4-Amino-6-(3'-trifluoromethyl-trans-cinnamoyl)amino-2-methyl-quinoline | 137872-87-8

• 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-Amino-6-(3'-trifluoromethyl-trans-cinnamoyl)amino-2-methyl-quinoline
• 英文别名: (E)-N-(4-Amino-2-methyl-6-quinolinyl)-3-trifluoromethylcinnamamide；(E)-N-(4-amino-2-methylquinolin-6-yl)-3-[3-(trifluoromethyl)phenyl]prop-2-enamide
• CAS: 137872-87-8
• 化学式: C₂₀H₁₆F₃N₃O
• 分子量: 371.362
• InChiKey: CQPFKMRAYQKWEI-VMPITWQZSA-N

物化性质

• 沸点：
  594.8±50.0 °C(Predicted)
• 密度：
  1.371±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  68
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  N-(4-methoxy-2-methyl-6-quinolyl)acetamide 在 盐酸 、 溶剂黄146 作用下， 反应 1.0h， 生成 4-Amino-6-(3'-trifluoromethyl-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
• [EN] SUBSTITUTED AMINOQUINOLINES AS MODULATORS OF CHEMOKINE RECEPTOR ACTIVITY<br/>[FR] AMINOQUINOLEINES SUBSTITUEES UTILISEES COMME MODULATEURS DE L'ACTIVITE DES RECEPTEURS DE LA CHEMOKINE
  申请人：MERCK & CO., INC.

  公开号：WO1998027815A1

  公开（公告）日：1998-07-02

  (EN) The present invention is directed to aminoquinolines of formula (I), (wherein R1, R2, R3 and R4 are defined herein) which are useful as modulators of chemokine receptor activity. In particular, these compounds are useful as modulators of the chemokine receptors CCR-1, CCR-2, CCR-2A, CCR-2B, CCR-3, CCR-4, CCR-5, CXCR-3 and/or CXCR-4.(FR) L'invention concerne des aminoquinoléines de formule (I) (dans laquelle R1, R2, R3 et R4 sont définis dans la description), utiles en tant que modulateurs de l'activité des récepteurs de la chémokine. Ces composés sont notamment utiles en tant que modulateurs des récepteurs de la chémokine CCR-1, CCR-2, CCR-2A, CCR-2B, CCR-3, CCR-4, CCR-5, CXCR-3 et/ou CXCR-4.
• 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.