4-((quinazolin-4-ylamino)methyl)benzoic acid | 305835-75-0

• 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-((quinazolin-4-ylamino)methyl)benzoic acid
• 英文别名: 4-[(Quinazolin-4-ylamino)methyl]benzoic acid
• CAS: 305835-75-0
• 化学式: C₁₆H₁₃N₃O₂
• 分子量: 279.298
• InChiKey: RLYCYSCZYWTOEU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  75.1
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-((quinazolin-4-ylamino)methyl)benzoic acid 在 盐酸 作用下， 生成 N-(2-Amino-ethyl)-4-(quinazolin-4-ylaminomethyl)-benzamide
  参考文献：
  名称：

  Synthesis of two bi-functional ligands for the QUEST three-hybrid system

  摘要：

  The synthesis is described for two bi-functional ligands (1) and (2) that have been used as chemical inducers of dimerization for QUEST,(1) a three-hybrid system designed to detect novel enzyme activity in vivo. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01202-8
• 作为产物：
  描述：

  4-[(p-methoxycarbonylbenzyl)amino]quinazoline 在 水 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成 4-((quinazolin-4-ylamino)methyl)benzoic acid
  参考文献：
  名称：

  4-Aminoquinazoline Derivatives and Uses Thereof

  摘要：

  本发明提供了一种具有以下化学结构的4-氨基喹唑啉衍生物，以及其用途。药理实验证明，根据本发明的化合物或其盐不仅对组蛋白去乙酰化酶具有明显的抑制作用，而且对某些肿瘤细胞具有更强的分化诱导和抗增殖活性。它可用于治疗与细胞分化和增殖相关的癌症和疾病。特别是对白血病和实体肿瘤观察到了出色的疗效。药物实验证明，根据本发明的化合物或其盐毒性较小。

  公开号：

  US20140235633A1

文献信息

• EP2708532
  申请人：——

  公开号：——

  公开（公告）日：——
• Discovery, synthesis, and investigation of the antitumor activity of novel piperazinylpyrimidine derivatives
  作者：Hassan M. Shallal、Wade A. Russu

  DOI：10.1016/j.ejmech.2011.02.057

  日期：2011.6

  Protein kinases play several pertinent roles in cell proliferation, and targeting these proteins has been shown to be a successful strategy toward controlling different malignancies. Despite the great discovery stories during the last two decades, there is still a demand for anticancer small molecules with the potential of being selective on both the protein kinase and/or the cellular level. A series of novel piperazinylpyrimidine compounds were synthesized and tested for their potential to selectively inhibit the growth of certain tumor cell lines included within the NCI-60 cell line panel. MDA-MB-468, a triple-negative/basal-like breast carcinoma, cell line was among the most sensitive cell lines towards compounds 4 and 15. The three most interesting compounds identified in cellular screens (4, 15, and 16) were subjected to kinase profiling and found to have an interesting selective tendency to target certain kinase subfamily members; PDGFR, CK1, RAF and others. Compound 4 showed a selective tendency to bind to and/or inhibit the function of certain KIT and PDGFRA mutants compared to their wild-type isoforms. Piperazinylpyrimidine based derivatives represent a new class of selective kinase inhibitors. Significantly 4 is more potent at inhibiting oncogenic mutant forms of PDGFR family kinases, which is relevant in terms of its potential use in treating tumors that have become resistant to treatment or driven by such mutations. The clinical demand for agents useful in the control of triple-negative/basal-like breast cancer justifies our interest in compound 15 which is a potent growth inhibitor of MDA-MB-468 cell line. (C) 2011 Elsevier Masson SAS. All rights reserved.
• 4-Aminoquinazoline Derivatives and Uses Thereof
  申请人：SHANGHAI INSTITUTE OF PHARMACEUTICAL INDUSTRY

  公开号：US20140235633A1

  公开（公告）日：2014-08-21

  The present invention provides a 4-aminoquinazoline derivative having the chemical structure of the following formula, and the use thereof. It is demonstrated by the pharmacological experiment that, the compound or a salt thereof according to the present invention not only has distinct inhibitory effect on histone deacetylases, but also has stronger differentiation induction and anti-proliferative activities for certain tumor cells. It can be used in the treatment of cancers and diseases related to cell differentiation and proliferation. Excellent efficacy is observed especially for leukemia and a solid tumor. As demonstrated by the animal test, the compound or a salt thereof according to the present invention is less toxic.

  本发明提供了一种具有以下化学结构的4-氨基喹唑啉衍生物，以及其用途。药理实验证明，根据本发明的化合物或其盐不仅对组蛋白去乙酰化酶具有明显的抑制作用，而且对某些肿瘤细胞具有更强的分化诱导和抗增殖活性。它可用于治疗与细胞分化和增殖相关的癌症和疾病。特别是对白血病和实体肿瘤观察到了出色的疗效。药物实验证明，根据本发明的化合物或其盐毒性较小。
• Synthesis of two bi-functional ligands for the QUEST three-hybrid system
  作者：Stephen J Baker、Steven M Firestine、David Smithrud、Frank Salinas、Stephen J Benkovic

  DOI：10.1016/s0040-4039(00)01202-8

  日期：2000.9

  The synthesis is described for two bi-functional ligands (1) and (2) that have been used as chemical inducers of dimerization for QUEST,(1) a three-hybrid system designed to detect novel enzyme activity in vivo. (C) 2000 Elsevier Science Ltd. All rights reserved.