(S)-5,7-dichloro-3-(4-methoxy-phenyl)-3-methyl-1H-quinoline-2,4-dione | 929116-39-2

• 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: (S)-5,7-dichloro-3-(4-methoxy-phenyl)-3-methyl-1H-quinoline-2,4-dione
• 英文别名: (S)-5,7-dichloro-3-(4-methoxyphenyl)-3-methylquinoline-2,4(1H,3H)-dione；(3S)-5,7-dichloro-3-(4-methoxyphenyl)-3-methyl-1H-quinoline-2,4-dione
• CAS: 929116-39-2
• 化学式: C₁₇H₁₃Cl₂NO₃
• 分子量: 350.201
• InChiKey: MPHIFJCITUWVMO-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  5,7-dichloro-3-(4-methoxy-phenyl)-3-methyl-1H-quinoline-2,4-dione 生成 (R)-5,7-dichloro-3-(4-methoxy-phenyl)-3-methyl-1H-quinoline-2,4-dione 、 (S)-5,7-dichloro-3-(4-methoxy-phenyl)-3-methyl-1H-quinoline-2,4-dione
  参考文献：
  名称：

  Discovery of 3-aryl-3-methyl-1H-quinoline-2,4-diones as a new class of selective 5-HT6 receptor antagonists

  摘要：

  A 5,7-dichloro-3-phenyl-3-methyl-quinoline-2,4-dione (11a) has been identified in a random screen as a lead for 5-HT6 antagonist. During the lead optimization process, several analogs were synthesized and their biological activities were investigated. Within this series, several compounds display high binding affinity and selectivity for the 5-HT6 receptor. In particular, 3-(4-hydroxyphenyl)-3-methyl-quinoline-2,4-dione (12f) exhibits high affinity (K-i = 12.3 nM) for 5-HT6 receptor with good selectivity over other serotonin and dopamine (D-1-D-4) receptor subtypes. In a functional adenylyl cyclase stimulation assay, this compound exhibited considerable antagonistic activity (IC50 = 0.61 mu M). (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.11.045

文献信息

• Discovery of 3-aryl-3-methyl-1H-quinoline-2,4-diones as a new class of selective 5-HT6 receptor antagonists
  作者：Churl Min Seong、Woo Kyu Park、Chul Min Park、Jae Yang Kong、No Sang Park

  DOI：10.1016/j.bmcl.2007.11.045

  日期：2008.1

  A 5,7-dichloro-3-phenyl-3-methyl-quinoline-2,4-dione (11a) has been identified in a random screen as a lead for 5-HT6 antagonist. During the lead optimization process, several analogs were synthesized and their biological activities were investigated. Within this series, several compounds display high binding affinity and selectivity for the 5-HT6 receptor. In particular, 3-(4-hydroxyphenyl)-3-methyl-quinoline-2,4-dione (12f) exhibits high affinity (K-i = 12.3 nM) for 5-HT6 receptor with good selectivity over other serotonin and dopamine (D-1-D-4) receptor subtypes. In a functional adenylyl cyclase stimulation assay, this compound exhibited considerable antagonistic activity (IC50 = 0.61 mu M). (c) 2007 Elsevier Ltd. All rights reserved.