2-(氯甲基)-N-(4-甲氧基苯基)-N-甲基喹唑啉-4-胺 | 827031-05-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 2-(氯甲基)-N-(4-甲氧基苯基)-N-甲基喹唑啉-4-胺
• 英文名称: 2-chloromethyl-N-(4-methoxyphenyl)-N-methylquinazolin-4-amine
• 英文别名: (2-chloromethyl-quinazolin-4-yl)-(4-methoxy-phenyl)-methyl-amine；2-(chloromethyl)-N-(4-methoxyphenyl)-N-methylquinazolin-4-amine
• CAS: 827031-05-0
• 化学式: C₁₇H₁₆ClN₃O
• 分子量: 313.787
• InChiKey: HADKEDUVFJBONA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  38.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(氯甲基)-N-(4-甲氧基苯基)-N-甲基喹唑啉-4-胺 在 sodium hydroxide 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 24.0h， 以44%的产率得到2-hydroxymethyl-N-(4-methoxyphenyl)-N-methylquinazolin-4-amine
  参考文献：
  名称：

  Discovery of N-(4-Methoxyphenyl)-N,2-dimethylquinazolin-4-amine, a Potent Apoptosis Inducer and Efficacious Anticancer Agent with High Blood Brain Barrier Penetration

  摘要：

  As a continuation of our structure-activity relationship (SAR) studies on 4-anilinoquinazolines as potent apoptosis inducers and to identify anticancer development candidates, we explored the replacement of the 2-Cl group in our lead compound 2-chloro-N-(4-methoxyphenyl)-N-methylquinazolin-4-amine (6b, EP 128265, MPI-0441138) by other functional groups. This SAR study and lead optimization resulted in the identification of N-(4-methoxyphenyl)-N,2-dimethylquinazolin-4-amine (6h EP128495, MPC-6827) as an anticancer clinical candidate. Compound 6h was found to be a potent apoptosis inducer with EC50 of 2 nM in our cell-based apoptosis induction assay. It also has excellent blood brain barrier penetration, and is highly efficacious in human MX-1 breast and other mouse xenograft cancer models.

  DOI：

  10.1021/jm801315b
• 作为产物：
  描述：

  N-甲基-P-氨基苯甲醚 、 4-氯-2-(氯甲基)喹唑啉 在 盐酸 作用下， 以 异丙醇 为溶剂， 生成 2-(氯甲基)-N-(4-甲氧基苯基)-N-甲基喹唑啉-4-胺
  参考文献：
  名称：

  WO2006/74187

  摘要：

  公开号：

文献信息

• PHARMACEUTICAL COMPOUNDS AS INHIBITORS OF CELL PROLIFERATION AND THE USE THEREOF
  申请人：ANDERSON MARK B.

  公开号：US20100068197A1

  公开（公告）日：2010-03-18

  Disclosed are compounds of Formula I effective as cytotoxic agents. 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.

  揭示的是作为细胞毒性剂有效的I式化合物。本发明的化合物在治疗多种临床病况中是有用的，这些病况中发生异常细胞的不受控制的生长和扩散。
• [EN] PHARMACEUTICAL COMPOUNDS AS CYTOTOXIC AGENTS AND THE USE THEREOF<br/>[FR] COMPOSÉS PHARMACEUTIQUES EN TANT QU'AGENTS CYTOTOXIQUES ET LEUR UTILISATION
  申请人：MYRIAD PHARMACEUTICALS INC

  公开号：WO2010006115A1

  公开（公告）日：2010-01-14

  Disclosed are compounds effective as cytotoxic agents. 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.

  本发明揭示了有效的细胞毒性剂化合物。本发明的化合物在治疗出现异常细胞不受控制生长和扩散的各种临床病症方面具有用途。
• 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。