Design, synthesis, characterization and antimicrobial evaluation of some novel hydrazinecarbothioamide, 4‐thiazolidinone and 1,2,4‐triazole‐3‐thione derivatives

Dincel, Efe Doğukan; Ulusoy‐Güzeldemirci, Nuray; Şatana, Dilek; Küçükbasmacı, Ömer

doi:10.1002/jhet.4159

Cited by 27 publications

(17 citation statements)

References 57 publications

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“…On the other hand, the thiazolidinone core has attracted the interest of researchers due to its various degrees of pharmacological and medicinal activities, such as antimicrobial [ 33 , 34 , 35 ], anti-inflammatory [ 36 , 37 ], anticancer [ 38 , 39 ], antiviral [ 40 , 41 ], antitubercular [ 38 , 42 ], antidiabetic [ 43 ], antioxidant [ 44 , 45 ], anticonvulsant [ 46 , 47 ], antimalarial [ 48 ], and carbonic anhydrize inhibitors [ 49 , 50 ]. Furthermore, the thiazolidinone moiety is present in the structure of many approved drugs.…”

Section: Introductionmentioning

confidence: 99%

Thiazolidin-4-Ones as Potential Antimicrobial Agents: Experimental and In Silico Evaluation

et al. 2022

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Herein, we report computational and experimental evaluations of the antimicrobial activity of twenty one 2,3-diaryl-thiazolidin-4-ones. All synthesized compounds exhibited an antibacterial activity against six Gram-positive and Gram-negative bacteria to different extents. Thus, the MIC was in the range of 0.008–0.24 mg/mL, while the MBC was 0.0016–0.48 mg/mL. The most sensitive bacterium was S. Typhimurium, whereas S. aureus was the most resistant. The best antibacterial activity was observed for compound 5 (MIC at 0.008–0.06 mg/mL). The three most active compounds 5, 8, and 15, as well as compound 6, which were evaluated against three resistant strains, MRSA, P. aeruginosa, and E. coli, were more potent against all bacterial strains used than ampicillin. The antifungal activity of some compounds exceeded or were equipotent with those of the reference antifungal agents bifonazole and ketoconazole. The best activity was expressed by compound 5. All compounds exhibited moderate to good drug-likeness scores ranging from −0.39 to 0.39. The docking studies indicated a probable involvement of E.coli Mur B inhibition in the antibacterial action, while CYP51 inhibition is likely responsible for the antifungal activity of the tested compounds. Finally, the assessment of cellular cytotoxicity of the compounds in normal human MRC-5 cells revealed that the compounds were not toxic.

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Section: Introductionmentioning

confidence: 99%

Thiazolidin-4-Ones as Potential Antimicrobial Agents: Experimental and In Silico Evaluation

et al. 2022

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“…Continuing our ongoing research in the field of antimicrobial agents [45][46][47] and based on results of our previous paper [47] we designed new series of compounds modi- On the other hand, the thiazolidinone core attracted the interest of researchers owing to its various degrees of pharmacological and medicinal activities [18,[40][41][42][43][44][45][46][47]. Herein, we explore the antimicrobial effects of benzothiazolylthiazolidin-4-one and their in silico mechanistic investigation.…”

Section: Resultsmentioning

confidence: 99%

“…On the other hand, the thiazolidinone core attracted the interest of researchers owing to its various degrees of pharmacological and medicinal activities [ 18 , 40 , 41 , 42 , 43 , 44 , 45 , 46 , 47 ]. Herein, we explore the antimicrobial effects of benzothiazolylthiazolidin-4-one and their in silico mechanistic investigation.…”

Section: Introductionmentioning

confidence: 99%

Exploration of the Antimicrobial Effects of Benzothiazolylthiazolidin-4-One and In Silico Mechanistic Investigation

et al. 2021

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Background: Infectious diseases still affect large populations causing significant morbidity and mortality. Bacterial and fungal infections for centuries were the main factors of death and disability of millions of humans. Despite the progress in the control of infectious diseases, the appearance of resistance of microbes to existing drugs creates the need for the development of new effective antimicrobial agents. In an attempt to improve the antibacterial activity of previously synthesized compounds modifications to their structures were performed. Methods: Nineteen thiazolidinone derivatives with 6-Cl, 4-OMe, 6-CN, 6-adamantan, 4-Me, 6-adamantan substituents at benzothiazole ring were synthesized and evaluated against panel of four bacterial strains S. aureus, L. monocytogenes, E. coli and S. typhimirium and three resistant strains MRSA, E. coli and P. aeruginosa in order to improve activity of previously evaluated 6-OCF3-benzothiazole-based thiazolidinones. The evaluation of minimum inhibitory and minimum bactericidal concentration was determined by microdilution method. As reference compounds ampicillin and streptomycin were used. Results: All compounds showed antibacterial activity with MIC in range of 0.12–0.75 mg/mL and MBC at 0.25–>1.00 mg/mL The most active compound among all tested appeared to be compound 18, with MIC at 0.10 mg/mL and MBC at 0.12 mg/mL against P. aeruginosa. as well as against resistant strain P. aeruginosa with MIC at 0.06 mg/mL and MBC at 0.12 mg/mL almost equipotent with streptomycin and better than ampicillin. Docking studies predicted that the inhibition of LD-carboxypeptidase is probably the possible mechanism of antibacterial activity of tested compounds. Conclusion: The best improvement of antibacterial activity after modifications was achieved by replacement of 6-OCF3 substituent in benzothiazole moiety by 6-Cl against S. aureus, MRSA and resistant strain of E. coli by 2.5 folds, while against L. monocytogenes and S. typhimirium from 4 to 5 folds.

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“…Additionally, Derivatives 143 and 144 were active against C. albicans (inhibition at 51.8 and 66.7%) and A. flavus (inhibition at 76 and 84%) [145]. Compounds 133a-133e demonstrated moderate to weak antibacterial activity against E. coli, S. aureus and P. aeruginosa at concentration of 32->64 µg/mL [137].…”

Section: Antimicrobial Activitymentioning

confidence: 98%

The Bioactivity of Thiazolidin-4-Ones: A Short Review of the Most Recent Studies

Mech

Kurowska

Trotsko

2021

IJMS

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Thiazolidin-4-ones is an important heterocyclic ring system of a pharmacophore and a privileged scaffold in medicinal chemistry. This review is focused on the latest scientific reports regarding biological activities of thiazolidin-4-ones published in 2020 and 2021. The review covers recent information about antioxidant, anticancer, anti-inflammatory, analgesic, anticonvulsant, antidiabetic, antiparasitic, antimicrobial, antitubercular and antiviral properties of thiazolidin-4-ones. Additionally, the influence of different substituents in molecules on their biological activity was discussed in this paper. Thus, this study may help to optimize the structure of thiazolidin-4-one derivatives as more efficient drug agents. Presented information may be used as a practical hint for rational design of new small molecules with biological activity, especially among thiazolidin-4-ones.

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Design, synthesis, characterization and antimicrobial evaluation of some novel hydrazinecarbothioamide, 4‐thiazolidinone and 1,2,4‐triazole‐3‐thione derivatives

Cited by 27 publications

References 57 publications

Thiazolidin-4-Ones as Potential Antimicrobial Agents: Experimental and In Silico Evaluation

Thiazolidin-4-Ones as Potential Antimicrobial Agents: Experimental and In Silico Evaluation

Exploration of the Antimicrobial Effects of Benzothiazolylthiazolidin-4-One and In Silico Mechanistic Investigation

The Bioactivity of Thiazolidin-4-Ones: A Short Review of the Most Recent Studies

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