1022-44-2Relevant articles and documents
Isoquinoline and quinazoline urea analogues as antagonists for the human-adenosine A3 receptor
Van Muijlwijk-Koezen, Jacqueline E.,Timmerman, Henk,Van Der Goot, Henk,Menge, Wiro M. P. B.,Von Drabbe Künzel, Jacobien Frijtag,De Groote, Miriam,Ijzerman, Adriaan P.
, p. 2227 - 2238 (2000)
Isoquinoline and quinazoline urea derivatives were found to bind to human adenosine AS receptors. Series of N-phenyl-N'-quinazolin-4-ylurea derivatives and N-phenyl-N'-isoquinolin-1-ylurea derivatives were synthesized and tested in radioligand binding ass
Efficient three-component synthesis of 4-aminoquinazolines
Heravi, Majid M.,Sadjadi, Samaheh,Haj, Negar Mokhtari,Oskooie, Hossein A.,Bamoharram, Fatemeh F.
, p. 861 - 867 (2010)
4-Aminoquinazolines were synthesized in good yields via a one-pot, three-component reaction of anthranilonitrile, acylchlorides, and ammonium acetate in the presence of catalytic amounts silica-supported Preyssler nanoparticles under refluxing conditions.
Synthesis and biological evaluation of quinazoline derivatives – A SAR study of novel inhibitors of ABCG2
Krapf, Michael K.,Gallus, Jennifer,Spindler, Anna,Wiese, Michael
, p. 506 - 525 (2018/11/06)
Multidrug resistance (MDR) is a major obstacle for effective chemotherapeutic treatment of cancer frequently leading to failure of the therapy. MDR is often associated with the overexpression of ABC transport proteins like ABCB1 or ABCG2 which efflux harmful substances out of cells at the cost of ATP hydrolysis. One way to overcome MDR is to apply potent inhibitors of ABC transporters to restore the sensitivity of the cells toward cytostatic agents. This study focusses on the synthesis and evaluation of novel 2,4-disubstituted quinazoline derivatives regarding the structure-activity-relationship (SAR), their ability to reverse MDR and their mode of interaction with ABCG2. Hence, the inhibitory potency and selectivity toward ABCG2 was determined. Moreover, the intrinsic cytotoxicity and the reversal of MDR were investigated. Interaction type studies with the substrate Hoechst 33342 and conformational analyses of ABCG2 with 5D3 monoclonal antibody were performed for a better understanding of the underlying mechanisms. In our study we could further enhance the inhibitory effect against ABCG2 (compound 31, IC50: 55 nM) and identify the structural features that are crucial for inhibitory potency, the impact on transport activity and binding to the protein.
Efficient synthesis of 2-arylquinazolin-4-amines via a copper-catalyzed diazidation and ring expansion cascade of 2-arylindoles
Xu, Meng-Meng,Cao, Wen-Bin,Xu, Xiao-Ping,Ji, Shun-Jun
supporting information, p. 12602 - 12605 (2018/11/20)
Copper-catalyzed synthesis of 2-arylquinazolin-4-amines from readily available 2-arylindoles and TMSN3 has been developed. The mechanism study shows that the domino reaction may involve a free radical diazidation, denitrogenation, intramolecular cyclization and ring expansion sequence.
A Highly Efficient Copper-Catalyzed Three-Component Synthesis of 4-Aminoquinazolines
Yang, Lei,Luo, Honghua,Sun, Yan,Shi, Zhenyu,Ni, Kaidong,Li, Fei,Chen, Dongyin
, p. 2535 - 2535 (2017/05/22)
A highly efficient copper-catalyzed one-pot protocol is developed for the synthesis of 4-aminoquinazolines from easily available 2-iodo- or 2-bromobenzimidamides, aldehydes, and sodium azide. This one-pot approach proceeds via consecutive copper-catalyzed SNAr substitution, reduction, cyclization, oxidation and tautomerization. The corresponding target products (26 examples) are obtained in 50-90% yield.
