CAS: 60233-66-1; 5-Chloro-3H-Quinazolin-4-One

上下游产品

CAS号2148-56-3 2-氨基-6-氯苯甲酸 | CAS号77287-34-4 甲亚胺酸 | CAS号7463-35-6 3-氯-2-甲基乙酰苯胺 | CAS号87-60-5 3-氯-2-甲基苯胺 | CAS号19407-42-2 2-乙酰氨基-6-氯-苯甲酸 | CAS号400784-50-1 5-氯-8-硝基喹唑啉-4-醇

📜3-氯-2-甲基苯胺置于盐酸,Potassium Permanganate,Magnesium Sulfate体系中,用 二氯甲烷,水 作为反应溶剂,化学反应 8.5H,反应生成 5-氯-4(3H)-喹唑啉酮
参考文献:Synthesis And Antitumor Evaluation Of Novel 5-Substituted-4-Hydroxy-8-Nitroquinazolines As Egfr Signaling-Targeted Inhibitors
标题:Synthesis And Antitumor Evaluation Of Novel 5-Substituted-4-Hydroxy-8-Nitroquinazolines As Egfr Signaling-Targeted Inhibitors
摘要:The Synthesis And Biological Activity Of A Series Of Novel 5-Substituted-4-Hydroxy-8-Nitroquinazolines That May Function As Inhibitors Of Egfr-And/or Erbb-2-Related Oncogenic Signaling Are Described. These Compounds Were Prepared By Snar Reaction Of 5-Chloro-4-Hydroxy-8-Nitroquinazo Line With Alkyl Or Aryl Amines,Or Alkyl Alcohol As Nucleophiles. Although The Enzyme Assay Showed A Weak Inhibition Effect Against Both Egfr And Erbb-2 Tyrosine Kinases,The Cell-Based Antitumor Activity Turned Out Promising. Compounds Having 5-Anilino Substituent Exhibit High Potency With 5-(4-Methoxy)Anilino-4-Hydroxy-8-Nitroquinazoline (1H) Being The Best Dual Egfr/erbb-2 Inhibitors,Which Effectively Inhibited The Growth Of Both Egfr (Mda-Mb-468,Ic50 < 0-01 Mu M) And Erbb-2 (Sk-Br-3,Ic50 = 13 Mu M) Overexpressing Human Tumor Cell Lines In Vitro. More Interestingly,The Variation Of The Substituent(S) At The 3-And/or 4-Position Of The 5-Anilino Portion Was Found To Modulate The Selectivity And Potency Dramatically. However,Compounds Having An Alkylamino Or Alkyloxy Group At The 5-Position Of 4-Hydroxy-8-Nitroquinazolines Are Essentially Inactive. These Results Are Consistent With Molecular Modeling Observations. This Study Was The First Attempt To Identify New Structural Types Of Dual Egfr/erbb-2-Related Signaling Inhibitors By Incorporation Of The Anilino Group At The 5-Position Of 4-Hydroxy-8-Nitroquinazolines' Core Structure,Providing Promising New Templates For Further Development Of Potent Inhibitors Targeting Both Egfr And Erbb-2 Tyrosine Kinases. (C) 2005 Elsevier Ltd. All Rights Reserved.
DOI:10.1016/j.Bmc.2005.05.045

专利信息

专利号:US-2625549-A
优先权日:1951-03-17
标 题 :Synthesis of 3-[beta-keto-gamma-(2-piperidyl) propyl]-4-quinazolone compounds
发明人：BAKER BERNARD R; QUERRY MERLE V
权利人:AMERICAN CYANAMID CO