- 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 0053-0059
(2021/05/12)
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- Cp?CoIII-catalyzed formal [4+2] cycloaddition of benzamides to afford quinazolinone derivatives
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A Cp?CoIII-catalyzed arene C-H bond amidation/annulation of benzamides was developed to afford quinazolinone derivatives in one-pot with high yields and broad substrate scope. This method could be applied to the synthesis of quinazolinone drugs and late-stage modification of natural products.
- Yang, Jingshu,Hu, Xiao,Liu, Zijie,Li, Xueyuan,Dong, Yi,Liu, Gang
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supporting information
p. 13840 - 13843
(2019/11/21)
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- One-pot synthesis of quinazolin-4(3H)-ones and 2,3-dihydroquinazolin-4(1H)-ones utilizing N-(2-aminobenzoyl)benzotriazoles
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A convenient and efficient method has emerged for the one-pot synthesis of substituted quinazolin-4(3H)ones and nonaromatic alkaloids. 2-Substituted quinazolin-4(3H)-ones, 2,3-disubstituted quinazolin-4(3H)-ones, and 2,3-dihydroquinazolin-4(1H)-ones were obtained at yields of 46% to 95% by a one-pot reaction of N-(2-aminobenzoyl) benzotriazoles with amines and orthoesters or aldehydes under catalyst-free conditions.
- ?enol, ?lbilge Merve,?elik, ?lhami,Avan, ?lker
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p. 1580 - 1596
(2020/01/03)
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- Quinazolin-4(3H)-one-Based Hydroxamic Acids: Design, Synthesis and Evaluation of Histone Deacetylase Inhibitory Effects and Cytotoxicity
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The present article describes the synthesis and biological activity of various series of novel hydroxamic acids incorporating quinazolin-4(3H)-ones as novel small molecules targeting histone deacetylases. Biological evaluation showed that these hydroxamic acids were potently cytotoxic against three human cancer cell lines (SW620, colon; PC-3, prostate; NCI?H23, lung). Most compounds displayed superior cytotoxicity than SAHA (suberoylanilide hydroxamic acid, Vorinostat) in term of cytotoxicity. Especially, N-hydroxy-7-(7-methyl-4-oxoquinazolin-3(4H)-yl)heptanamide (5b) and N-hydroxy-7-(6-methyl-4-oxoquinazolin-3(4H)-yl)heptanamide (5c) (IC50 values, 0.10–0.16 μm) were found to be approximately 30-fold more cytotoxic than SAHA (IC50 values of 3.29–3.67 μm). N-Hydroxy-7-(4-oxoquinazolin-3(4H)-yl)heptanamide (5a; IC50 values of 0.21–0.38 μm) was approximately 10- to 15-fold more potent than SAHA in cytotoxicity assay. These compounds also showed comparable HDAC inhibition potency with IC50 values in sub-micromolar ranges. Molecular docking experiments indicated that most compounds, as represented by 5b and 5c, strictly bound to HDAC2 at the active binding site with binding affinities much higher than that of SAHA.
- Hieu, Doan Thanh,Anh, Duong Tien,Hai, Pham-The,Thuan, Nguyen Thi,Huong, Le-Thi-Thu,Park, Eun Jae,Young Ji,Soon Kang, Jong,Phuong Dung, Phan Thi,Han, Sang-Bae,Nam, Nguyen-Hai
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- ANTIBIOTICS EFFECTIVE FOR GRAM-NEGATIVE PATHOGENS
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Disclosed herein are antibacterial compounds that accumulate in Gram-negative bacteria, methods of preparing the compounds, and methods of using the compounds to inhibit or kill microbes, and methods of treating microbial infections, such as Gram-negative
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Page/Page column 83; 84-85; 87
(2019/10/04)
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- Novel Hydroxamic Acid Incorporating Quinazolin-4(3H)-ones as Histone Deacetylase Inhibitors and Anticancer Composition Comprising the Same
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The compound according HDAC(histone deacetylase) to the present -4(3H)- won invention can, be used as an active. ingredient of, a potent anticancer agent, HDAC since the compound according, to the present invention can be used. as, an active ingredient of a potent anticancer agent, since the compound. according to the present invention can be used as an active ingredient of a potent anticancer agent. (by machine translation)
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Paragraph 0103; 0144-0145
(2020/03/03)
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- Folic-acid antagonist for treating intestinal bacterial infection, preparation and application thereof
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The invention relates to a folic-acid antagonist for treating intestinal bacterial infection, preparation and an application thereof. The folic-acid antagonist is a compound as shown in Formula I or asalt of the compound as shown in Formula I (the Formula
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Paragraph 0030; 0035; 0039; 0040; 0041; 0042
(2019/04/27)
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- Synthesis, Cytotoxic, and Antibacterial Evaluation of Quinazolinone Derivatives with Substituted Amino Moiety
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A series of novel quinazolinone derivatives containing a substituted amino moiety were synthesized, evaluated for their cytotoxic and antibacterial activities. The results of MTT assay showed that all synthesized target compounds 5A?–?5O showed potent cytotoxicity against SGC-7901 (IC50, 0.72?–?1.41?μm). Moreover, the compounds 5D, 5I, and 5K showed better selectivity as compared with positive controls pemetrexed and MTX due to weak cytotoxicity against normal tissue cell line HUVSMC. Among synthesized compounds, the compounds 5E, 5J, 5L, and 5N showed broad-spectrum cytotoxic activities against at least four cancer cell lines at a micromolar level. The results of antibacteria evaluation revealed that all synthesized compounds showed good to moderate antibacterial activities against Gram-negative bacteria Escherichia coli. Among them, the MIC values of the compounds 5C, 5F, and 5M were 0.31?μg/mL.
