N-(3,4-dimethoxyphenyl)quinazolin-4-amine

• 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: N-(3,4-dimethoxyphenyl)quinazolin-4-amine
• 化学式: C₁₆H₁₅N₃O₂
• 分子量: 281.314
• InChiKey: AVRCYOCVSOUCFT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  56.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(3,4-dimethoxyphenyl)quinazolin-4-amine 、 碘甲烷 、 sodium;hydride 以 N,N-二甲基甲酰胺 为溶剂， 以to give 2.0 mg (2%) of white solids的产率得到
  参考文献：
  名称：

  COMPOUNDS AND THERAPEUTICAL USE THEREOF

  摘要：

  本发明涉及4-芳胺基喹唑啉及其类似物，其作为caspase激活剂和凋亡诱导剂具有有效性。本发明的化合物在治疗各种临床情况中有用，其中发生异常细胞的不受控制的生长和扩散。

  公开号：

  US20080004297A1
• 作为产物：
  描述：

  4-羟基喹唑啉 在 三氯氧磷 作用下， 以 异丙醇 为溶剂， 反应 9.0h， 生成 N-(3,4-dimethoxyphenyl)quinazolin-4-amine
  参考文献：
  名称：

  Investigation of quinazolines as inhibitors of breast cancer resistance protein (ABCG2)

  摘要：

  Chemotherapy is one of the major forms of cancer treatment. Unfortunately, tumors are prone to multidrug resistance leading to failure of treatment. Breast cancer resistance protein (BCRP), the second member of ABC transporter subfamily G, has been found to play a major role in drug efflux and hence multidrug resistance. Until now, very few potent and selective BCRP inhibitors like Ko143 have been identified. In the search for more potent and selective BCRP inhibitors, we synthesized and investigated a series of differently substituted quinazoline compounds. Several variations at positions 2, 4, 6 and 7 of the quinazoline scaffold were carried out to develop a structure-activity-relationship analysis for these compounds. It was found that compounds bearing a phenyl substituent at position 2 of the 4-anilinoquinazoline scaffold were most potent. On the aniline ring at position 4 of the quinazoline moiety substituents like NO2, CN, CF3 led to very high BCRP inhibition potencies. The most potent compounds were further investigated for their intrinsic cytotoxicity and their ability to reverse the multidrug resistance. Compound 20, an anilinoquinazoline bearing a phenyl ring at position 2 and meta-nitro substitution on the 4-anilino ring, was found to have the highest therapeutic ratio. The most active compounds from each variation were also investigated for their effect on BCRP expression. It was found that compound 20 has no significant effect on BCRP expression, while compound 31 decreased the surface BCRP expression. The only difference in the two compounds was the presence of a 3,4-dimethoxyphenyl ring in compound 31 instead of phenyl substitution at position 2 of the quinazoline moiety. From the study of all target compounds, compound 20 was the most prominent compound having inhibitory potency even higher than Ko143, the most potent BCRP inhibitor known. Compound 20 was also found to be selective towards BCRP with a very high therapeutic ratio. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.10.007

文献信息

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

  公开号：US20080004297A1

  公开（公告）日：2008-01-03

  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.

  本发明涉及4-芳胺基喹唑啉及其类似物，其作为caspase激活剂和凋亡诱导剂具有有效性。本发明的化合物在治疗各种临床情况中有用，其中发生异常细胞的不受控制的生长和扩散。
• QUINAZOLINE DERIVATIVES FOR THE TREATMENT OF HERPESVIRAL INFECTIONS
  申请人：GPC Biotech AG

  公开号：EP1673346A1

  公开（公告）日：2006-06-28
• Quinazoline derivatives for the treatment of herpesviral infections
  申请人：Herget Thomas

  公开号：US20070123537A1

  公开（公告）日：2007-05-31

  The present invention relates to phenyl-quinazolinyl-amine derivatives and pharmaceutically acceptable salts thereof and pharmaceutical compositions comprising at least one of these derivatives and/or pharmaceutically salts thereof, as well as the use of these derivatives for the prophylaxis and/or treatment of herpesviral induced infections, including opportunistic infections, especially for the prophylaxis and/or treatment of infections and diseases induced by HCMV.
• US7989462B2
  申请人：——

  公开号：US7989462B2

  公开（公告）日：2011-08-02
• [EN] QUINAZOLINE DERIVATIVES FOR THE TREATMENT OF HERPESVIRAL INFECTIONS<br/>[FR] DERIVES DE QUINAZOLINE POUR LE TRAITEMENT D'INFECTIONS VIRALES HERPETIQUES
  申请人：AXXIMA PHARMACEUTICALS AG

  公开号：WO2005040125A1

  公开（公告）日：2005-05-06

  The present invention relates to phenyl-quinazolinyl-amine derivatives and pharmaceutically acceptable salts thereof and pharmaceutical compositions comprising at least one of these derivatives and/or pharmaceutically salts thereof, as well as the use of these derivatives for the prophylaxis and/or treatment of herpesviral induced infections, including opportunistic infections, especially for the prophylaxis and/or treatment of infections and diseases induced by HCMV.