6-Bromo-N-[2-(4-chlorophenyl)ethyl]quinazolin-4-amine | 124427-64-1

• 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: 6-Bromo-N-[2-(4-chlorophenyl)ethyl]quinazolin-4-amine
• CAS: 124427-64-1
• 化学式: C₁₆H₁₃BrClN₃
• 分子量: 362.656
• InChiKey: CYHYRQVOQVBQSD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  37.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  6-溴-4-羟基喹唑啉 在 三乙胺 、 三氯氧磷 作用下， 以 异丙醇 为溶剂， 生成 6-Bromo-N-[2-(4-chlorophenyl)ethyl]quinazolin-4-amine
  参考文献：
  名称：

  Structure–activity relationships of quinazoline derivatives: dual-acting compounds with inhibitory activities toward both TNF-α production and T Cell proliferation

  摘要：

  We synthesized 4-chlorophenethylaminoquinazoline derivatives and evaluated their inhibitory activities toward both TNF-alpha production and T cell proliferation responses; Compound 2f, containing a piperazine ring at the C(7)-position of the quinazoline ring, exhibited more potent inhibitory activities toward both than the lead compound 1a. A smaller N-substituent in the piperazine ring was required for inhibition of TNF-alpha production. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00718-6

文献信息

• Structure–activity relationships of quinazoline derivatives: dual-acting compounds with inhibitory activities toward both TNF-α production and T Cell proliferation
  作者：Masanori Tobe、Yoshiaki Isobe、Hideyuki Tomizawa、Mitsuhiro Matsumoto、Fumihiro Obara、Takahiro Nagasaki、Hideya Hayashi

  DOI：10.1016/s0960-894x(00)00718-6

  日期：2001.2

  We synthesized 4-chlorophenethylaminoquinazoline derivatives and evaluated their inhibitory activities toward both TNF-alpha production and T cell proliferation responses; Compound 2f, containing a piperazine ring at the C(7)-position of the quinazoline ring, exhibited more potent inhibitory activities toward both than the lead compound 1a. A smaller N-substituent in the piperazine ring was required for inhibition of TNF-alpha production. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Potent inhibitors of Huntingtin protein aggregation in a cell-based assay
  作者：Alison Rinderspacher、Maria Laura Cremona、Yidong Liu、Shi-Xian Deng、Yuli Xie、Gangli Gong、Nathalie Aulner、Udo Többen、Katherine Myers、Caty Chung、Monique Andersen、Dušica Vidović、Stephan Schürer、Lars Brandén、Ai Yamamoto、Donald W. Landry

  DOI：10.1016/j.bmcl.2009.01.087

  日期：2009.3

  A quinazoline that decreases polyglutamine aggregate burden in a cell-based assay was identified from a high-throughput screen of a chemical-compound library, provided by the NIH Molecular Libraries Small Molecule Repository (MLSMR). A structure and activity study yielded leads with submicromolar potency. (C) 2009 Elsevier Ltd. All rights reserved.
• Quinazoline derivatives useful as insecticides.
  申请人：Dow AgroSciences LLC

  公开号：EP0326329B1

  公开（公告）日：1998-10-28
• Discovery of quinazolines as a novel structural class of potent inhibitors of NF-κB activation
  作者：Masanori Tobe、Yoshiaki Isobe、Hideyuki Tomizawa、Takahiro Nagasaki、Hirotada Takahashi、Tominaga Fukazawa、Hideya Hayashi

  DOI：10.1016/s0968-0896(02)00440-6

  日期：2003.2

  We disclose here a new structural class of low-molecular-weight inhibitors of NF-kappaB activation that were designed and synthesized by starting from quinazoline derivative 6a. Structure-activity relationship (SAR) studies based on 6a elucidated the structural requirements essential for the inhibitory activity toward NF-kappaB transcriptional activation, and led to the identification of the 6-amino-4-phenethylaminoquinazoline skeleton as the basic framework. In this series of compounds, 11q, containing the 4-phenoxyphenethyl moiety at the C(4)-position, showed strong inhibitory effects on both NF-kappaB transcriptional activation and TNF-alpha production. Furthermore, 11q exhibited an anti-inflammatory effect on carrageenin-induced paw edema in rats. (C) 2002 Elsevier Science Ltd. All rights reserved.