N-[(2R)-hexan-2-yl]-8-(methanesulfonamido)-4-oxo-1H-quinoline-2-carboxamide | 1424728-10-8

• 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: N-[(2R)-hexan-2-yl]-8-(methanesulfonamido)-4-oxo-1H-quinoline-2-carboxamide
• CAS: 1424728-10-8
• 化学式: C₁₇H₂₃N₃O₄S
• 分子量: 365.453
• InChiKey: UQQBSWNPGFGQRN-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  113
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  8-amino-1,4-dihydro-4-oxo-2-quinolinecarboxylic acid methyl ester 在 吡啶 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 sodium hydroxide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 34.5h， 生成 N-[(2R)-hexan-2-yl]-8-(methanesulfonamido)-4-oxo-1H-quinoline-2-carboxamide
  参考文献：
  名称：

  Amides of 4-hydroxy-8-methanesulfonylamino-quinoline-2-carboxylic acid as zinc-dependent inhibitors of Lp-PLA2

  摘要：

  AX10479, the phenyl amide of 4-hydroxy-8-methanesulfonylamino-quinoline-2-carboxylic acid, was identified as a Zn2+-dependent, 27 nM inhibitor of human plasma Lp-PLA(2). Structure-activity relationship studies focused on the AX10479 2-phenylamide group identified equipotent cycloaliphatic amides, an enantioselective preference for chiral amides, and phenyl substitution patterns (e.g., 2-methyl-3-fluoro) that increased potency. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.11.048

文献信息

• Amides of 4-hydroxy-8-methanesulfonylamino-quinoline-2-carboxylic acid as zinc-dependent inhibitors of Lp-PLA2
  作者：Yi Hu、Emme C.K. Lin、Lan M. Pham、Julia Cajica、Christopher M. Amantea、Eric Okerberg、Heidi E. Brown、Allister Fraser、Lingling Du、Yasushi Kohno、Junichi Ishiyama、John W. Kozarich、Kevin R. Shreder

  DOI：10.1016/j.bmcl.2012.11.048

  日期：2013.3

  AX10479, the phenyl amide of 4-hydroxy-8-methanesulfonylamino-quinoline-2-carboxylic acid, was identified as a Zn2+-dependent, 27 nM inhibitor of human plasma Lp-PLA(2). Structure-activity relationship studies focused on the AX10479 2-phenylamide group identified equipotent cycloaliphatic amides, an enantioselective preference for chiral amides, and phenyl substitution patterns (e.g., 2-methyl-3-fluoro) that increased potency. (c) 2012 Elsevier Ltd. All rights reserved.