4-((2-chloroquinazolin-4-yl)(methyl)amino)phenol

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 4-((2-chloroquinazolin-4-yl)(methyl)amino)phenol
• 英文别名: 2-chloro-N-(4-hydroxyphenyl)-N-methylquinazolin-4-amine；(2-chloro-quinazolin-4-yl)-(4-hydroxyphenyl)-methylamine；4-[(2-chloroquinazolin-4-yl)-methylamino]phenol
• 化学式: C₁₅H₁₂ClN₃O
• 分子量: 285.733
• InChiKey: AUIIPISVOIPEAT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  49.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-((2-chloroquinazolin-4-yl)(methyl)amino)phenol 在 caesium carbonate 、 三乙胺 、 三氯氧磷 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.25h， 生成
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Novel Substituted 4‐Anilinoquinazolines as Antitumor Agents

  摘要：

  Eleven novel 4‐anilinoquinazoline derivatives were synthesized and evaluated for their in vitro antiproliferative activity. Among them, compound 9a exhibited the best potency, with IC50 values of 25−682 nm against various types of cancer cell lines. In addition, 9a was confirmed that it could arrest the cell cycle at G2/M phase and trigger apoptosis. Indirect immunofluorescence staining revealed its antitubulin property. Importantly, 9a significantly inhibited tumor growths in SM‐7721 xenograft models (57.0% tumor mass change) without causing significant loss of body weight, suggesting that 9a is a promising new anticancer agent to be developed.

  DOI：

  10.1111/cbdd.12706
• 作为产物：
  描述：

  4-(甲氧基甲氧基)苯胺 在 盐酸 、 sodium acetate 、 sodium hydride 作用下， 以 四氢呋喃 、 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.25h， 生成 4-((2-chloroquinazolin-4-yl)(methyl)amino)phenol
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Novel Substituted 4‐Anilinoquinazolines as Antitumor Agents

  摘要：

  Eleven novel 4‐anilinoquinazoline derivatives were synthesized and evaluated for their in vitro antiproliferative activity. Among them, compound 9a exhibited the best potency, with IC50 values of 25−682 nm against various types of cancer cell lines. In addition, 9a was confirmed that it could arrest the cell cycle at G2/M phase and trigger apoptosis. Indirect immunofluorescence staining revealed its antitubulin property. Importantly, 9a significantly inhibited tumor growths in SM‐7721 xenograft models (57.0% tumor mass change) without causing significant loss of body weight, suggesting that 9a is a promising new anticancer agent to be developed.

  DOI：

  10.1111/cbdd.12706

文献信息

• Synthesis, in vitro and in vivo evaluation of novel substituted N-(4-(2-(4-benzylpiperazin-1-yl)ethoxy)phenyl)-N-methyl-quinazolin-4-amines as potent antitumor agents
  作者：Dong Cao、Xiaoyan Wang、Lei Lei、Liang Ma、Fang Wang、Chunyu Wang、Minghai Tang、Wei Xiang、Taijin Wang、Hongyang Li、Lijuan Chen

  DOI：10.1016/j.bmcl.2016.03.016

  日期：2016.4

  A novel series of substituted N-(4-(2-(4-benzylpiperazin-1-yl)ethoxy)phenyl)-N-methylquinazolin-4-amines were synthesized and evaluated for their in vitro antiproliferative activity. Among them, compound 7a exhibited the best potency, with IC50 values of 0.029–0.147 μM against four types of cancer cell lines. In addition, 7a was confirmed that it could arrest the cell cycle at G2/M phase and trigger

  合成了一系列新的取代的N-（4-（2-（4-苄基哌嗪-1-基）乙氧基）苯基）-N-甲基喹唑啉-4-胺，并评估了它们的体外抗增殖活性。其中，化合物7a表现出最佳效能，对四种类型的癌细胞系的IC 50值为0.029-0.147μM。另外，证实了7a可以阻止细胞周期处于G 2 / M期并触发细胞凋亡。间接免疫荧光染色显示其抗微管蛋白特性。重要的是，7a显着抑制了HepG2异种移植模型中的肿瘤生长，而没有引起体重的显着降低，这表明7a 是有前途的新型抗癌药。
• 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。
• METHOD OF TREATING BRAIN CANCER
  申请人：Cai Sui Xiong

  公开号：US20080051398A1

  公开（公告）日：2008-02-28

  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, and in particular to the use of these compounds in treating brain cancer.

  本发明涉及4-芳基氨基喹唑啉及其类似物，其有效激活caspases并诱导细胞凋亡。本发明的化合物可用于治疗各种临床病症，其中发生异常细胞的不受控制的生长和扩散，特别是用于治疗脑癌。
• 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。