N-(4-甲氧基苯基)-N-甲基喹唑啉-4-胺 | 827030-63-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: N-(4-甲氧基苯基)-N-甲基喹唑啉-4-胺
• 英文名称: N-(4-methoxyphenyl)-N-methylquinazolin-4-amine
• 英文别名: (4-methoxy-phenyl)-methyl-quinazolin-4-yl-amine
• CAS: 827030-63-7
• 化学式: C₁₆H₁₅N₃O
• 分子量: 265.315
• InChiKey: DSOZHEAZGXTKSL-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：
  0.12
• 拓扑面积：
  38.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-羟基喹唑啉 在 三乙胺 、 三氯氧磷 作用下， 以 异丙醇 、 甲苯 为溶剂， 反应 16.0h， 生成 N-(4-甲氧基苯基)-N-甲基喹唑啉-4-胺
  参考文献：
  名称：

  取代喹唑啉在癌症治疗中与多个靶点相互作用的潜力

  摘要：

  基于喹唑啉的抗神经胶质瘤药物的功效归因于它们对微管动力学的影响。 1,2描述了喹唑啉作为多种细胞内靶点（包括微管和多种 RTK）的有效抑制剂的设计、合成和生物学评价。除了已知喹唑啉1和2能够引起微管解聚之外，还发现它们是 EGFR、VEGFR-2 和 PDGFR-β 的低纳摩尔抑制剂。 1-3和9-10观察到EGFR 的低纳摩尔抑制。化合物1和4抑制VEGFR-2激酶的活性优于或等于舒尼替尼。此外，在 CAM 血管生成测定中，化合物1和2与舒尼替尼具有相似的效力。本研究中化合物的多靶点活性表明喹唑啉可以影响多种途径，并可能导致这些药物因其针对多个靶点的活性而具有抗肿瘤潜力。

  DOI：

  10.1016/j.bmc.2021.116061

文献信息

• COMPOUNDS AND THERAPEUTICAL USE THEREOF
  申请人：Cai Xiong Sui

  公开号：US20070244113A1

  公开（公告）日：2007-10-18

  Disclosed are 4-arylamino-quinazolines and analogs thereof effective as activators of caspases and inducers of apoptosis. The compounds of this invention are useful in the treatment of a variety of clinical conditions in which uncontrolled growth and spread of abnormal cells occurs.

  本发明揭示了4-芳氨基喹唑啉及其类似物，可有效激活半胱氨酸蛋白酶并诱导细胞凋亡。本发明的化合物在治疗各种临床情况中具有用途，其中异常细胞的不受控制的生长和扩散。
• Compounds and therapeutical use thereof
  申请人：Cai Xiong Sui

  公开号：US20050137213A1

  公开（公告）日：2005-06-23

  Disclosed are 4-arylamino-quinazolines and analogs thereof effective as activators of caspases and inducers of apoptosis. The compounds of this invention are useful in the treatment of a variety of clinical conditions in which uncontrolled growth and spread of abnormal cells occurs.

  本发明揭示了4-芳基氨基喹唑啉及其类似物，它们有效地激活半胱氨酸蛋白酶并诱导细胞凋亡。本发明的化合物在治疗各种临床病症中具有用途，其中发生异常细胞的不受控制的生长和扩散。
• 4-arylamino-quinazolines and analogs as activators of caspases and inducers of apoptosis and the use thereof
  申请人：Myriad Pharmaceuticals, Inc.

  公开号：US07618975B2

  公开（公告）日：2009-11-17

  Disclosed are 4-arylamino-quinazolines and analogs thereof effective as activators of caspases and inducers of apoptosis. The compounds of this invention are useful in the treatment of a variety of clinical conditions in which uncontrolled growth and spread of abnormal cells occurs.

  本发明揭示了4-芳基氨基喹唑啉及其类似物，其作为caspase激活剂和诱导凋亡剂具有有效性。本发明的化合物在治疗各种临床病症中有用，其中发生异常细胞的不受控制的生长和扩散。
• COMPOUNDS AND THERAPEUTICAL USES THEREOF
  申请人：Myrexis, Inc.

  公开号：US20130029942A1

  公开（公告）日：2013-01-31

  Disclosed are 4-arylamino-quinazolines and analogs thereof that are effective as activators of caspases and inducers of apoptosis. The compounds of this invention are useful in the treatment of a variety of clinical conditions in which uncontrolled growth and spread of abnormal cells occurs.

  本发明揭示了4-芳基氨基喹唑啉及其类似物，它们有效地激活半胱氨酸蛋白酶并诱导细胞凋亡。该发明的化合物在治疗各种临床病症中具有用途，其中包括发生异常细胞无控制生长和扩散的情况。
• Discovery of 2-Chloro-<i>N</i>-(4-methoxyphenyl)-<i>N</i>-methylquinazolin-4-amine (EP128265, MPI-0441138) as a Potent Inducer of Apoptosis with High In Vivo Activity
  作者：Nilantha Sirisoma、Shailaja Kasibhatla、Azra Pervin、Hong Zhang、Songchun Jiang、J. Adam Willardsen、Mark B. Anderson、Vijay Baichwal、Gary G. Mather、Kevin Jessing、Raouf Hussain、Khanh Hoang、Christopher M. Pleiman、Ben Tseng、John Drewe、Sui Xiong Cai

  DOI：10.1021/jm8003653

  日期：2008.8.1

  Using a live cell, high-throughput caspase-3 activator assay, we have identified a novel series of 4-anilinoquinazolines as inducers of apoptosis. In this report, we discuss the discovery of 2-chloro-N-(4-methoxyphenyl)-N-methylquinazolin-4-amine, compound 2b (EP128265, MPI-0441138) as a highly active inducer of apoptosis (EC(50) for caspase activation of 2 nM) and as a potent inhibitor of cell proliferation (GI(50) of 2 nM) in T47D cells. Compound 2b inhibited tubulin polymerization, was effective in cells overexpressing ABC transporter Pgp-1, and was efficacious in the MX-1 human breast and PC-3 prostate cancer mouse models. In contrast to the SAR of 4-anilinoquinazolines as EGFR kinase inhibitors, the methyl group on the nitrogen linker was essential for the apoptosis-inducing activity of 4-anilinoquinazolines and substitution in the 6- and 7-positions of the quinazoline core structure decreased potency.