2-[2-(4-bromo-phenyl)-propionylamino]-4,6-dichloro-benzoic acid methyl ester | 883244-28-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-[2-(4-bromo-phenyl)-propionylamino]-4,6-dichloro-benzoic acid methyl ester
• 英文别名: 2-[2-(4-bromo-phenyl)-propionylamino]-4,6-dichlorobenzoic acid methyl ester；methyl 2-[2-(4-bromophenyl)propanoylamino]-4,6-dichlorobenzoate
• CAS: 883244-28-8
• 化学式: C₁₇H₁₄BrCl₂NO₃
• 分子量: 431.113
• InChiKey: QLGNUENWCFBJJR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  2.0
• 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

• 作为反应物：
  描述：

  2-[2-(4-bromo-phenyl)-propionylamino]-4,6-dichloro-benzoic acid methyl ester 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 以18%的产率得到3-(4-bromo-phenyl)-5,7-dichloro-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
• 作为产物：
  描述：

  α-methyl 4-bromophenylacetyl chloride 、 2-amino-4,6-dichlorobenzoic acid methyl ester 以 二氯甲烷 为溶剂， 以9.31 g的产率得到2-[2-(4-bromo-phenyl)-propionylamino]-4,6-dichloro-benzoic acid methyl ester
  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

• 3-aryl--3-methyl-quinoline-2, 4-diones, preparation method thereof, and pharmaceutical composition containing the same
  申请人：Seong Churlmin

  公开号：US20060084676A1

  公开（公告）日：2006-04-20

  The present invention relates to compounds of 3-aryl-3-methyl-quinoline-2,4-diones acting as a 5HT6 receptor antagonist, a preparation method thereof, and a pharmaceutical composition containing the same for treatment of the central nervous system disorders. The compounds of 3-aryl-3-methyl-quinoline-2,4-diones according to the present invention may be valuably used for treatment of a 5HT6 receptor relating disorders because of its excellent binding affinity for the 5HT6 receptor and excellent selectivity for the 5HT6 receptor over other receptors.

  本发明涉及作为5HT6受体拮抗剂的3-芳基-3-甲基喹啉-2,4-二酮化合物，其制备方法以及含有该化合物的用于治疗中枢神经系统疾病的药物组合物。根据本发明的3-芳基-3-甲基喹啉-2,4-二酮化合物可用于治疗与5HT6受体相关的疾病，因为其对5HT6受体具有优异的结合亲和力，并且对5HT6受体具有优异的选择性，而且相对于其他受体具有优异的选择性。
• 3-aryl-3-methyl-quinoline-2,4-diones, preparation method thereof and pharmaceutical composition containing same
  申请人：KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY

  公开号：EP1650190A1

  公开（公告）日：2006-04-26

  The present invention relates to compounds of 3-aryl-3-methyl-quinoline-2,4-diones , or a pharmaceutically acceptable salt thereof acting as a 5HT6 receptor antagonist, a preparation method thereof, and a pharmaceutical composition containing the same for treatment of the central nervous system disorders. The compounds of 3-aryl-3-methyl-quinoline-2,4-diones according to the present invention may be valuably used for treatment of a 5HT6 receptor relating disorders because of its excellent binding affinity for the 5HT6 receptor and excellent selectivity for the 5HT6 receptor over other receptors.

  本发明涉及3-芳基-3-甲基喹啉-2,4-二酮化合物或其药用可接受盐，作为5HT6受体拮抗剂，其制备方法以及含有该化合物的用于治疗中枢神经系统疾病的药物组合物。根据本发明的3-芳基-3-甲基喹啉-2,4-二酮化合物可用于治疗与5HT6受体相关的疾病，因为其对5HT6受体具有优异的结合亲和力，并且对于其他受体具有优异的选择性。
• N-Substituted-1H-Quinoline-2,4-Diones, Preparation Method Thereof, And Pharmaceutical Composition Containing The Same
  申请人：Seong Churlmin

  公开号：US20080275058A1

  公开（公告）日：2008-11-06

  The present invention relates to compounds of N-substituted -1H-quinoline-2,4-diones acting as a 5HT6 receptor antagonist, a preparation method thereof, and a pharmaceutical composition containing the same for treatment of the central nervous system disorders. The compounds of N-substituted-1H-quinoline-2,4-diones according to the present invention have excellent binding affinity for the 5HT6 receptor and excellent selectivity for the 5HT6 receptor over other receptors. Also, the compounds reverse a disruption of PPI by methamphetamine and don't show rotatod deficit in mice. Thereof the compounds according to the present invention may be valuably used for treatment if a 5HT6 receptor relating disorder

  本发明涉及N-取代-1H-喹啉-2,4-二酮化合物，其作为5HT6受体拮抗剂，其制备方法以及含有该化合物的制剂，用于治疗中枢神经系统疾病。根据本发明的N-取代-1H-喹啉-2,4-二酮化合物具有优异的5HT6受体结合亲和力和对5HT6受体的优异选择性。此外，这些化合物能够逆转甲基苯丙胺引起的PPI破坏，并且在小鼠中不表现出旋转缺陷。因此，根据本发明的化合物可以有价值地用于治疗与5HT6受体相关的疾病。
• 3-aryl-3-methyl-quinoline-2, 4-diones, preparation method thereof, and pharmaceutical composition containing the same
  申请人：Korea Research Institute of Chemical Technology

  公开号：US07592457B2

  公开（公告）日：2009-09-22

  The present invention relates to compounds of 3-aryl-3-methyl-quinoline-2,4-diones acting as a 5HT6 receptor antagonist, a preparation method thereof, and a pharmaceutical composition containing the same for treatment of the central nervous system disorders. The compounds of 3-aryl-3-methyl-quinoline-2,4-diones according to the present invention may be valuably used for treatment of a 5HT6 receptor relating disorders because of its excellent binding affinity for the 5HT6 receptor and excellent selectivity for the 5HT6 receptor over other receptors.

  本发明涉及3-芳基-3-甲基-喹啉-2,4-二酮化合物，其作为5HT6受体拮抗剂，其制备方法以及含有该化合物的制药组合物，用于治疗中枢神经系统疾病。本发明所述的3-芳基-3-甲基-喹啉-2,4-二酮化合物因其对5HT6受体的优异结合亲和力和对5HT6受体与其他受体的优异选择性，可用于治疗与5HT6受体相关的疾病。
• N-SUBSTITUTED-1H-QUINOLINE-2, 4-DIONES, PREPARATION METHOD THEREOF, AND PHARMACEUTICAL COMPOSITION CONTAINING THE SAME
  申请人：KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY

  公开号：EP1954689A1

  公开（公告）日：2008-08-13