4-(3-chloroanilino)quinazoline hydrochloride | 146871-70-7

• 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: 4-(3-chloroanilino)quinazoline hydrochloride
• 英文别名: N-(3-chlorophenyl)quinazolin-4-amine Hydrochloride；N-(3-chlorophenyl)quinazolin-4-amine;hydrochloride
• CAS: 146871-70-7
• 化学式: C₁₄H₁₀ClN₃*ClH
• 分子量: 292.167
• InChiKey: KJSNIHYRHGBGAQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.45
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  37.8
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-羟基喹唑啉 在 2,3-二甲基苯胺 、 三氯氧磷 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 4.5h， 生成 4-(3-chloroanilino)quinazoline hydrochloride
  参考文献：
  名称：

  Tyrphostins IV—Highly potent inhibitors of EGF receptor kinase. Structure-activity relationship study of 4-anilidoquinazolines

  摘要：

  Potent 4-anilido-substituted quinazolines which potently inhibit epidermal growth factor receptor (EGFR) kinase were prepared. Structure-activity relationship studies reveal high sensitivity to substitution at the aniline ring. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0968-0896(96)00107-1

文献信息

• Tyrosine kinase inhibitors. 5. Synthesis and structure-activity relationships for 4-[(phenylmethyl)amino]- and 4-(phenylamino)quinazolines as potent adenosine 5'-triphosphate binding site inhibitors of the tyrosine kinase domain of the epidermal growth factor receptor.
  作者：Gordon W. Rewcastle、William A. Denny、Alexander J. Bridges、Hairong Zhou、Donna R. Cody、Amy McMichael、David W. Fry

  DOI：10.1021/jm00018a008

  日期：1995.9

  A series of 4-substituted quinazolines and related compounds have been prepared and evaluated for their ability to inhibit the tyrosine kinase activity of the epidermal growth factor receptor on a phospholipase C-gamma 1-derived substrate. The results show a narrow structure-activity relationship (SAR) for the basic ring system, with quinazoline being the preferred chromophore and benzylamino and anilino

  已经制备了一系列的4-取代的喹唑啉和相关化合物，并评估了它们在磷脂酶C-γ1衍生的底物上抑制表皮生长因子受体的酪氨酸激酶活性的能力。结果表明基本环系统的结构-活性关系（SAR）狭窄，喹唑啉是优选的生色团，苄基氨基和苯胺基是优选的侧链。在4-苯胺基系列中，苯环的3-位被小的亲脂性吸电子基团取代提供了具有增强效价的类似物。研究了两个系列的化合物[4-（苯甲基）氨基和4-（3-溴苯基）氨基]，以确定喹唑啉取代基的SAR。在更具活性的4-（3-溴苯基）氨基系列中，给电子基团（NH2，OMe）在6或7位的活性增加，其模式与对喹唑啉环的8位附近的高电子密度的要求一致。6,7-二甲氧基衍生物是这两个系列中最有效的，而4-（3-溴苯基）氨基衍生物（3）的IC50为0.029 nM，是迄今为止最有效的酪氨酸激酶活性抑制剂。表皮生长因子受体酶的作用。
• The preparation and sar of 4-(anilino), 4-(phenoxy), and 4-(thiophenoxy)-quinazolines: Inhibitors of p56lck and EGF-R tyrosine kinase activity
  作者：Michael R. Myers、Natalie N. Setzer、Alfred.P. Spada、Allison L. Zulli、Chin-Yi J. Hsu、Asher Zilberstein、Susan E. Johnson、Linda E. Hook、Mary V. Jacoski

  DOI：10.1016/s0960-894x(97)00034-6

  日期：1997.2

  We report herein our preliminary results of a SAR study of quinazoline-based inhibitors of p56(lck) and EGF-R tyrosine kinase activity.(1) The most potent inhibitor of p56(lck) identified, RPR-108518A (10), has an IC50 of 0.50 mu M. The 3-chlorophenoxy- and 3-chlorothiophenoxy- derivatives 5 and 6 were also shown to be extremely potent EGF-R inhibitors. (C) 1997, Elsevier Science Ltd.
• Therapeutic preparations containing quinazoline derivatives
  申请人：ZENECA LIMITED

  公开号：EP0520722B1

  公开（公告）日：1996-12-27
• Tyrphostins IV—Highly potent inhibitors of EGF receptor kinase. Structure-activity relationship study of 4-anilidoquinazolines
  作者：Aviv Gazit、Jeffrey Chen、Harald App、Gerald McMahon、Peter Hirth、Irit Chen、Alexander Levitzki

  DOI：10.1016/0968-0896(96)00107-1

  日期：1996.8

  Potent 4-anilido-substituted quinazolines which potently inhibit epidermal growth factor receptor (EGFR) kinase were prepared. Structure-activity relationship studies reveal high sensitivity to substitution at the aniline ring. Copyright (C) 1996 Elsevier Science Ltd