Synthesis of some new 2, 3-diaryl-1, 3-thiazolidin-4-ones as antibacterial agents

Sayyed, Mudassar A.; Mokle, Shyam S.; Bokhare, Munjaji; Mankar, Amol; Surwase, Santhosh; Bhusare, Sudhakar R.; Vibhute, Yeshwant B.

doi:10.3998/ark.5550190.0007.221

Cited by 41 publications

(8 citation statements)

References 2 publications

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“…The introduction of a sulfenimine fragment in the structure of cephalosporin sulfoxides enhanced their inhibitory activity against cephalosporinase C. The activity was significantly affected by substituents in the sulfenimine moiety [ 24 ]. Substituted salicylic and nitrobenzylidene imines have been shown to be subjected as new chemotypes of antimicrobial drug candidates [ 25 , 26 , 27 , 28 , 29 ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Antimicrobial Activity of Sulfenimines Based on Pinane Hydroxythiols

et al. 2022

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The widespread presence of multidrug-resistant pathogenic microorganisms challenges the development of novel chemotype antimicrobials, insensitive to microbial tools of resistance. To date, various monoterpenoids have been shown as potential antimicrobials. Among many classes of molecules with antimicrobial activity, terpenes and terpenoids are an attractive basis for the design of antimicrobials because of their low toxicity and availability for various modifications. In this work, we report on the synthesis of sulfenimines from chiral trifluoromethylated and non-fluorinated pinane-type thiols. Final compounds were obtained with yields of up to 81%. Among the 13 sulfenimines obtained, 3 compounds were able to repress the growth of both bacteria (S. aureus, both MSSA and MRSA; P. aeruginosa) and fungi (C. albicans) with an MIC of 8–32 µg/mL. Although compounds exhibited relatively high cytotoxicity (the therapeutic index of 3), their chemotype can be used as a starter point for the development of disinfectants and antiseptics for targeting multidrug-resistant pathogens.

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Section: Introductionmentioning

confidence: 99%

Synthesis and Antimicrobial Activity of Sulfenimines Based on Pinane Hydroxythiols

et al. 2022

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“…[14,15] Modern fluorine-organic chemistry has dramatically widened the synthetic repertoire for the specific introduction of fluorine into organic molecules. [16][17][18][19] Numerous drugs containing fluorine include antipsychotics such as fluphenazine, HIV protease inhibitors such as fipranavir, antibiotics such as oflaxacin and trovafloxacin and anaesthetics such as halothane. [20] Fluoroquinolines are commonly used family of broad spectrum antibiotics.…”

Section: Introductionmentioning

confidence: 99%

Biological evaluation, molecular docking, DNA interaction and thermal studies of new bioactive metal complexes of 2‐hydroxybenzaldehyde and fluorobenzamine Schiff base ligand

Bengi

Maddikayala

Reddy

2020

Applied Organom Chemis

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Funding information DST-FIST Program of India Schiff base ligand named 2-((E)-(2-fluorophenylimino)methyl)phenol (HL) was prepared by the condensation of 2-hydroxybenzaldehyde and 2-fluorobenzamine in 1:1 molar ratio. The coordination behaviour of a series of transition metal ions with the synthesized HL ligand, [Cr(HL) 2 ] (1), [Fe (HL) 2 ] (2), [Co(HL) 2 ] (3) and [Cu(HL) 2 ] (4) is reported. The structure and bonding of the metal complexes have been deduced by analytical and spectral studies. Based on the above studies, the metal centres were found to be octahedral for all the complexes. The activation thermodynamic properties were calculated using the Coats-Redfern method. Thermal decomposition processes of complexes 1, 2, 3 and 4 are non-spontaneous; that is, the complexes are thermally stable. The positive value of Gibbs free energy of decomposition (ΔG*) for all the complexes is non-spontaneous processes. DNA binding properties of these metal complexes, investigated using UV-visible absorption, fluorescence and viscosity measurement studies, imply that the complexes bind to DNA by intercalation. The intrinsic binding constant K b from the electronic absorption studies are 3.12 × 10 4 M −1 , 1.86 × 10 4 M −1 , 3.96 × 10 4 M −1 and 5.89 × 10 4 M −1 , and the Stern-Volmer quenching constant K sv values from fluorescence studies are 2.29 × 10 4 M −1 , 1.92 × 10 4 M −1 , 5.62 × 10 4 M −1 and 8.91 × 10 4 M −1 , for the complexes 1, 2, 3 and 4, respectively. DNA photo cleavage activities of these complexes were studied with supercoiled pUC19 DNA, in the presence of H 2 O 2. GOLD 3.1 program was used to evaluate binding affinities of complexes with human DNA topoisomerase I protein. in vitro cytotoxic and antimicrobial studies revealed higher activity of metal complexes, compared with the ligand.

