with the ATP-binding pocket in a pseudo-bicyclic conformation brought about by the presence of an intramolecular hydrogen bonding interaction.