Synthesis and antimicrobial activities of novel 1,4-benzothiazine derivatives

Dabholkar, Vijay V.; Gavande, Rahul P.

doi:10.1016/j.arabjc.2011.03.009

Cited by 23 publications

(16 citation statements)

References 6 publications

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“…The synthesized derivatives had been evaluated in vitro against Gram-positive Bacillus subtilis and Staphylococcus aureus, and Gram-negative Klebsiella pneumoniae, Escherichia coli, and Salmonella typhi. DMSO was used as a solvent and control [13][14][15][16].…”

Section: Antibacterial Screeningmentioning

confidence: 99%

Synthesis, Antimicrobial Evaluation, Density Functional Theory, and Docking Studies of Some New 2-Mercapto Pyrimidine Schiff Bases

Aljuboori

Mahmood

2019

Asian J Pharm Clin Res

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Objective: Pyrimidine derivatives are reported to possess antibacterial, antifungal, anticancer, and anticonvulsant activities. Encouraged by this remarks, we decided to synthesize novel compounds of new 2-macraptopyrimidine linked to Schiffs̕ bases. Methods: The present work involves the synthesis of new 2-mercaptopyrimidine linked to Schiffs̕ bases. The starting, 2-mercaptopyrimidine, compound (1) reacted with thiourea to afford the corresponding 1-(pyrimidin-2-yl) thiourea (2). Then compound (2) was used as the key intermediate to prepare the -1-(2-hydroxy benzylidene)-3-(pyrimidin-2-yl) thiourea (3), and (1-benzylidine)-3-(pyrimidin-2-yl) thiourea (4), through the reaction with 2-hydroxybenzaldehyde, and benzaldehyde, respectively. Results: All the synthesized compounds were characterized by Fourier-transform infrared and1H-nuclear magnetic resonance spectroscopy. The synthesized derivatives were screened for their in vitro, antibacterial activity against two Gram-positive bacteria: Bacillus subtilis and Staphylococcus aureus and four Gram-negative bacteria: Klebsiella pneumoniae, Escherichia coli, and Salmonella typhi, and the results showed that most of them have good antibacterial activity. While their antifungal activity against three fungi species (Aspergillus fumigates, Aspergillus niger, Aspergillus terrus and Rhizopus) revealed that compounds (2-4) displayed the most potent antifungal activity. Density functional theory (DFT) calculations for the synthesized 2-mercapto pyrimidine derivatives were conducted, using a molecular structure with optimized geometry. Highest occupied molecular orbital/lowest unoccupied molecular orbital energies and structures are demonstrated. Conclusion: The antimicrobial activity indicates that compounds (3) and (4) are the most active than the compounds (1) and (2). Molecular docking revealed that compounds (3) and (4), with bulky phenyl groups are essential to blocking the active centers of glucose -6-phosphate synthase in the bacteria and fungi.

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Section: Antibacterial Screeningmentioning

confidence: 99%

Synthesis, Antimicrobial Evaluation, Density Functional Theory, and Docking Studies of Some New 2-Mercapto Pyrimidine Schiff Bases

Aljuboori

Mahmood

2019

Asian J Pharm Clin Res

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“…In addition, it moderately inhibits the growth of S. mutans and P. aeruginosa (14.5 and 13.5 mm, respectively). Pyrazole compounds integrated with 1,4-benzothiazine moiety have been developed by Dabholkar and Gavande [68]. Through antimicrobial assay, compound (51) was found to be the most promising candidate in this series against some Gram-positive, Gram-negative bacteria, and fungi with zone of inhibition in the range of 10-17 mm.…”

Section: Research In 2016mentioning

confidence: 99%

A Recent Update: Antimicrobial Agents Containing Pyrazole Nucleus

Ardiansah

2018

Asian J Pharm Clin Res

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Objective: In this review, we report antimicrobial candidates containing pyrazole nucleus integrated with various functionalities.Methods: research results by numerous scientists have been summarized from international journals indexed in reputed database such as Scopus and Web of Science.Results: Pyrazole derivatives are much of interest as potent bioactive molecules. They have shown large bioactivities especially antimicrobial performance against broad spectrum of bacterial strains.Conclusion: Several designed pyrazole derivates possessed good to superior antimicrobial activities.

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“…1,4-Benzothiazine derivatives constitute an important class of natural products possessing a wide range of biological and pharmaceutical activity due to the presence of the nitrogen-sulfur axis, which is considered to be one of the structural features important for their activities (Nitin et al, 2013;Gupta & Gupta, 2011). The 1,4-benzothiazine moiety is the pharmacophore of phenothiazines, which are well established anti-psychotic drugs (Barker & Miller, 1969), and is also known as the basic unit for their utility as dyestuffs (Bhikan & Bhata, 2015), photographic developers (Dabholkar & Gavande, 2016), ultraviolet light absorbers and antioxidants (Dabholkar & Gavande, 2010).…”

Section: Structure Descriptionmentioning

confidence: 99%

Ethyl 3-methyl-1-oxo-4H-1,4-benzothiazine-2-carboxylate monohydrate

Baryala¹,

Bakri²,

Anouar

et al. 2018

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The organic molecule in the title hydrate, C12H13NO3S·H2O, is folded across the S...N vector. Chains two molecules thick extending along the a-axis direction are formed by N—H...O and O—H...O hydrogen bonds. These interactions are reinforced by C—H...S hydrogen bonds and offset π-stacking interactions between centrosymmetrically related benzene rings. The chains are associated through C—H...O hydrogen bonds.

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Synthesis and antimicrobial activities of novel 1,4-benzothiazine derivatives

Cited by 23 publications

References 6 publications

Synthesis, Antimicrobial Evaluation, Density Functional Theory, and Docking Studies of Some New 2-Mercapto Pyrimidine Schiff Bases

Synthesis, Antimicrobial Evaluation, Density Functional Theory, and Docking Studies of Some New 2-Mercapto Pyrimidine Schiff Bases

A Recent Update: Antimicrobial Agents Containing Pyrazole Nucleus

Ethyl 3-methyl-1-oxo-4H-1,4-benzothiazine-2-carboxylate monohydrate

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