- Method for preparing quinazolone and derivatives thereof by using chitosan-loaded copper catalyst
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The invention discloses a method for preparing quinazolone and derivatives thereof by using a chitosan-loaded copper catalyst, which comprises the following steps of replacing residual gas in a reaction container with inert gas, adding a catalytic amount of copper ion-loaded chitosan catalyst, substituted 2-halogenated benzoic acid, substituted amidine hydrochloride, inorganic alkali and a mixed solvent into the reaction container, and heating for reaction, after the reaction time is 2-18 hours, extracting the product by using ethyl acetate, filtering and recovering the copper ion-loaded chitosan catalyst, concentrating the filtrate under reduced pressure, and purifying the product by column chromatography. The method has the advantages of low catalyst dosage, recoverability, easy separation after reaction, no metal residue, simple post-treatment, and suitableness for large-scale production.
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Paragraph 0108-0114
(2021/05/12)
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- Design, Synthesis, and Structure-Activity Relationship of Quinazolinone Derivatives as Potential Fungicides
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Plant diseases caused by phytopathogenic fungi reduce the yield and quality of crops. To develop novel antifungal agents, we designed and synthesized eight series of quinazolinone derivatives and evaluated their anti-phytopathogenic fungal activity. The bioassay results revealed that compounds KZL-15, KZL-22, 5b, 6b, 6c, 8e, and 8f exhibited remarkable antifungal activity in vitro. Especially, compound 6c displayed the highest bioactivity against Sclerotinia sclerotiorum, Pellicularia sasakii, Fusarium graminearum, and Fusarium oxysporum, displaying appreciable IC50 values (50% inhibitory concentration) of 2.46, 2.94, 6.03, and 11.9 μg/mL, respectively. A further mechanism interrogation revealed abnormal mycelia, damaged organelles, and changed permeability of cell membranes in S. sclerotiorum treated with compound 6c. In addition, the in vivo bioassay indicated that compound 6c possessed comparable curative and protective effects (87.3 and 90.7%, respectively) to the positive control azoxystrobin (89.5 and 91.2%, respectively) at 100 μg/mL concentration against S. sclerotiorum. This work validated the potential of compound 6c as a new and promising fungicide candidate, contributing to the exploration of potent antifungal agents.
- Peng, Jing-Wen,Yin, Xiao-Dan,Li, Hu,Ma, Kun-Yuan,Zhang, Zhi-Jun,Zhou, Rui,Wang, Yu-Ling,Hu, Guan-Fang,Liu, Ying-Qian
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p. 4604 - 4614
(2021/05/06)
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- Discovery and development of extreme selective inhibitors of the ITD and D835Y mutant FLT3 kinases
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Aberrant activation of FMS-like tyrosine receptor kinase 3 (FLT3) is implicated in the pathogenesis of acute myeloid leukemia (AML) in 20–30% of patients. In this study we identified a highly selective (phenylethenyl)quinazoline compound family as novel potent inhibitors of the FLT3-ITD and FLT3-D835Y kinases. Their prominent effects were confirmed by biochemical and cellular proliferation assays followed by mice xenograft studies. Our modelling experiments and the chemical structures of the compounds predict the possibility of covalent inhibition. The most effective compounds triggered apoptosis in FLT3-ITD AML cells but had either weak or no effect in FLT3-independent leukemic and non-leukemic cell lines. Our results strongly suggest that our compounds may become therapeutics in relapsing and refractory AML disease harboring various ITD and tyrosine kinase domain mutations, by their ability to overcome drug resistance.
- Baska, Ferenc,Sipos, Anna,?rfi, Zoltán,Nemes, Zoltán,Dobos, Judit,Szántai-Kis, Csaba,Szabó, Eszter,Szénási, Gábor,Dézsi, László,Hamar, Péter,Cserepes, Mihály T.,Tóvári, József,Garamv?lgyi, Rita,Krekó, Marcell,?rfi, László
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- Quinazolinone compounds and application in preparing drug for preventing agricultural plant diseases
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The invention discloses application of quinazolinone compounds KZL-01-KZL-34 in preventing or resisting agricultural plant fungal diseases. Antimicrobial activity testing results show that the compounds have inhibition activity on the plant fungal diseases caused by sclerotinia sclerotiorum, rhizoctonia solani, fusarium graminearum Sehw. and botrytis cinerea, and especially have higher inhibitionactivity on the rhizoctonia solani, the inhibition activity of part of the compounds on the germs is higher than that of azoxystrobin, and the quinazolinone compounds can be used as lead compounds ofan agricultural fungicide to be developed.
