Synthesis, Antimicrobial Evaluation, and Molecular Modeling Studies of New Thiosemicarbazide‐Triazole Hybrid Derivatives of (<i>S</i>)‐Naproxen

Han, M. İhsan; İnce, Ufuk; Gündüz, Miyase Gözde; Küçükgüzel, Ş. Güniz

doi:10.1002/cbdv.202100900

Cited by 9 publications

(10 citation statements)

References 31 publications

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“…The tests showed a moderate potential of the tested compounds against S. aureus ATCC 29213 and MRSA. The demonstrated MIC value against two strains of S. aureus was similar to that demonstrated by our compounds and was in the range of 64–256 μg/mL [ 19 ]. D. Bhakiaraj et al, in a study from 2021 also showed the potential of compounds from the group of thiosemicarbazides with tetrazole ring against strains belonging to S. aureus [ 17 ].…”

Section: Resultssupporting

confidence: 75%

“…In recent years, scientists have been interested in the use of small organic molecules, including heterocyclic compounds, as promising therapeutic substances [ 3 , 4 , 5 , 6 , 7 , 8 , 9 ]. Literature data from our review indicate that 1,3,4-thiadiazole derivatives and intermediates in their synthesis, 1,4-disubstituted thiosemicarbazides, are commonly reported as promising antimicrobial agents [ 1 , 10 , 11 , 12 , 13 , 14 , 15 , 16 , 17 , 18 , 19 ]. Compounds containing these structures often show higher activity than standard antibacterial drugs, such as penicillin [ 10 ].…”

Section: Introductionmentioning

confidence: 99%

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Design, Synthesis, Antibacterial Evaluations and In Silico Studies of Novel Thiosemicarbazides and 1,3,4-Thiadiazoles

et al. 2022

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The emergence of drug-resistant bacterial strains continues to be one of the major challenges of medicine. For this reason, the importance of searching for novel structures of antibacterial drugs chemically different from the currently known antibiotics is still of great importance. In this study, we synthesized the thiosemicarbazide and 1,3,4-thiadiazole derivatives and tested them for antibacterial activity. In in vitro tests, we examined the activity of the synthesized substances against Gram-positive and Gram-negative bacteria strains. While all 1,3,4-thiadiazoles tested lacked significant activity, the antimicrobial response of the thiosemicarbazides was moderate and it was also dependent on the type and position of the substituent on the phenyl ring. The highest activity towards all Gram-positive bacteria strains was shown by all three linear compounds containing the trifluoromethylphenyl group in the structure. The MIC (minimum inhibitory concentration) values were in the range of 3.9–250 µg/mL. Additionally, we try to explain the mechanism of the antibacterial activity of the tested compounds using the molecular docking to DNA gyrase and topoisomerase IV, following previous reports on the molecular basis of the activity of thiosemicarbazides. Docking simulations allow the purposing dual mechanism of the antibacterial activity of the synthesized compounds through inhibition of topoisomerase IV DNA gyrase with the moderate prevalence of the topoisomerase pathway.

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Section: Resultssupporting

confidence: 75%

Section: Introductionmentioning

confidence: 99%

Design, Synthesis, Antibacterial Evaluations and In Silico Studies of Novel Thiosemicarbazides and 1,3,4-Thiadiazoles

et al. 2022

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“…One group of substances among which it is justified to search for new compounds with possible uses in the treatment of infectious diseases is thiosemicarbazide derivatives. There are many research studies showing their anti-tuberculosis [ 6 ], antiviral [ 7 ], and antibacterial properties [ 8 , 9 , 10 , 11 , 12 , 13 ]. Compounds from the group of thiosemicarbazide derivatives are synthesized not only as potential bioactive molecules but also as precursors for the synthesis of heterocyclic compounds, such as thiadiazoles, oxadiazoles, and triazoles.…”

Section: Introductionmentioning

confidence: 99%

The Importance of Substituent Position for Antibacterial Activity in the Group of Thiosemicarbazide Derivatives

