Synthesis and molecular docking study of pyrazole clubbed oxazole as antibacterial agents

Desai, N. C.; Vaja, Darshita V.; Joshi, Surbhi B.; Khedkar, Vijay M.

doi:10.1007/s11164-020-04286-6

Cited by 16 publications

(4 citation statements)

References 18 publications

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“…A first possibility is to add various substituents on the diphenyl sulfone fragment, like nitro or fluoro, e.g., by using other aromatic compounds in the Friedel–Crafts sulfonylation. Desai et al showed that the nitro group leads to a better efficacy against S. pyogenes , whereas the presence of the fluorine atom could increase the affinity for the active site of DNA gyrase [ 55 ]. The predictive studies indicated a high degree of similarity of 4a and 2 with CHEMBL4520114 and CHEMBL4544788, respectively outlining a potential future synthesis approach.…”

Section: Discussionmentioning

confidence: 99%

Synthesis and Biological Evaluation of New N-Acyl-α-amino Ketones and 1,3-Oxazoles Derivatives

et al. 2021

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In order to develop novel bioactive substances with potent activities, some new valine-derived compounds incorporating a 4-(phenylsulfonyl)phenyl fragment, namely, acyclic precursors from N-acyl-α-amino acids and N-acyl-α-amino ketones classes, and heterocycles from the large family of 1,3-oxazole-based compounds, were synthesized. The structures of the new compounds were established using elemental analysis and spectral (UV-Vis, FT-IR, MS, NMR) data, and their purity was checked by reversed-phase HPLC. The newly synthesized compounds were evaluated for their antimicrobial and antibiofilm activities, for toxicity on D. magna, and by in silico studies regarding their potential mechanism of action and toxicity. The 2-aza-3-isopropyl-1-[4-(phenylsulfonyl)phenyl]-1,4-butanedione 4b bearing a p-tolyl group in 4-position exhibited the best antibacterial activity against the planktonic growth of both Gram-positive and Gram-negative strains, while the N-acyl-α-amino acid 2 and 1,3-oxazol-5(4H)-one 3 inhibited the Enterococcus faecium biofilms. Despite not all newly synthesized compounds showing significant biological activity, the general scaffold allows several future optimizations for obtaining better novel antimicrobial agents by the introduction of various substituents on the phenyl moiety at position 5 of the 1,3-oxazole nucleus.

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Section: Discussionmentioning

confidence: 99%

Synthesis and Biological Evaluation of New N-Acyl-α-amino Ketones and 1,3-Oxazoles Derivatives

et al. 2021

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“…A first choice for the future improvement of these derivatives is to replace the chlorine atom from the arylsulfonylphenyl moiety with various substituents, e.g., an iodine atom, trifluoromethyl, or nitro groups. It was observed that the introduction of an electron-withdrawing group (such as NO 2 ) on aromatic rings increased the antibacterial potency of the compounds [ 78 ]. Furthermore, it was demonstrated that the iodine atom is more active than the other halogens, multiple-halogen-substituted derivatives displayed best antibacterial activity than their respective mono-halogen-substituted derivatives, hydrophobic groups (e.g., tert -butyl, benzyloxy) linked to the aryl moiety deliver prominent antibacterial activity [ 77 ].…”

Section: Discussionmentioning

confidence: 99%

Synthesis, In Silico and In Vitro Evaluation of Antimicrobial and Toxicity Features of New 4-[(4-Chlorophenyl)sulfonyl]benzoic Acid Derivatives

