4-(quinazolin-4-ylamino)benzoic acid | 33683-30-6

• 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)benzoic acid
• CAS: 33683-30-6
• 化学式: C₁₅H₁₁N₃O₂
• mdl: MFCD02322970
• 分子量: 265.271
• InChiKey: SGTLIIKTRIMNPW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 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)benzoic acid 、 5-benzyl-2-(piperazin-1-yl)pyrimidine 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以76%的产率得到(4-(5-benzylpyrimidin-2-yl)piperazin-1-yl)(4-(quinazolin-4-ylamino)phenyl)methanone
  参考文献：
  名称：

  Discovery, synthesis, and investigation of the antitumor activity of novel piperazinylpyrimidine derivatives

  摘要：

  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.

  DOI：

  10.1016/j.ejmech.2011.02.057
• 作为产物：
  描述：

  4-氯喹唑啉 在 sodium hydroxide 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 生成 4-(quinazolin-4-ylamino)benzoic acid
  参考文献：
  名称：

  异羟肟酸衍生物对血管生成模拟的影响

  摘要：

  摘要 — 血管生成拟态，即由高度恶性表型的肿瘤细胞形成的血管通道，目前被认为是肿瘤的额外血液供应系统。体内实验研究反复证明，在血管密度低的肿瘤区域形成血管通道。据推测，这些通道在肿瘤内形成的网络可以维持体内平衡并防止其内的早期坏死。在这项工作中，研究了基于一个分子中喹唑啉和异羟肟酸组合的双功能化合物抑制肿瘤细胞迁移和血管生成拟态的能力。

  DOI：

  10.1134/s106816202002017x

文献信息

• 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。
• Compositions and methods for modulating gated ion channels
  申请人：Babinski Kazimierz

  公开号：US20070197509A1

  公开（公告）日：2007-08-23

  The present invention relates to compositions and methods to modulate the activity of gated ion channels.

  本发明涉及用于调节门控离子通道活性的组合物和方法。
• WO2007/71055
  申请人：——

  公开号：——

  公开（公告）日：——
• EP2708532
  申请人：——

  公开号：——

  公开（公告）日：——
• Effect of Derivatives of Hydroxamic Acids on Vasculogenic Mimicry
  作者：A. A. Vartanian、D. A. Khochenkov、Yu. A. Khochenkova、Yu. S. Machkova、D. S. Khachatryan、A. V. Kolotaev、A. N. Balaev、K. A. Ohmanovich、V. N. Osipov

  DOI：10.1134/s106816202002017x

  日期：2020.3

  formation of a network of these channels inside the tumor maintains homeostasis and prevents early necrosis within it. In this work, bifunctional compounds based on a combination of quinazoline and hydroxamic acid in one molecule were examined for the ability to inhibit the migration of tumor cells and vasculogenic mimicry.

  摘要 — 血管生成拟态，即由高度恶性表型的肿瘤细胞形成的血管通道，目前被认为是肿瘤的额外血液供应系统。体内实验研究反复证明，在血管密度低的肿瘤区域形成血管通道。据推测，这些通道在肿瘤内形成的网络可以维持体内平衡并防止其内的早期坏死。在这项工作中，研究了基于一个分子中喹唑啉和异羟肟酸组合的双功能化合物抑制肿瘤细胞迁移和血管生成拟态的能力。