Antimicrobial activities of some synthesized 1-(3-(2-methylphenyl)-4-Oxo-3H-quinazolin-2-yl-4-(substituted)thiosemicarbazide derivatives

Alagarsamy, V.; Anjana, G. V.; Sulthana, M. T.; Parthiban, P.; Solomon, V. Raja

doi:10.1134/s106816201603002x

Cited by 6 publications

(3 citation statements)

References 17 publications

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“…Quinazolin‐4(3 H )‐ones and 4 H ‐benzo[ d ][1,3]thiazin‐4‐ones are important heterocyclic frameworks with various biological and pharmaceutical activities (Scheme ). Quinazolin‐4(3 H )‐ones exhibit an extensive range of promising activities, including antimalarial, antibacterial, antiviral, antidepressant, anti ‐inflammatory and anticancer activities . In particular, 2‐thioxo‐2,3‐dihydroquinazolin‐4(1 H )‐ones are versatile building blocks with a cyclic thiourea moiety used commonly as intermediates toward various quinazolinone‐containing molecules, including fluquinconazole .…”

Section: Methodsmentioning

confidence: 99%

Temperature‐Controlled Base‐Promoted Cyclization for the Synthesis of 2‐Amino‐4H‐benzo[d][1,3]thiazin‐4‐ones and 2‐Thioxo‐4(3H)‐quinazolinones

Zhou

Jia

et al. 2017

Asian J Org Chem

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Section: Methodsmentioning

confidence: 99%

Temperature‐Controlled Base‐Promoted Cyclization for the Synthesis of 2‐Amino‐4H‐benzo[d][1,3]thiazin‐4‐ones and 2‐Thioxo‐4(3H)‐quinazolinones

Zhou

Jia

et al. 2017

Asian J Org Chem

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“…Isoniazid activated by mycobacterial tuberculosis, KatG forms isonicotinic acyl‐NADH complex, this complex binds tightly to the InhA, which was most important step for an inhibition of mycobacterial. The antituberculosis activity of quinoline , pyrrole , imidazole , and thiosemicarbazide derivatives have been reported. Several studies gave promising results and the economic advantage of synthesized molecules and their biological activity.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Docking, ADME‐Tox Study of 2‐(2‐(2‐Chlorophenyl)quinoline‐4‐carbonyl)‐N‐substituted hydrazinecarbothioamide Derivatives and Their Biological Evaluation

Patel

Vekariya

Patel

et al. 2018

Journal of Heterocyclic Chem

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A series of 2‐(2‐(2‐chlorophenyl)quinoline‐4‐carbonyl)‐N‐substituted hydrazinecarbothioamide derivatives were synthesized by facile and efficient conventional method. The structures of the compounds were elucidated with the aid of an elemental analysis, IR, ESI‐MS, 1H‐NMR, and 13C‐NMR spectral data. The synthesized compounds were evaluated for their in vitro antibacterial, antifungal, antimalarial, and antituberculosis activity against standard drugs. The bacterial studies were determined against gram‐positive and negative bacteria. These compounds were found to a broad spectrum of activity against the screened bacteria, but poor activity was observed against Pseudomonas aeruginosa and Escherichia coli. Compounds 8d, 8f, 8i, 8l, and 8n showed the potent activity against Staphylococcus aureus. Compounds 8d, 8g, 8k, 8l, and 8q show the potent activity against antimalarial as compared with the standard drugs Chloroquine, Quinine and compounds 8h, 8n, and 8o shows mild activity against H37Rv strain. Molecular docking revealed that synthesized derivatives and target proteins were actively involved in a binding pattern and had a significant corelation with biological activity. We have also performed a molecular dynamics and ADME‐Tox parameters for the synthesized compounds.

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“…2-Aminoquinazolin-4(3 H )-ones are derived from the quinazolinone class of compounds, which have been extensively explored in a wide range of therapeutic areas, whereas literature references on 2-aminoquinazolinones are relatively scarce. Secondary and tertiary 2-amino analogues have been found to have pharmacological relevance, with examples of antifungal, anti-inflammatory, anticancer, , antibacterial, , antihypertensive, antidepressant, and antimycobacterial activity. , On the other hand, primary 2-aminoquinazolinone derivatives have not yet been commercially developed but have shown a variety of biological activities as antimalarial, antiviral, , and anticancer agents. Although there is no known antimycobacterial activity, they appear as a valuable novel scaffold to explore as a potential anti-TB chemotype.…”

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confidence: 99%

Synthesis, Structure–Activity Relationship, and Mechanistic Studies of Aminoquinazolinones Displaying Antimycobacterial Activity

et al. 2020

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Phenotypic whole-cell screening against Mycobacterium tuberculosis ( Mtb ) in glycerol–alanine–salts supplemented with Tween 80 and iron (GASTE-Fe) media led to the identification of a 2-aminoquinazolinone hit compound, sulfone 1 which was optimized for solubility by replacing the sulfone moiety with a sulfoxide 2 . The synthesis and structure–activity relationship (SAR) studies identified several compounds with potent antimycobacterial activity, which were metabolically stable and noncytotoxic. Compound 2 displayed favorable in vitro properties and was therefore selected for in vivo pharmacokinetic (PK) studies where it was found to be extensively metabolized to the sulfone 1 . Both derivatives exhibited promising PK parameters; however, when 2 was evaluated for in vivo efficacy in an acute TB infection mouse model, it was found to be inactive. In order to understand the in vitro and in vivo discrepancy, compound 2 was subsequently retested in vitro using different Mtb strains cultured in different media. This revealed that activity was only observed in media containing glycerol and led to the hypothesis that glycerol was not used as a primary carbon source by Mtb in the mouse lungs, as has previously been observed. Support for this hypothesis was provided by spontaneous-resistant mutant generation and whole genome sequencing studies, which revealed mutations mapping to glycerol metabolizing genes indicating that the 2-aminoquinazolinones kill Mtb in vitro via a glycerol-dependent mechanism of action.

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Antimicrobial activities of some synthesized 1-(3-(2-methylphenyl)-4-Oxo-3H-quinazolin-2-yl-4-(substituted)thiosemicarbazide derivatives

Cited by 6 publications

References 17 publications

Temperature‐Controlled Base‐Promoted Cyclization for the Synthesis of 2‐Amino‐4H‐benzo[d][1,3]thiazin‐4‐ones and 2‐Thioxo‐4(3H)‐quinazolinones

Temperature‐Controlled Base‐Promoted Cyclization for the Synthesis of 2‐Amino‐4H‐benzo[d][1,3]thiazin‐4‐ones and 2‐Thioxo‐4(3H)‐quinazolinones

Synthesis, Docking, ADME‐Tox Study of 2‐(2‐(2‐Chlorophenyl)quinoline‐4‐carbonyl)‐N‐substituted hydrazinecarbothioamide Derivatives and Their Biological Evaluation

Synthesis, Structure–Activity Relationship, and Mechanistic Studies of Aminoquinazolinones Displaying Antimycobacterial Activity

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