et al. 2021

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The multi-step synthesis, physico-chemical characterization, and biological activity of novel valine-derived compounds, i.e., N-acyl-α-amino acids, 1,3-oxazol-5(4H)-ones, N-acyl-α-amino ketones, and 1,3-oxazoles derivatives, bearing a 4-[(4-chlorophenyl)sulfonyl]phenyl moiety are reported here. The structures of the newly synthesized compounds were confirmed by spectral (UV-Vis, FT-IR, MS, 1H- and 13C-NMR) data and elemental analysis results, and their purity was determined by RP-HPLC. The new compounds were assessed for their antimicrobial activity and toxicity to aquatic crustacean Daphnia magna. Also, in silico studies regarding their potential mechanism of action and toxicity were performed. The antimicrobial evaluation revealed that the 2-{4-[(4-chlorophenyl)sulfonyl]benzamido}-3-methylbutanoic acid and the corresponding 1,3-oxazol-5(4H)-one exhibited antimicrobial activity against Gram-positive bacterial strains and the new 1,3-oxazole containing a phenyl group at 5-position against the C. albicans strain.

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Section: Introductionmentioning

confidence: 99%

“…Additionally, our research group has reported the synthesis, antimicrobial activity, and molecular docking of compounds like pyrimidine clubbed pyrazoles, [33] quinazoline clubbed thiazoles, 1,3,4-oxadiazoles, [8] 2-azetidinone, quinolines, [34] and pyrazole clubbed oxazoles. [35] On the basis of the above-mentioned facts and to achieve new potent antimicrobial agents, we describe the synthesis, structure elucidation, and structure-activity relationship (SAR) of a series of were treated with acetic anhydride to produce the targeted compounds 4a-l. The structures of the synthesized compounds 4a-l were interpreted by spectroscopic techniques like IR, 1 H nuclear magnetic resonance (NMR), 13 C NMR, and mass spectroscopy.…”

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confidence: 99%

In silico molecular docking studies of oxadiazole and pyrimidine bearing heterocyclic compounds as potential antimicrobial agents

Desai

Vaghani

Jethawa

et al. 2021

Archiv der Pharmazie

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Microbial resistance is a major problem faced by the scientific community. It has created an urgent need to develop antimicrobial agents with novel structures and mechanisms of action. With this aim, a series of novel 1,3,4‐oxadiazoles bearing 3,4‐dihydropyrimidine heterocyclic motifs 4a–l were designed and synthesized. One‐pot Biginelli synthesis is pivotal due to the use of readily available chemicals, shorter reaction time, and ecofriendly synthesis with a good yield. The structures of the synthesized molecules were characterized and confirmed by infrared, 1H nuclear magnetic resonance (NMR), 13C NMR, and mass spectroscopic techniques. The title compounds were screened against Gram‐positive and ‐negative strains of bacteria and fungi using the Mueller–Hinton broth method. Compound 4d was found to be the most promising against Escherichia coli (12.5 µg/ml), whereas the same compound showed good activity against Staphylococcus aureus at a concentration of 50 µg/ml. Other compounds of the same series, 4c and 4h, displayed moderate activity against Streptococcus pyogenes at a concentration of 50 µg/ml. Furthermore, results of the antifungal activity tests revealed that compound 4i showed promising activity against all the strains of fungi, Candida albicans, Aspergillus niger, and Aspergillus clavatus, at concentrations of 100, 50, and 100 µg/ml, respectively. Molecular docking also showed that these compounds had a significant binding affinity (Glide docking score: −7.74 to −6.531) for DNA gyrase, engaging in a series of bonded and nonbonded interactions with residues lining the active site. The results of molecular docking study validated the experimental findings, thereby providing an initiation mark to optimize this motif using a structure‐based drug design approach.

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Synthesis and molecular docking study of pyrazole clubbed oxazole as antibacterial agents

Cited by 16 publications

References 18 publications

Synthesis and Biological Evaluation of New N-Acyl-α-amino Ketones and 1,3-Oxazoles Derivatives

Synthesis and Biological Evaluation of New N-Acyl-α-amino Ketones and 1,3-Oxazoles Derivatives

Synthesis, In Silico and In Vitro Evaluation of Antimicrobial and Toxicity Features of New 4-[(4-Chlorophenyl)sulfonyl]benzoic Acid Derivatives

In silico molecular docking studies of oxadiazole and pyrimidine bearing heterocyclic compounds as potential antimicrobial agents

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