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“…Schiff bases, derived from aromatic amines and aromatic aldehydes are reported to be involved in the study of asymmetric catalysis [5] ,magnetic properties [6], photochromism [7], binding with DNA [8], construction of supra molecular structures [9], the study of activity against Ehrlichascites carcinoma (EAC) [10], the field of dyes and pigments [11], the development of corrosion inhibitors [12], anti-HIV [13] and in the evaluation of physical properties in the crystalline state [14]. Optically active imine derivatives possess multipronged biological activities such as antimicrobial [15], anticancer [16,17], antiplasmodic-antihypoxic [18], antitubularcular [19,20], nematicidal-insecticidal [21], anti-inflammatory, and lipoxygenase [22]. The imine moieties are important intermediates and versatile starting materials for the synthesis of chiral amines [23,24], pyrimidine derivatives [25], phenylhydrazones [26,27], Mannich bases [28], indoles [29], quinoxalines [30], imidazoles [31], amino triphenylmethanes [32], Michael adducts [33], allyl products [34], optically active α-alkyl aldehydes [35,36] by hydrogenation [37], nucleophilic addition with organometallics [38] and cycloaddition reaction [39].…”

Section: Introductionmentioning

confidence: 99%

Solvent-Free Synthesis and Spectral Linearity of Some (E)-2-(substituted benzylideneamino)-N-(3-chloro-4-fluorophenyl)-hexahydro-2<i>H</i>-cyclopenta[b]thiophene-3-carboxamides

Thirunarayanan

Sekar²

2013

ILCPA

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Some (E)-2-(substituted benzylideneamino)-N-(3-chloro-4-fluorophenyl)-hexahydro-2H-cyclopenta[b]thiophene-3-carboxamide derivatives have been synthesized by SiO2:H3PO4 catalyzed solvent-free condensation of 2-amino-N-(3-chloro-4-fluorophenyl)-hexahydro-2H-cyclopenta [b]thiophene-3-carboxamide and various substituted benzaldehydes in microwave irradiation. The yield of the imine-carboximido derivatives has been found to be more than 85 %. The purity of all imine-carboximido derivatives has been checked using their physical constants and spectral data. The spectral data of the imine-carboximido derivatives such as infrared ν (cm-1) of CO, NH, C-N, C-Cl, C-F, C=N, and the NMR chemical shifts (δ, ppm) of NH, CH, CO and C=N have been correlated with Hammett substituent constants, F and R parameters. From the results of statistical analysis, the effects of substituent on the above spectral group absorptions have been discussed.

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Synthesis of some new 2, 3-diaryl-1, 3-thiazolidin-4-ones as antibacterial agents

Cited by 41 publications

References 2 publications

Synthesis and Antimicrobial Activity of Sulfenimines Based on Pinane Hydroxythiols

Synthesis and Antimicrobial Activity of Sulfenimines Based on Pinane Hydroxythiols

Biological evaluation, molecular docking, DNA interaction and thermal studies of new bioactive metal complexes of 2‐hydroxybenzaldehyde and fluorobenzamine Schiff base ligand

Solvent-Free Synthesis and Spectral Linearity of Some (E)-2-(substituted benzylideneamino)-N-(3-chloro-4-fluorophenyl)-hexahydro-2<i>H</i>-cyclopenta[b]thiophene-3-carboxamides

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