2,N-dimethyl-N-(4-nitrophenyl)quinazolin-4-amine | 827031-34-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2,N-dimethyl-N-(4-nitrophenyl)quinazolin-4-amine
• 英文别名: (2-methyl-quinazolin-4-yl)-(4-nitro-phenyl)-methyl-amine；4-Quinazolinamine, N,2-dimethyl-N-(4-nitrophenyl)-；N,2-dimethyl-N-(4-nitrophenyl)quinazolin-4-amine
• CAS: 827031-34-5
• 化学式: C₁₆H₁₄N₄O₂
• 分子量: 294.313
• InChiKey: DIHCMDVTRMTNEH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  74.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,N-dimethyl-N-(4-nitrophenyl)quinazolin-4-amine 在 钯 crude product 、 ethyl acetate n-hexane 作用下， 以 乙酸乙酯 为溶剂， 反应 4.0h， 以to obtain the title compound (140 mg, 78%)的产率得到N-(4-aminophenyl)-N,2-dimethylquinazolin-4-amine
  参考文献：
  名称：

  COMPOUNDS AND THERAPEUTICAL USE THEREOF

  摘要：

  本发明公开了4-芳基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。本发明的化合物可用于治疗多种临床病症，其中不受控制的异常细胞生长和扩散发生。

  公开号：

  US20070208044A1
• 作为产物：
  描述：

  4-氯-2-甲基喹唑啉 、 N-甲基对硝基苯胺 在 sodium hydride 作用下， 以 DMF (N,N-dimethyl-formamide) 为溶剂， 反应 1.0h， 以67%的产率得到2,N-dimethyl-N-(4-nitrophenyl)quinazolin-4-amine
  参考文献：
  名称：

  [EN] 4-ARYLAMINO-QUINAZOLINES AS ACTIVATORS OF CASPASES AND INDUCERS OF APOPTOSIS
  [FR] COMPOSES ET LEUR UTILISATION THERAPEUTIQUE

  摘要：

  公开号：

  WO2005003100A3

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 <i>N</i>-(4-Methoxyphenyl)-<i>N</i>,2-dimethylquinazolin-4-amine, a Potent Apoptosis Inducer and Efficacious Anticancer Agent with High Blood Brain Barrier Penetration
  作者：Nilantha Sirisoma、Azra Pervin、Hong Zhang、Songchun Jiang、J. Adam Willardsen、Mark B. Anderson、Gary Mather、Christopher M. Pleiman、Shailaja Kasibhatla、Ben Tseng、John Drewe、Sui Xiong Cai

  DOI：10.1021/jm801315b

  日期：2009.4.23

  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.