Antimicrobial and Cytotoxicity Activities of 2-(aryl)-3-(benzo[d][1,3] dioxol-5-yl)thiazolidin-4-ones

Souza, Samilly Evangelista; Masteloto, Hellen G.; Silva, Daniel Santos da; Azambuja, Juliana H.; Braganhol, Elizandra; Ribeiro, Juliana Silva; Lund, Rafael Guerra; Cúnico, Wilson

doi:10.2174/1570180814666170106143418

Cited by 2 publications

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“…The N-acylhydrazone functional group, -C(O)-NH-N CH-, is found in many compounds having important and diverse biological activities (Fraga & Barreiro, 2006;Singh et al, 2016), including their use in the fight against tuberculosis, especially the drug-resistant forms (Cardoso et al, 2011;Souza et al, 2017). Specifically, N-acylhydrazonyl-containing 2Hchromene derivatives have been found to possess significant anti-mycobacterial activities (Angelova et al, 2017;Cardoso et al, 2011).…”

Section: Chemical Contextmentioning

confidence: 99%

Crystal structures and Hirshfeld surface analyses of (E)-N′-benzylidene-2-oxo-2H-chromene-3-carbohydrazide and the disordered hemi-DMSO solvate of (E)-2-oxo-N′-(3,4,5-trimethoxybenzylidene)-2H-chromene-3-carbohydrazide: lattice energy and intermolecular interaction energy calculations for the former

Gomes¹,

Low²,

Wardell³

et al. 2019

Acta Cryst E

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The crystal structures of the disordered hemi-DMSO solvate of (E)-2-oxo-N′-(3,4,5-trimethoxybenzylidene)-2H-chromene-3-carbohydrazide, C20H18N2O6·0.5C2H6OS, and (E)-N′-benzylidene-2-oxo-2H-chromene-3-carbohydrazide, C17H12N2O3 (4: R = C6H5), are discussed. The non-hydrogen atoms in compound [4: R = (3,4,5-MeO)3C6H2)] exhibit a distinct curvature, while those in compound, (4: R = C6H5), are essential coplanar. In (4: R = C6H5), C—H...O and π–π intramolecular interactions combine to form a three-dimensional array. A three-dimensional array is also found for the hemi-DMSO solvate of [4: R = (3,4,5-MeO)3C6H2], in which the molecules of coumarin are linked by C—H...O and C—H...π interactions, and form tubes into which the DMSO molecules are cocooned. Hirshfeld surface analyses of both compounds are reported, as are the lattice energy and intermolecular interaction energy calculations of compound (4: R = C6H5).

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Section: Chemical Contextmentioning

confidence: 99%

Crystal structures and Hirshfeld surface analyses of (E)-N′-benzylidene-2-oxo-2H-chromene-3-carbohydrazide and the disordered hemi-DMSO solvate of (E)-2-oxo-N′-(3,4,5-trimethoxybenzylidene)-2H-chromene-3-carbohydrazide: lattice energy and intermolecular interaction energy calculations for the former

Gomes¹,

Low²,

Wardell³

et al. 2019

Acta Cryst E

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Synthesis and Antimicrobial Activity of Thiohydantoins Obtained from L-Amino Acids

Camargo

Jhonatan

Renata

et al. 2019

LDDD

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Background: Thiohydantoins are an important class of heterocyclic compounds in drug discovery since they are related to a wide range of biological properties including antimicrobial activity. Objective: The objective of this study was to synthesize a series of thiohydantoins derived from Laminoacids and to evaluated their inhibitory effect on the growth of Gram-negative and Grampositive bacteria. Methods: All title compounds were synthetized by reaction of L-amino acids with thiourea or ammonium thiocyanate. Their antimicrobial activities were evaluated against bacterial strains by broth microdilution assays. The time-kill kinetics, the antibiofilm activity and the cytotoxicity to mammalian cells were determined for the compound that exhibited the best antimicrobial profile (1b). Results: Eleven thiohydantoins were readily obtained in good yields (52-95%). In general, thiohydantoins were more effective against Gram-positive bacteria. Compound 1b (derived from Lalanine) showed the best antibacterial activity against Staphylococcus epidermis ATCC 12228 and S. aureus BEC 9393 with MIC values of 940 and 1921 µM, respectively. The time-kill kinetics demonstrated time-dependent bactericidal effect in both strains for this derivative. Besides, 1b also exhibited antibacterial activity against biofilms of S. epidermidis ATCC 12228, leading to a 40% reduction in their metabolic activity compared to the untreated control. No cytotoxicity of 1b to mammalian cells was observed at MIC values. Conclusion: The data reported herein indicate relevant antimicrobial activity of thiohydantoins derived from L-aminoacid, mainly 1b, as potential pharmacophore to guide further chemical modification aiming at the search for new and improved antimicrobial agents.

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Antimicrobial and Cytotoxicity Activities of 2-(aryl)-3-(benzo[d][1,3] dioxol-5-yl)thiazolidin-4-ones

Cited by 2 publications

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Synthesis and Antimicrobial Activity of Thiohydantoins Obtained from L-Amino Acids

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