8-bromo-5-methyl-4-oxo-1,4-dihydroquinoline-2-carboxylic acid ethyl ester | 1206912-66-4

• 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: 8-bromo-5-methyl-4-oxo-1,4-dihydroquinoline-2-carboxylic acid ethyl ester
• 英文别名: ethyl 8-bromo-5-methyl-4-oxo-1H-quinoline-2-carboxylate
• CAS: 1206912-66-4
• 化学式: C₁₃H₁₂BrNO₃
• 分子量: 310.147
• InChiKey: KXUSDLIFRJZHGA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(4-吗啉基)苯胺 、 8-bromo-5-methyl-4-oxo-1,4-dihydroquinoline-2-carboxylic acid ethyl ester 在 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 1.03h， 以76%的产率得到8-bromo-5-methyl-4-oxo-1,4-dihydroquinoline-2-carboxylic acid (4-morpholin-4-ylphenyl)amide
  参考文献：
  名称：

  De Novo Design of a Picomolar Nonbasic 5-HT_1B Receptor Antagonist

  摘要：

  We describe herein the discovery of novel, de novo designed, 5-HT1B receptor antagonists that lack a basic moiety and that provide improved hERG and in vitro phospholipidosis profiles. We used a known 5-HT1B antagonist template as our starting point and focused on replacing the piperazine moiety. Pyrazole-based ideas were designed and synthesized among a small library of piperazine replacements. To our knowledge, these are the first potent, nonbasic, functionally active antagonists of the 5-HT1B receptor.

  DOI：

  10.1021/jm901200t
• 作为产物：
  描述：

  (E)-2-(2-bromo-5-methylphenylamino)but-2-enedioic acid diethyl ester 以 diphenyl ether-biphenyl eutectic 为溶剂， 反应 0.12h， 以84%的产率得到8-bromo-5-methyl-4-oxo-1,4-dihydroquinoline-2-carboxylic acid ethyl ester
  参考文献：
  名称：

  De Novo Design of a Picomolar Nonbasic 5-HT_1B Receptor Antagonist

  摘要：

  We describe herein the discovery of novel, de novo designed, 5-HT1B receptor antagonists that lack a basic moiety and that provide improved hERG and in vitro phospholipidosis profiles. We used a known 5-HT1B antagonist template as our starting point and focused on replacing the piperazine moiety. Pyrazole-based ideas were designed and synthesized among a small library of piperazine replacements. To our knowledge, these are the first potent, nonbasic, functionally active antagonists of the 5-HT1B receptor.

  DOI：

  10.1021/jm901200t

文献信息

• De Novo Design of a Picomolar Nonbasic 5-HT_1B Receptor Antagonist
  作者：David A. Nugiel、Jennifer R. Krumrine、Daniel C. Hill、James R. Damewood、Peter R. Bernstein、Cynthia D. Sobotka-Briner、JianWei Liu、Anna Zacco、M. Edward Pierson

  DOI：10.1021/jm901200t

  日期：2010.2.25

  We describe herein the discovery of novel, de novo designed, 5-HT1B receptor antagonists that lack a basic moiety and that provide improved hERG and in vitro phospholipidosis profiles. We used a known 5-HT1B antagonist template as our starting point and focused on replacing the piperazine moiety. Pyrazole-based ideas were designed and synthesized among a small library of piperazine replacements. To our knowledge, these are the first potent, nonbasic, functionally active antagonists of the 5-HT1B receptor.