8,8-dimethyl-2-(m-tolylamino)-7,8-dihydroquinazolin-5(6H)-one | 1383718-75-9

• 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: 8,8-dimethyl-2-(m-tolylamino)-7,8-dihydroquinazolin-5(6H)-one
• 英文别名: 8,8-Dimethyl-2-(3-methylanilino)-6,7-dihydroquinazolin-5-one
• CAS: 1383718-75-9
• 化学式: C₁₇H₁₉N₃O
• 分子量: 281.357
• InChiKey: LKNXEXHWNWMONZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 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：

  4,4-二甲基-1,3-环己二酮 在 三乙胺 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 6.0h， 生成 8,8-dimethyl-2-(m-tolylamino)-7,8-dihydroquinazolin-5(6H)-one 、 6,6-dimethyl-2-(m-tolylamino)-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

• 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.