- Zhan, Xiaoping,Xu, Yun,Qi, Qi,Wang, Yaolin,Shi, Huiying,Mao, Zhenmin
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- A Comparative Investigation: Group 9 Cp?M(III)-Catalyzed Formal [4 + 2] Cycloaddition as an Atom-Economic Approach to Quinazolines
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A comparative study on the catalytic activity of different group 9 [Cp?M(III)] complexes in the formal [4 + 2] cycloaddition of arenes with rarely explored free imines and dioxazolones for the construction of multisubstituted quinazolines is reported herein. This investigation revealed that the cobalt catalyst is uniquely suited to this transformation due to its strong Lewis acidity and high sensitivity to steric hindrance.
- Wang, Xiaoming,Lerchen, Andreas,Glorius, Frank
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supporting information
p. 2090 - 2093
(2016/06/01)
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- Synthesis and evaluation of quinazolines as inhibitors of the bacterial cell division protein FtsZ
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The bacterial cell division protein FtsZ is one of many potential targets for the development of novel antibiotics. Recently, zantrin Z3 was shown to be a cross-species inhibitor of FtsZ; however, its specific interactions with the protein are still unknown. Herein we report the synthesis of analogues that contain a more tractable core structure and an analogue with single-digit micromolar inhibition of FtsZs GTPase activity, which represents the most potent inhibitor of Escherichia coli FtsZ reported to date. In addition, the zantrin Z3 core has been converted to two potential photo-cross-linking reagents for proteomic studies that could shed light on the molecular interactions between FtsZ and molecules related to zantrin Z3.
- Nepomuceno, Gabriella M.,Chan, Katie M.,Huynh, Valerie,Martin, Kevin S.,Moore, Jared T.,Obrien, Terrence E.,Pollo, Luiz A. E.,Sarabia, Francisco J.,Tadeus, Clarissa,Yao, Zi,Anderson, David E.,Ames, James B.,Shaw, Jared T.
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supporting information
p. 308 - 312
(2015/03/30)
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- Metal- and Oxidant-Free Synthesis of Quinazolinones from β-Ketoesters with o-Aminobenzamides via Phosphorous Acid-Catalyzed Cyclocondensation and Selective C-C Bond Cleavage
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A general and efficient phosphorous acid-catalyzed cyclocondensation of β-ketoesters with o-aminobenzamides via selective C-C bond cleavage leading to quinazolinones is developed. This reaction proceeds smoothly under metal- and oxidant-free conditions, giving both 2-alkyl- and 2-aryl-substituted quinazolinones in excellent yields. This strategy can also be applied to the synthesis of other N-heterocycles, such as benzimidazoles and benzothiazoles.
- Li, Zhongwen,Dong, Jianyu,Chen, Xiuling,Li, Qiang,Zhou, Yongbo,Yin, Shuang-Feng
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p. 9392 - 9400
(2015/10/12)
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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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- QUINAZOLINE DERIVATIVES AS PDE10A ENZYME INHIBITORS
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This invention is directed to compounds, which are PDE10A enzyme inhibitors. The invention provides a pharmaceutical composition comprising a therapeutically effective amount of a compound of the invention and a pharmaceutically acceptable carrier. The pr
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Page/Page column 58; 59
(2013/04/24)
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- Catalyst/ligand-free synthesis of benzimidazoles and quinazolinones from amidines via intramolecular transamination reaction
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An efficient catalyst/ligand-free synthesis of benzimidazoles and quinazolinones from amidines in quantitative yields has been described.
