Synthesis and Antibacterial Activity of 2‐substitued‐(3‐pyridyl)‐quinazolinone Derivatives

Zhang, Li; Chen, Qin; Li, Xiaoqin; Wu, Shou‐Qun; Wan, Jin‐Lin; Ouyang, Gangfeng

doi:10.1002/jhet.3099

Cited by 15 publications

(4 citation statements)

References 31 publications

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“…[1][2][3][4][5][6][7] Among heterocyclic compounds quinazolines are well-recognized for their pharmacological properties, such as anticonvulsant [8], antihypertensive [9] and vasodilator [10]. The interest in the quinazolinic structure, due to its wide range of biological activities, [11][12][13][14][15][16][17][18][19] led to a many number of different synthetic pathways to access this quinazolines nucleus. Quinazolinone are divided into subcategories like 2-quinazolinone (a) and 4-quinazolinone (b) based on the substitution on quinazolinones shown in Figure 1.…”

Section: Introductionmentioning

confidence: 99%

Novel oxo-5-(trifluoromethyl)quinazolinyl amide derivatives and their anticancer activity

Pandiri,

Konda,

Chennuri

et al. 2023

Preprint

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A series of novel oxo-5-(trifluoromethyl)quinazolinyl amide derivatives were prepared starting from 2-aminobenzoic acid 1, reacted with 4-Chlorobenzoyl chloride and obtained 2-(4-Chlorophenyl)-5-(trifluoromethyl)-4H-benzo[d][1, 3]oxazin-4-one 2, compound 2 on reaction with hydroxyl amine and obtained 2-(4-Chlorophenyl)-3-(4-hydroxyphenyl)-5-(trifluoromethyl)quinazolin-4(3H)-one 3, compound 3 on further react with bromoethyl acetate to get ethyl 2-(4-(2-(4-chlorophenyl)-4-oxo-5-(trifluoromethyl)quinazolin-3(4H)-yl) phenoxy) acetate 4, compound 4 on reaction with aliphatic and aryl amine to obtain amide functionalized quinazolinyl derivatives 5. All the final compounds evaluated for anti cancer activity against four human cancer cell lines such as ‘HeLa - Cervical cancer (CCL-2); COLO 205- Colon cancer (CCL-222); HepG2- Liver cancer (HB-8065); MCF7 - Breast cancer (HTB-22)’ and promising compounds 5l and 5m have been identified.

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Section: Introductionmentioning

confidence: 99%

Novel oxo-5-(trifluoromethyl)quinazolinyl amide derivatives and their anticancer activity

Pandiri,

Konda,

Chennuri

et al. 2023

Preprint

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“…Quinazolines have a broad range of pharmacological applications, in addition to their low toxicity profiles [ 3 ]. Quinazoline frameworks have great pharmacological activities as antioxidant [ 7 , 8 , 9 ], antidiabetic [ 10 , 11 , 12 ], antibacterial [ 13 , 14 , 15 ], antiviral [ 16 , 17 , 18 ], antimicrobial [ 19 , 20 , 21 ], anticancer [ 22 , 23 ], antihistaminic [ 24 , 25 , 26 ], antidiuretic [ 27 , 28 ], antitubercular [ 29 , 30 , 31 ], and anti-inflammatory [ 32 , 33 , 34 ] agents. Quinazolinones are a type of quinazoline derivative that are biologically active in the same way as quinazoline [ 35 ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, X-ray Structure, Hirshfeld, DFT and Biological Studies on a Quinazolinone-Nitrate Complex