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Paragraph 0020-0024; 0029-0032
(2019/11/25)
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- STYRYL QUINAZOLINE DERIVATIVES AS PHARMACEUTICALLY ACTIVE AGENTS
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The present invention relates to styryl quinazoline derivatives of the general formula (I) and pharmaceutically acceptable solvates, hydrates, salts, regioisomeric and polymorphic forms thereof as well as pharmaceutical compositions containing at least on
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Page/Page column 8
(2015/02/25)
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- A convenient aqueous copper-catalyzed synthesis of quinazolinones
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A simple and highly efficient method for the aqueous copper-catalyzed coupling reactions with the aid of a commercially available surfactant (TPGS-750-M) is reported. In an aqueous micellar medium, 2-halobenzoic acids derivatives reacted with amidines and guanidines and generated the corresponding quinazolinone derivatives in good to excellent yields in the range of room temperature to, at most, 50°C. In addition, the reaction medium can be recycled, and this method led to a significant improvement of the E factors in comparison with the previously reported process.
- Xu, Yulong,Xie, Qiong,Li, Wei,Sun, Hongpeng,Wang, Yonghui,Shao, Liming
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supporting information
p. 4853 - 4858
(2015/07/27)
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- Dicopper complexes catalyzed coupling/cyclization of 2-bromobenzoic acids with amidines leading to quinazolinones
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Dicopper(I) complexes {Cu2(bpnp)(CH3CN) 4}(PF6)2] (2), [{Cu2(bpnp)(CH 3CN)4}(BAr4F)2] (3) and [Cu2(bpnp)Cl2] (4) were prepared from the complexation of [Cu(CH3CN)4](PF6) with 2,7-bis(2-pyridyl)-1,8- naphthyridine (bpnp) followed by anion metathesis and treatment of chloride sequentially. The X-ray structural analysis of 4 indicates the molecule to have a twofold axis passing through the Cu2Cl2 core, which has the shape of a butterfly, and that the Cu atom is tetrahedrally coordinated with in a Cl2N2 donor set. In preliminary experiments 2 was found to be an effective catalyst in the coupling/cyclization of 2-bromobenzoic acids with amidines, providing the corresponding quinazolinones in good yields. Copyright
- Hung, Ming-Uei,Liao, Bei-Sih,Liu, Yi-Hong,Peng, Shie-Ming,Liu, Shiuh-Tzung
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p. 661 - 665
(2014/09/30)
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- Fe3O4 nanoparticle-supported copper(I): Magnetically recoverable and reusable catalyst for the synthesis of quinazolinones and bicyclic pyrimidinones
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A highly efficient, easily recoverable and reusable Fe3O 4 magnetic nanoparticle-supported Cu(I) catalyst has been developed for the synthesis of quinazolinones and bicyclic pyrimidinones. In the presence of supported Cu(I) catalyst (10 mol%), amidines reacted with substituted 2-halobenzoic acids and 2-bromocycloalk-1-enecarboxylic acids to generate the corresponding N-heterocycle products in good to excellent yields at room temperature in DMF. In addition, the supported Cu(I) catalyst could be recovered at least 10 times without significant loss of its catalytic activity. Copyright
- Yu, Lin,Wang, Min,Li, Pinhua,Wang, Lei
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p. 576 - 582,7
(2020/09/02)
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- HALOGENATED QUINAZOLINYL NITROFURANS AS ANTIBACTERIAL AGENTS
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The present invention includes novel compounds of the formula (I) wherein X is absent or trans or cis CHCH, R1 is (C1-C10) alkyl unsubstituted or substituted by one to three hydroxy, (C1-C10) alkenyl unsubstituted or substituted by one to three hydroxy, (C1-C10) alkynyl unsubstituted or substituted by one to three hydroxy, or aryl unsubstituted or substituted by one to three hydroxy; R2 is hydrogen, alkyl or aryl; R3 and R4 are, independently of each other, H, halogen, or a solubilizing group, with the proviso that at least one of R3 and R4 is halogen; and pharmaceutically acceptable salts thereof. The invention also includes pharmaceutically acceptable formulations of said compounds which exhibit antibiotic activity against a wide spectrum of microorganisms including organisms which are resistant to multiple antibiotic families and are useful as antibacterial agents for treatment or prophylaxis of bacterial infections, or their use as antiseptics, agents for sterilization or disinfection.
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Page/Page column 17
(2008/06/13)
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