4-n-Octylamino-6-(2'-chloro-trans-cinnamoyl)amino-2-methyl-quinoline | 137872-94-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 4-n-Octylamino-6-(2'-chloro-trans-cinnamoyl)amino-2-methyl-quinoline
• 英文别名: (E)-3-(2-chlorophenyl)-N-[2-methyl-4-(octylamino)quinolin-6-yl]prop-2-enamide
• CAS: 137872-94-7
• 化学式: C₂₇H₃₂ClN₃O
• 分子量: 450.024
• InChiKey: CWQLRNHZQNXHEL-DTQAZKPQSA-N

物化性质

• 沸点：
  653.4±55.0 °C(Predicted)
• 密度：
  1.178±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  32
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  54
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  辛胺盐酸盐 在 盐酸 、 溶剂黄146 作用下， 以 正丁醇 为溶剂， 反应 102.0h， 生成 4-n-Octylamino-6-(2'-chloro-trans-cinnamoyl)amino-2-methyl-quinoline
  参考文献：
  名称：

  Substituted 4,6-diaminoquinolines as inhibitors of C5a receptor binding

  摘要：

  The anaphylatoxin C5a is implicated in a number of inflammatory diseases. It is a highly cationic protein with 13 of 74 amino acids being either arginine or lysine. A search focusing on positively charged molecules, particularly amine-containing functionalities, led to the discovery of substituted 4,6-diaminoquinolines 1 [N,N'-bis(4-amino-2-methyl-6-quinolyl)urea] and 7 [6-N-(2-chlorocinnamoyl)-4,6-diamino-2-methylquinoline) as inhibitors of C5a receptor binding. These two compounds inhibited the binding of radiolabeled C5a to its receptor isolated from human neutrophils with IC50's = 3.3 and 12-mu-g/mL, respectively. Our efforts to enhance their potencies by chemical modification revealed a narrow profile of potency for effective C5a receptor binding inhibition.

  DOI：

  10.1021/jm00080a008

文献信息

• US5919776A
  申请人：——

  公开号：US5919776A

  公开（公告）日：1999-07-06
• Substituted 4,6-diaminoquinolines as inhibitors of C5a receptor binding
  作者：Thomas J. Lanza、Philippe L. Durette、Thomas Rollins、Salvatore Siciliano、Dana N. Cianciarulo、Sumire V. Kobayashi、Charles G. Caldwell、Martin S. Springer、William K. Hagmann

  DOI：10.1021/jm00080a008

  日期：1992.1

  The anaphylatoxin C5a is implicated in a number of inflammatory diseases. It is a highly cationic protein with 13 of 74 amino acids being either arginine or lysine. A search focusing on positively charged molecules, particularly amine-containing functionalities, led to the discovery of substituted 4,6-diaminoquinolines 1 [N,N'-bis(4-amino-2-methyl-6-quinolyl)urea] and 7 [6-N-(2-chlorocinnamoyl)-4,6-diamino-2-methylquinoline) as inhibitors of C5a receptor binding. These two compounds inhibited the binding of radiolabeled C5a to its receptor isolated from human neutrophils with IC50's = 3.3 and 12-mu-g/mL, respectively. Our efforts to enhance their potencies by chemical modification revealed a narrow profile of potency for effective C5a receptor binding inhibition.