et al. 2022

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The reaction of 4-hydroxyquinazoline (4HQZ) with aqueous solution of nitric acid afforded the corresponding quinazolinone-nitrate (4HQZN) complex in very good yield. The crystal structure of 4HQZN was determined and its structural and supramolecular structural aspects were analyzed. 4HQZN crystallized in the space group P21/c and monoclinic crystal system with one [4HQZ-H]+[NO3]− formula and Z = 4. Its supramolecular structure could be described as a 2D infinite layers in which the 4HQZN molecules are connected via N-H…O and C-H…O hydrogen bridges. Using DFT calculations, the relative stability of five suggested isomers of 4HQZN were predicted. It was found that the medium effects have strong impact not only on the isomers’ stability but also on the structure of the 4HQZN. It was found that the structure of 4HQZN in DMSO and methanol matched well with the reported X-ray structure which shed the light on the importance of the intermolecular interactions on the isomers’ stability. The structure of 4HQZN could be described as a proton transfer complex in which the nitrate anion acting as an e-donor whiles the protonated 4HQZ is an e-acceptor. In contrast, the structure of the isolated 4HQZN in gas phase and in cyclohexane could be described as a 4HQZ…HNO3 hydrogen bonded complex. Biological screening of the antioxidant, anticancer and antimicrobial activities of 4HQZ and 4HQZN was presented and compared. It was found that, 4HQZN has higher antioxidant activity (IC50 = 36.59 ± 1.23 µg/mL) than 4HQZ. Both of 4HQZ and 4HQZN showed cell growth inhibition against breast (MCF-7) and lung (A-549) carcinoma cell lines with different extents. The 4HQZ has better activity with IC50 of 178.08 ± 6.24 µg/mL and 119.84 ± 4.98 µg/mL, respectively. The corresponding values for 4HQZN are 249.87 ± 9.71 µg/mL and 237.02 ± 8.64 µg/mL, respectively. Also, the antibacterial and antifungal activities of 4HQZN are higher than 4HQZ against all studied microbes. The most promising result is for 4HQZN against A. fumigatus (MIC = 312.5 mg/mL).

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“…In recent years, quinazolinones have gradually attracted the attention of scholars in the creation of new pesticides. The existing research results showed that quinazolinone derivatives have antiviral, , antibacterial, antifungal, and other activities in the prevention and treatment of plant diseases. As an important pharmacophore of the antibacterial agents, such as fluquinconazole and proquinazid (Figure ), quinazolinone has received high attention due to its simple and variable structure …”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis, Antibacterial Activity, Antiviral Activity, and Mechanism of Myricetin Derivatives Containing a Quinazolinone Moiety

et al. 2021

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Plant bacteria such as Xanthomonas axonopodis pv. citri (Xac), Pseudomonas syringae pv. actinidiae (Psa), Xanthomonas oryzae pv. oryzae (Xoo), and tobacco mosaic virus (TMV) have created huge obstacles to the global trade of food and economic crops. However, traditional chemical agents used to control these plant diseases have gradually become disadvantageous due to long-term irregular use. Therefore, finding new and efficient antibacterial and antiviral agents is becoming imperative. In this study, a series of myricetin derivatives containing a quinazolinone moiety were designed and synthesized, and the antibacterial and antiviral activities of these compounds were evaluated. The bioassay results showed that some target compounds exhibited good antibacterial activities in vitro and antiviral activities in vivo. Among them, the median effective concentration (EC50) value of compound L18 against Xac was 16.9 μg/mL, which was better than those of the control drugs bismerthiazol (BT) (62.2 μg/mL) and thiodiazole copper (TC) (97.5 μg/mL). Scanning electron microscopy (SEM) results confirmed that compound L18 inhibited the growth of Xac by affecting the morphology of cells. Microscale thermophoresis (MST) test results indicated that the dissociation constant (K d) value of compound L11 against TMV-CP was 0.012 μM, which was better than that of the control agent ningnanmycin (2.726 μM). This study reveals that myricetin derivatives containing a quinazolinone moiety are potential antibacterial and antiviral agents.

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Synthesis and Antibacterial Activity of 2‐substitued‐(3‐pyridyl)‐quinazolinone Derivatives

Cited by 15 publications

References 31 publications

Novel oxo-5-(trifluoromethyl)quinazolinyl amide derivatives and their anticancer activity

Novel oxo-5-(trifluoromethyl)quinazolinyl amide derivatives and their anticancer activity

Synthesis, X-ray Structure, Hirshfeld, DFT and Biological Studies on a Quinazolinone-Nitrate Complex

Design, Synthesis, Antibacterial Activity, Antiviral Activity, and Mechanism of Myricetin Derivatives Containing a Quinazolinone Moiety

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