2-((4-chlorophenyl)amino)-7,7-dimethyl-7,8-dihydroquinazolin-5(6H)-one | 1383718-71-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 2-((4-chlorophenyl)amino)-7,7-dimethyl-7,8-dihydroquinazolin-5(6H)-one
• 英文别名: 2-(4-Chloroanilino)-7,7-dimethyl-6,8-dihydroquinazolin-5-one
• CAS: 1383718-71-5
• 化学式: C₁₆H₁₆ClN₃O
• 分子量: 301.776
• InChiKey: SEHUTCGJEJEBDP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  54.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-dimethylaminomethylene-5,5-dimethylcyclohexane-1,3-dione 、 1-(4-氯苯基)胍硝酸盐(1:1) 在 三乙胺 作用下， 以 乙醇 为溶剂， 以37%的产率得到2-((4-chlorophenyl)amino)-7,7-dimethyl-7,8-dihydroquinazolin-5(6H)-one
  参考文献：
  名称：

  Discovery, synthesis, and structure–activity relationships of 2-aminoquinazoline derivatives as a novel class of metabotropic glutamate receptor 5 negative allosteric modulators

  摘要：

  A virtual screening approach using various in silico methodologies led to the discovery of 2-(m-tolylamino)-7,8-dihydroquinazolin-5(6H)-one (1) as a moderately active negative allosteric modulator (NAM) of the metabotropic glutamate receptor subtype 5 (mGluR5) showing high selectivity against the subtype mGluR1. Modifications of the parent compound by rational design yielded a series of highly potent derivatives which will serve as valuable starting points for further hit-to-lead optimization efforts toward a suitable drug candidate for the treatment of L-DOPA induced dyskinesia. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.06.049

文献信息

• [EN] METABOTROPIC GLUTAMATE RECEPTOR MODULATORS<br/>[FR] MODULATEURS DES RÉCEPTEURS GLUTAMATERGIQUES MÉTABOTROPES
  申请人：MERZ PHARMA GMBH & CO KGAA

  公开号：WO2012085166A1

  公开（公告）日：2012-06-28

  The invention relates to heterocyclic derivatives as well as their pharmaceutically acceptable salts. The invention further relates to a process for the preparation of such compounds. The compounds of the invention are mGluR5 modulators and are therefore useful for the control and prevention of acute and/or chronic neurological disorders.

  这项发明涉及杂环衍生物及其药用可接受的盐。该发明还涉及一种制备这类化合物的方法。该发明的化合物是mGluR5调节剂，因此对于控制和预防急性和/或慢性神经系统疾病是有用的。
• Discovery, synthesis, and structure–activity relationships of 2-aminoquinazoline derivatives as a novel class of metabotropic glutamate receptor 5 negative allosteric modulators
  作者：Holger Kubas、Udo Meyer、Bjoern Krueger、Mirko Hechenberger、Maksims Vanejevs、Ronalds Zemribo、Valerjans Kauss、Raisa Ambartsumova、Ilya Pyatkin、Alexey I. Polosukhin、Ulrich Abel

  DOI：10.1016/j.bmcl.2013.06.049

  日期：2013.8

  A virtual screening approach using various in silico methodologies led to the discovery of 2-(m-tolylamino)-7,8-dihydroquinazolin-5(6H)-one (1) as a moderately active negative allosteric modulator (NAM) of the metabotropic glutamate receptor subtype 5 (mGluR5) showing high selectivity against the subtype mGluR1. Modifications of the parent compound by rational design yielded a series of highly potent derivatives which will serve as valuable starting points for further hit-to-lead optimization efforts toward a suitable drug candidate for the treatment of L-DOPA induced dyskinesia. (c) 2013 Elsevier Ltd. All rights reserved.