Janowska,

Stefańska,

Khylyuk

et al. 2024

Molecules

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The search for new antibacterial compounds is still a huge challenge for scientists. Each new chemotherapy drug is not 100% effective when introduced into treatment. Bacteria quickly become resistant to known structures. One promising group of new compounds is thiosemicarbazides. In the presented work, we looked for the relationship between structure and antibacterial activity within the group of thiosemicarbazide derivatives. This is a continuation of our previous work. Here, we decided to check to what extent the position of the 3-methoxyphenyl substituent affects potency. We obtained new structures that differ in the positions of the substituent in the thiosemicarbazide skeleton. Based on the obtained results of the biological tests, it can be concluded that the substituent in position 1 of thiosemicarbazide derivatives significantly determines their activity. Generally, among the substituents used, trifluoromethylphenyl turned out to be the most promising. The MIC values for compounds with this substituent are 64 µg/mL towards Staphylococci sp. Using molecular docking, we tried to explain the mechanism behind the antibacterial activity of the tested compounds.

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“…Hydrazine-1-carbothioamide (3-thiosemicarbazide) derivatives received considerable attention owing to their diverse chemotherapeutic activities [ 1 ]. Several mono- and di-substituted- N -hydrazine-1-carbothioamides were reported to possess marked anticancer [ 2 , 3 , 4 , 5 , 6 , 7 , 8 , 9 ], antifungal [ 10 , 11 , 12 ], antituberculous [ 13 , 14 , 15 ], antiviral [ 16 , 17 ], antibacterial [ 18 , 19 , 20 , 21 , 22 ], and antiprotozoan activities [ 23 , 24 , 25 , 26 ]. In addition, several hydrazine-1-carbothioamide derivatives were recognized as potent urease inhibitors [ 27 , 28 , 29 , 30 , 31 , 32 ].…”

Section: Introductionmentioning

confidence: 99%

X-ray Structures and Computational Studies of Two Bioactive 2-(Adamantane-1-carbonyl)-N-substituted Hydrazine-1-carbothioamides

et al. 2022

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Two biologically active adamantane-linked hydrazine-1-carbothioamide derivatives, namely 2-(adamantane-1-carbonyl)-N-(tert-butyl)hydrazine-1-carbothioamide) 1 and 2-(adamantane-1-carbonyl)-N-cyclohexylhydrazine-1-carbothioamide 2, have been synthesized. X-ray analysis was conducted to study the effect of the t-butyl and cyclohexyl moieties on the intermolecular interactions and conformation of the molecules in the solid state. X-ray analysis reveals that compound 1 exhibits folded conformation, whereas compound 2 adopts extended conformation. The Hirshfeld surface analysis indicates that the contributions of the major intercontacts involved in the stabilization of the crystal structures do not change much as a result of the t-butyl and cyclohexyl moieties. However, the presence and absence of these contacts is revealed by the 2D-fingerprint plots. The CLP–Pixel method was used to identify the energetically significant molecular dimers. These dimers are stabilized by different types of intermolecular interactions such as N–H···S, N–H···O, C–H···S, C–H···O, H–H bonding and C–H···π interactions. The strength of these interactions was quantified by using the QTAIM approach. The results suggest that N–H···O interaction is found to be stronger among other interactions. The in vitro assay suggests that both compounds 1 and 2 exhibit urease inhibition potential, and these compounds also display moderate antiproliferative activities. Molecular docking analysis shows the key interaction between urease enzyme and title compounds.

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Synthesis, Antimicrobial Evaluation, and Molecular Modeling Studies of New Thiosemicarbazide‐Triazole Hybrid Derivatives of (S)‐Naproxen

Cited by 9 publications

References 31 publications

Design, Synthesis, Antibacterial Evaluations and In Silico Studies of Novel Thiosemicarbazides and 1,3,4-Thiadiazoles

Design, Synthesis, Antibacterial Evaluations and In Silico Studies of Novel Thiosemicarbazides and 1,3,4-Thiadiazoles

The Importance of Substituent Position for Antibacterial Activity in the Group of Thiosemicarbazide Derivatives

X-ray Structures and Computational Studies of Two Bioactive 2-(Adamantane-1-carbonyl)-N-substituted Hydrazine-1-carbothioamides

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