- Gupta, Sahaj,Agarwal, Piyush K.,Kundu, Bijoy
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experimental part
p. 1887 - 1890
(2010/09/07)
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- Discovery and structure-activity relationships of 4-aminoquinazoline derivatives, a novel class of opioid receptor like-1 (ORL1) antagonists
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Synthesis and structure-activity relationship studies of a series of 4-aminoquinazoline derivatives led to the identification of (1R,2S)-17, N-[(1R,2S)-2-({2-[(4-chlorophenyl)carbonyl]amino-6-methylquinazolin-4-yl}amino)cyclohexyl]guanidine dihydrochloride, as a highly potent ORL1 antagonist with up to 3000-fold selectivity over the μ, δ, and κ opioid receptors. Molecular modeling clarified the structural factors contributing to the high affinity and selectivity of (1R,2S)-17.
- Okano, Masahiko,Mito, Jun,Maruyama, Yasufumi,Masuda, Hirofumi,Niwa, Tomoko,Nakagawa, Shin-ichiro,Nakamura, Yoshitaka,Matsuura, Akira
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experimental part
p. 119 - 132
(2011/02/25)
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- Microwave-assisted synthesis of quinazolinone derivatives by efficient and rapid iron-catalyzed cyclization in water
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A green, rapid, and efficient method was developed for synthesizing quinazolinone derivatives from substituted 2-halobenzoic acids and amidines via microwave-assisted iron-catalyzed cyclization with or without ligand in water (methods A and B) or DMF (methods C and D). With these methods, moderate to high yields of the desired products can be obtained from even inactive substrates, such as guanidines. To the best of our knowledge, this is the first report on the synthesis of N-heterocyclic compounds by iron-catalyzed C-N coupling in aqueous media. The Royal Society of Chemistry 2009.
- Zhang, Xiaodong,Ye, Deju,Sun, Haifeng,Guo, Diliang,Wang, Jiang,Huang, He,Zhang, Xu,Jiang, Hualiang,Liu, Hong
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experimental part
p. 1881 - 1888
(2011/02/27)
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- Synthesis of substituted benzylamino- and heterocyclylmethylamino carbodithioate derivatives of 4-(3H)-quinazolinone and their cytotoxic activity
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A new series of substituted benzylamino- and heterocyclylmethylamino carbodithioate derivatives of 4-(3H)-quinazolinone were synthesized via four steps starting from 2-amino-5-methyl-benzoic acid and initially screened against A-549 (human non-small cell
- Cao, Sheng-Li,Feng, Yu-Ping,Zheng, Xiao-Lin,Jiang, Yu-Yang,Zhang, Mei,Wang, Yue,Xu, Meng
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p. 250 - 254
(2007/10/03)
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- Synthesis and in vitro antitumor activity of 4(3H)-quinazolinone derivatives with dithiocarbamate side chains
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A series of 4(3H)-quinazolinone derivatives with dithiocarbamate side chains were synthesized and tested for their in vitro antitumor activity against human myelogenous leukemia K562 cells. Among them, (3,4-dihydro-2-methyl-4- oxoquinazolin-6-yl)methyl 4-(4-fluorophenyl)piperazine-1-carbodithioate 8q exhibited significant inhibitory activity against K562 cells with IC 50 value of 0.5 μM.
- Cao, Sheng-Li,Feng, Yu-Ping,Jiang, Yu-Yang,Liu, Shi-Ying,Ding, Guo-Yu,Li, Run-Tao
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p. 1915 - 1917
(2007/10/03)
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- Folate analogues. 32. Synthesis and biological evaluation of 2-desamino-2-methyl-N10-propargyl-5,8-dideazafolic acid and related compounds
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The chemical synthesis of three close analogues (2-4) of N10-propargyl-5,8-dideazafolate (PDDF) is described. The quinazoline ring of 2 and 4 was constructed from the pivotal intermediate 9 in a novel and unambiguous manner during the final ste
- Patil,Jones,Nair,Galivan,Maley,Kisliuk,Gaumont,Duch,Ferone
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p. 1284 - 1289
(2007/10/02)
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