Synthesis of novel (E)-2-(4-(1H-1,2,4-triazol-1-yl)styryl)-4- (alkyl/arylmethyleneoxy)quinazoline derivatives as antimicrobial agents

Yang, Lan; Ge, Shijia; Huang, Jian; Bao, Xiaoping

doi:10.1007/s11030-017-9792-1

Cited by 29 publications

(12 citation statements)

References 43 publications

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“…The structure activity relationship of compound (carboxamidotriazolylbenzoic acid) substitution at position C-6 of coumarin core displayed promising activity towards A. viscosus as compared with compound 3b . The compound 3b with triazolylbenzoic acid substitute in the C-7 position exhibited highest activity towards the bacterial strains of S. aureus “Viotko”, and compound 3c with the substitution of 3-ethynylcoumarin with methyl-anthranilate exhibited remarkable antibacterial activity against the strains of S. aureus [ 31 ]. …”

Section: Main Textmentioning

confidence: 99%

Triazole analogues as potential pharmacological agents: a brief review

2021

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Background A large number of studies have recently reported that, because of their significant biological and pharmacological properties, heterocyclic compounds and their derivatives have attracted a strong interest in medicinal chemistry. The triazole nucleus is one of the most important heterocycles which has a feature of natural products as well as medicinal agents. Heterocyclic nitrogen is abundantly present in most medicinal compounds. The derivatization of triazole ring is based on the phenomenon of bio-isosteres in which substituted the oxygen atom of oxadiazole nucleus with nitrogen triazole analogue. Main text This review focuses on recent synthetic procedure of triazole moiety, which comprises of various pharmacological activities such as antimicrobial, anticonvulsant, anti-inflammatory, analgesic, antitubercular, anthelmintic, antioxidant, antimalarial, antiviral, etc.. Conclusion This review highlights the current status of triazole compounds as different multi-target pharmacological activities. From the literature survey, triazole is the most widely used compound in different potential activities.

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Section: Main Textmentioning

confidence: 99%

Triazole analogues as potential pharmacological agents: a brief review

2021

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“…As quinazoline and triazole are well-explored as antimicrobial agents, [98][99][100][101][102][103][104][105] Yang et al designed triazolyl-linked quinazoline hybrids. 106 As many styryl quinazolines have been reported to have anti-microbial and anti-mycobacterial activities, 107,108 hence, styryl quinazolines were considered over simple ones. Also, various alkyl (aryl) methyleneoxy units were incorporated on the quinazoline backbone in order to study its effect on the anti-microbial activity.…”

Section: Anti-tubercular Hybridsmentioning

confidence: 99%

Recent advances in the pharmacological diversification of quinazoline/quinazolinone hybrids

2020

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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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Synthesis of novel (E)-2-(4-(1H-1,2,4-triazol-1-yl)styryl)-4- (alkyl/arylmethyleneoxy)quinazoline derivatives as antimicrobial agents

Cited by 29 publications

References 43 publications

Triazole analogues as potential pharmacological agents: a brief review

Triazole analogues as potential pharmacological agents: a brief review

Recent advances in the pharmacological diversification of quinazoline/quinazolinone hybrids

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

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