4141-08-6Relevant academic research and scientific papers
Discovery and antitumor activity of Benzo[d]imidazol-containing 2,4-diarylaminopyrimidine analogues as ALK inhibitors with mutation-combating effects
Li, Zheng,Guo, Ming,Cao, Meng,Zhao, Tianming,Li, Mingzhu,Zhai, Xin
, (2021/03/26)
To address drug resistance caused by ALK kinase mutations, a series of novel 2,4-diarylaminopyrimidine (DAAP) analogues were designed by incorporating 1H-benzo[d]imidazol motif onto the maternal framework. All compounds were efficiently synthesized and an
Fungal Dioxygenase AsqJ Is Promiscuous and Bimodal: Substrate-Directed Formation of Quinolones versus Quinazolinones
Einsiedler, Manuel,Jamieson, Cooper S.,Maskeri, Mark A.,Houk, Kendall N.,Gulder, Tobias A. M.
supporting information, p. 8297 - 8302 (2021/03/01)
Previous studies showed that the FeII/α-ketoglutarate dependent dioxygenase AsqJ induces a skeletal rearrangement in viridicatin biosynthesis in Aspergillus nidulans, generating a quinolone scaffold from benzo[1,4]diazepine-2,5-dione substrates. We report that AsqJ catalyzes an additional, entirely different reaction, simply by a change in substituent in the benzodiazepinedione substrate. This new mechanism is established by substrate screening, application of functional probes, and computational analysis. AsqJ excises H2CO from the heterocyclic ring structure of suitable benzo[1,4]diazepine-2,5-dione substrates to generate quinazolinones. This novel AsqJ catalysis pathway is governed by a single substituent within the complex substrate. This unique substrate-directed reactivity of AsqJ enables the targeted biocatalytic generation of either quinolones or quinazolinones, two alkaloid frameworks of exceptional biomedical relevance.
Design, synthesis, biological activities and 3D-QSAR studies of quinazolinone derivatives containing hydrazone structural units
Shao, Li-Hui,Fan, Si-Li,Meng, Ying-Fen,Gan, Yi-Yuan,Shao, Wu-Bin,Wang, Zhen-Chao,Chen, Dan-Ping,Ouyang, Gui-Ping
, p. 4626 - 4631 (2021/03/22)
In this study, three series of quinazolinone derivatives containing hydrazone structures were designed and synthesized. Bioactivity assays indicated that these compounds showed good antitumour activities towards human lung cancer cells (A549) and human pr
Palladium-catalyzed synthesis of novel trifluoromethylated quinazolinone, N-arylquinazoline and N-benzylquinazoline derivatives
Sajadi, Mahdieh Sadat,Kazemi, Elham,Darehkordi, Ali
supporting information, (2021/04/23)
A simple and palladium-catalyzed procedure for synthesis of a novel series of potentially biologically active trifluoromethyl-substituted quinazolinones and N-arylquinazoline derivatives via condensation-cyclization reaction of 2-aminobenzamide, 2-amino-N′-arylbenzimidamides and 2-amino-N′-benzylbenzimidamides with trifluoroacetimidoyl chlorides has been developed. noteworthy, this investigation showed the possible of transition-metal-catalyzed activation of trifluoroacetimidoyl chlorides as a carbon trifluoromethylated source for the synthesis of quinazolines and quinazolinone derivatives in good to excellent yields.
Electrochemical utilization of methanol and methanol-d4 as a C1 source to access (deuterated) 2,3-dihydroquinazolin-4(1H)-one
Liu, Mingzhu,Wei, Yu,Xu, Liang
supporting information, (2021/10/06)
Herein, an electrocatalytic protocol for the synthesis of 2,3-dihydroquinazolin-4(1H)-one has been disclosed. Methanol is activated and utilized as the C1 source to cyclize with 2-aminobenzamides. This cyclization reaction proceeds conveniently (room temperature and air atmosphere) without any homogeneous metal catalysts, external oxidants, or bases. A wide variety of N,N-disubstituted 2,3-dihydroquinazolin-4(1H)-ones are obtained via this approach. Moreover, when methanol-d4 is used, a deuterated methylene motif is incorporated into the N-heterocycles, providing an efficient approach to the deuterated N-heterocycles.
Direct synthesis of quinazolinones via the carbon-supported acid-catalyzed cascade reaction of isatoic anhydrides with amides and aldehydes
Zhang, Xiangyu,Luo, Chujun,Chen, Xiaoyong,Ma, Weilin,Li, Bin,Lin, Zirui,Chen, Xiuwen,Li, Yibiao,Xie, Feng
, (2021/02/20)
A novel catalytic system is reported for the construction of quinazolinones via the carbon-supported acid-catalyzed cascade coupling of isatoic anhydrides with amides and aldehydes. Subsequent selective hydrosilylation of the quinazolinones using a hydrogen-transfer strategy was also explored to provide dihydroquinazolines with structural diversity. The developed methodology proceeds with a broad substrate scope, excellent functional group tolerance, and utilizes a reusable catalyst and air as a green oxidant.
Green synthesis of novel phosphonate derivatives using ultrasonic irradiation
Sharafian, Shirin,Hossaini, Zinatossadat,Rostami-Charati, Faramarz,Khalilzadeh, Mohammad A.
, p. 1283 - 1291 (2020/11/19)
[Figure not available: see fulltext.] A novel and efficient procedure for the generation of quinazolinone phosphonate derivatives employing the reaction of euparin, isatin or its derivatives, primary amines, dialkyl acetylenedicarboxylates, trimethyl phosphite or triphenyl phosphite, and acidic solution of hydrogen peroxide in aqueous media at ambient temperature under ultrasonic irradiation was developed. Without ultrasonic irradiation, the reaction does not proceed and agitation of the reaction mixture is difficult. Some advantages of this procedure are: short time of reaction, high yields of products, easy isolation of products.
Quinazolinone compound containing hydrazone structural unit or stereoisomer, salt or solvate of the quinazolinone compound
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Paragraph 0041-0043, (2020/07/08)
The invention relates to a quinazolinone compound containing a hydrazone structural unit, or a stereoisomer, or a salt or a solvate of the quinazolinone compound. The compound has a structure as shownin a general formula (I) shown in the specification. Th
Design, synthesis and in vitro biological evaluation of quinazolinone derivatives as EGFR inhibitors for antitumor treatment
Fu, Yihong,Gan, Yiyuan,Le, Yi,Li, Wen,Liu, Jiamin,Ouyang, Guiping,Wang, Zhenchao,Yan, Longjia,Zhou, Zhixu,Zou, Xue
, p. 555 - 564 (2020/02/11)
In this paper, a series of novel 3-methyl-quinazolinone derivatives was designed, synthesised and evaluated for antitumor activity in vitro on wild type epidermal growth factor receptor tyrosine kinase (EGFRwt-TK) and three human cancer cell li
Pyrroformyl-containing 2,4-diaminopyrimidine derivatives as a new optimization strategy of ALK inhibitors combating mutations
Cao, Meng,Chen, Yuxiang,Guo, Ming,Wei, Shangfei,Zhai, Xin,Zhao, Tianming
, (2020/09/01)
Aiming to identify new optimization strategy effective for ALK-mutations, two series of pyrroformyl-containing 2,4-diaminopyrimidine compounds (11a-o, 12a-o) were designed, synthesized and evaluated for their anti-proliferative activities against three ca
