4-methoxy-2-methylquinoline-6-carboxylic acid n-octylamide | 137873-00-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 4-methoxy-2-methylquinoline-6-carboxylic acid n-octylamide
• 英文别名: 4-methoxy-2-methyl-N-octylquinoline-6-carboxamide
• CAS: 137873-00-8
• 化学式: C₂₀H₂₈N₂O₂
• 分子量: 328.455
• InChiKey: FIWJPHCBQFAEDY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  51.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-methoxy-2-methylquinoline-6-carboxylic acid n-octylamide 在 乙酸铵 作用下， 反应 3.0h， 以69%的产率得到4-amino-2-methylquinoline-6-carboxylic acid n-octylamide
  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
• 作为产物：
  描述：

  4-羟基-2-甲基-5-喹啉羧酸 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 3.0h， 生成 4-methoxy-2-methylquinoline-6-carboxylic acid n-octylamide
  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

• Substituted aminoquinolines as modulators of chemokine receptor activity
  申请人：Merck & Co., Inc.

  公开号：US05919776A1

  公开（公告）日：1999-07-06

  The present invention is directed to aminoquinolines of Formula I: ##STR1## (wherein R.sup.1, R.sup.2, R.sup.3, and R.sup.4 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.

  本发明涉及公式I的氨基喹啉：##STR1##（其中R.sup.1，R.sup.2，R.sup.3和R.sup.4在此定义），它们可用作趋化因子受体活性的调节剂。特别地，这些化合物可用作趋化因子受体CCR-1、CCR-2、CCR-2A、CCR-2B、CCR-3、CCR-4、CCR-5、CXCR-3和/或CXCR-4的调节剂。
• 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.