Synthesis, characterization, x-ray structure and antimicrobial activity of N-(4-chlorophenyl)-2-(pyridin-4- ylcarbonyl) hydrazinecarbothioamide

Bhat, Mashooq A.; Khan, Abdul Arif; Ghabbour, Hazem A.; Quah, Ching Kheng; Fun, Hoong‐Kun

doi:10.4314/tjpr.v15i8.22

Cited by 17 publications

(6 citation statements)

References 10 publications

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“…The activity of these compounds is strongly dependent on the nature of the heteroatom as well as on the forms of thiosemicarbazide and thiocarbazide moieties. 8 3.2. Spectral analysis 3.2.1.…”

Section: Inclusion Of ML Molecular Structure Determination Conformati...mentioning

confidence: 99%

“…There are several examples where TSCZ and TCHZ have been shown to possess a broad range of biological activities such as antibacterial, anticancer, antifungal, anthelmintic, antitubercular, antiparasitic, antiviral anti-HIV, insecticidal, anti-sclerotic, antioxidant and insulin mimetic properties. [3][4][5][6][7][8] The alternation in the reductive transformation of ribonucleotide to deoxyribonucleotide causing hindrance in DNA production could be attributed to the antitumor action of TSCZ and TCHZ. 9 They also play an important role in the regulation of plant growth.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Spectroscopic characterization, molecular docking and machine learning studies of sulphur containing hydrazide derivatives

Shukla,

Rawat,

Sharma

et al. 2023

Phys. Chem. Chem. Phys.

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Section: Inclusion Of ML Molecular Structure Determination Conformati...mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Spectroscopic characterization, molecular docking and machine learning studies of sulphur containing hydrazide derivatives

Shukla,

Rawat,

Sharma

et al. 2023

Phys. Chem. Chem. Phys.

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“…Chemically, thiosemicarbazides are the simplest hydrazine derivatives of thiocarbamic acid. They contain the NH 2 -NH-C(=S)NH 2 group in their structure, thus constituting them sulfur equivalents of semicarbazide functionality [ 14 ]. This structure provides thiosemicarbazide derivatives versatile applications in the synthesis of heterocyclic compounds and biological properties different from those of semicarbazide [ 15 ].…”

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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“…These compounds are synthesized not only as potential drugs, but also as precursors for the synthesis of heterocyclic compounds such as oxadiazoles, thiadiazoles and triazoles [ 22 , 23 ]. Thiosemicarbazides ( Figure 1 A) are the simplest hydrazine derivatives of thiocarbamic acid, containing NH 2 -NH-C (=S) NH 2 moiety in the structure of molecules [ 24 ]. The 1,3,4-thiadiazoles ( Figure 1 B) formed as a result of their cyclization are molecules containing in their structure a five-membered heterocyclic ring composed of two nitrogen atoms and one sulfur atom [ 25 ].…”

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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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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Synthesis, characterization, x-ray structure and antimicrobial activity of N-(4-chlorophenyl)-2-(pyridin-4- ylcarbonyl) hydrazinecarbothioamide

Cited by 17 publications

References 10 publications

Spectroscopic characterization, molecular docking and machine learning studies of sulphur containing hydrazide derivatives

Spectroscopic characterization, molecular docking and machine learning studies of sulphur containing hydrazide derivatives

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

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

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