N-butyl-2-chloro-5-nitropyrimidin-4-amine | 890094-46-9

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: N-butyl-2-chloro-5-nitropyrimidin-4-amine
• CAS: 890094-46-9
• 化学式: C₈H₁₁ClN₄O₂
• 分子量: 230.654
• InChiKey: VYIGIGYPIKKRBS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  83.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-butyl-2-chloro-5-nitropyrimidin-4-amine 在 palladium on activated charcoal 氢气 、 N,N-二异丙基乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 3.75h， 生成 9-butyl-N-8-(2-chloro-phenyl)-N-2-(2,6-difluoro-phenyl)-9H-purine-2,8-diamine
  参考文献：
  名称：

  The development of novel C-2, C-8, and N-9 trisubstituted purines as inhibitors of TNF-α production

  摘要：

  A series of C-2, C-8, and N-9 trisubstituted purine based inhibitors of TNF-alpha production are described. The most potent analogs showed low nanomolar activity against LPS-induced TNF-alpha production in a THP-1 cell based assay. The SAR of the series was optimized with the aid of X-ray co-crystal structures of these inhibitors bound with mutated p38 (mp38).

  DOI：

  10.1016/j.bmcl.2006.05.050
• 作为产物：
  描述：

  正丁胺 、 2,4-二氯-5 硝基嘧啶 以 四氢呋喃 为溶剂， 反应 0.17h， 生成 N-butyl-2-chloro-5-nitropyrimidin-4-amine
  参考文献：
  名称：

  The development of novel C-2, C-8, and N-9 trisubstituted purines as inhibitors of TNF-α production

  摘要：

  A series of C-2, C-8, and N-9 trisubstituted purine based inhibitors of TNF-alpha production are described. The most potent analogs showed low nanomolar activity against LPS-induced TNF-alpha production in a THP-1 cell based assay. The SAR of the series was optimized with the aid of X-ray co-crystal structures of these inhibitors bound with mutated p38 (mp38).

  DOI：

  10.1016/j.bmcl.2006.05.050

文献信息

• PURINES AS PKC-THETA INHIBITORS
  申请人：Neagu Irina

  公开号：US20110046131A1

  公开（公告）日：2011-02-24

  A chemical genus of purines, which are useful as PKCθ inhibitors, is disclosed. The genus is represented by the formula (I); A representative example is: (II)

  揭示了一种嘌呤的化学属，其作为PKCθ抑制剂具有用处。该属由公式（I）表示；代表性例子为：（II）。
• The development of novel C-2, C-8, and N-9 trisubstituted purines as inhibitors of TNF-α production
  作者：Mark Sabat、John C. VanRens、Michael P. Clark、Todd A. Brugel、Jennifer Maier、Roger G. Bookland、Matthew J. Laufersweiler、Steven K. Laughlin、Adam Golebiowski、Biswanath De、Lily C. Hsieh、Richard L. Walter、Marlene J. Mekel、Michael J. Janusz

  DOI：10.1016/j.bmcl.2006.05.050

  日期：2006.8

  A series of C-2, C-8, and N-9 trisubstituted purine based inhibitors of TNF-alpha production are described. The most potent analogs showed low nanomolar activity against LPS-induced TNF-alpha production in a THP-1 cell based assay. The SAR of the series was optimized with the aid of X-ray co-crystal structures of these inhibitors bound with mutated p38 (mp38).