1-(3-((6,7-dimethoxyquinazolin-4-yl)amino)phenyl)ethanone | 153437-66-2

• 分子结构分类: 有机化合物
• 英文名称: 1-(3-((6,7-dimethoxyquinazolin-4-yl)amino)phenyl)ethanone
• 英文别名: 1-{3-[(6,7-Dimethoxyquinazolin-4-yl)amino]phenyl}ethanone；1-[3-[(6,7-dimethoxyquinazolin-4-yl)amino]phenyl]ethanone
• CAS: 153437-66-2
• 化学式: C₁₈H₁₇N₃O₃
• 分子量: 323.351
• InChiKey: OMRVBDOHGDQYFB-UHFFFAOYSA-N

物化性质

• 沸点：
  497.8±45.0 °C(Predicted)
• 密度：
  1.265±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  73.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3,4-二甲氧基苯甲醛 、 1-(3-((6,7-dimethoxyquinazolin-4-yl)amino)phenyl)ethanone 在 lithium hydroxide 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以30%的产率得到(E)-3-(3,4-dimethoxyphenyl)-1-(3-((6,7-dimethoxyquinazolin-4-yl)amino)phenyl) prop-2-en-1-one
  参考文献：
  名称：

  The combination of quinazoline and chalcone moieties leads to novel potent heterodimeric modulators of breast cancer resistance protein (BCRP/ABCG2)

  摘要：

  During the last decade it has been found that chalcones and quinazolines are promising inhibitors of ABCG2. The combination of these two scaffolds offers a new class of heterocyclic compounds with potentially high inhibitory activity against ABCG2. For this purpose we investigated 22 different heterodimeric derivatives. In this series only methoxy groups were used as substituents as these had been proven superior for inhibitory activity of chalcones. All compounds were tested for their inhibitory activity, specificity and cytotoxicity. The most potent ABCG2 inhibitor in this series showed an IC50 value of 0.19 mu M. It possesses low cytotoxicity (GI(50) = 93 mu M), the ability to reverse MDR and is nearly selective toward ABCG2. Most compounds containing dimethoxy groups showed slight activity against ABCB1 too. Among these three compounds (17,19 and 24) showed even higher activity toward ABCB1 than ABCG2. All inhibitors were further screened for their effect on basal ATPase activity. Although the basal ATPase activity was partially stimulated, the compounds were not transported by ABCG2. Thus, quinazoline-chalcones are a new class of effective ABCG2 inhibitors. (C) 2016 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2016.03.067
• 作为产物：
  描述：

  6,7-二甲氧基喹唑啉-4-酮 在 三氯氧磷 作用下， 以 异丙醇 为溶剂， 反应 9.0h， 生成 1-(3-((6,7-dimethoxyquinazolin-4-yl)amino)phenyl)ethanone
  参考文献：
  名称：

  The combination of quinazoline and chalcone moieties leads to novel potent heterodimeric modulators of breast cancer resistance protein (BCRP/ABCG2)

  摘要：

  During the last decade it has been found that chalcones and quinazolines are promising inhibitors of ABCG2. The combination of these two scaffolds offers a new class of heterocyclic compounds with potentially high inhibitory activity against ABCG2. For this purpose we investigated 22 different heterodimeric derivatives. In this series only methoxy groups were used as substituents as these had been proven superior for inhibitory activity of chalcones. All compounds were tested for their inhibitory activity, specificity and cytotoxicity. The most potent ABCG2 inhibitor in this series showed an IC50 value of 0.19 mu M. It possesses low cytotoxicity (GI(50) = 93 mu M), the ability to reverse MDR and is nearly selective toward ABCG2. Most compounds containing dimethoxy groups showed slight activity against ABCB1 too. Among these three compounds (17,19 and 24) showed even higher activity toward ABCB1 than ABCG2. All inhibitors were further screened for their effect on basal ATPase activity. Although the basal ATPase activity was partially stimulated, the compounds were not transported by ABCG2. Thus, quinazoline-chalcones are a new class of effective ABCG2 inhibitors. (C) 2016 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2016.03.067

文献信息

• 4-Anilinequinazolines with adenosine-kiase inhibitor properties
  申请人：Franchini Gomes Kleber

  公开号：US20070060600A1

  公开（公告）日：2007-03-15

  The present invention relates to the use of 4-anilinoquinazoline derivatives as adenosine-kinase inhibitors. The present invention also relates to a method for protecting tissues and organs like heart, brain and kidneys affected by ischemia, and for treating heart insufficiency, myocardium infarct, arrhythmia, arterial hypertension, atherosclerosis, coronary artery restenosis after angioplasty, chronic renal insufficiency, cerebral vascular accident, and chronic inflanunatory diseases (e.g., rheumatoid arthritis). The present invention also relates to the compound 6,7-dimethoxy-4-(3′-N′,N′-dimethylaminoanilino)quinazoline, or a pharmaceutically acceptable salt thereof, pharmaceutical composition comprising it and use of such compound in the manufacture of a medicament for treating or preventing diseases or conditions that are benefited from the adenosine-kinase inhibition.

  本发明涉及使用4-苯胺基喹唑啉衍生物作为腺苷激酶抑制剂。本发明还涉及一种保护受缺血影响的心脏、脑和肾等组织和器官，并治疗心力衰竭、心肌梗塞、心律失常、动脉高血压、动脉粥样硬化、血管成形术后冠状动脉再狭窄、慢性肾功能不全、脑血管意外和慢性炎症性疾病（如类风湿性关节炎）的方法。本发明还涉及化合物6,7-二甲氧基-4-(3'-N',N'-二甲基氨基苯基)喹唑啉或其药学上可接受的盐、包含它的制药组合物以及使用该化合物制造治疗或预防从腺苷激酶抑制中受益的疾病或病情的药物的用途。
• 4-ANILINOQUINAZOLINE DERIVATIVES WITH ADENOSINE-KINASE INHIBITORY PROPERTIES
  申请人：UNIVERSIDADE ESTADUAL DE CAMPINAS - UNICAMP

  公开号：EP1737832B1

  公开（公告）日：2011-12-14
• US8513267B2
  申请人：——

  公开号：US8513267B2

  公开（公告）日：2013-08-20