Synthesis, structure, and antifungal evaluation of some novel 1,2,4-triazolylmercaptoacetylthiosemicarbazide and 1,2,4-triazolylmercaptomethyl-1,3,4-thiadiazole analogs

Klip, Nalan Terzioğlu; Çapan, Gültaze; Gürsoy, Aysel; Uzun, Meltem; Şatana, Dilek

doi:10.3109/14756360903040439

Cited by 15 publications

(6 citation statements)

References 16 publications

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“…The analytical and spectral data belonging compound 4 were described in the literature as following: [ 53–55 ]…”

Section: Methodsmentioning

confidence: 99%

“…The starting compounds 1-4 were prepared as described in the literature. [50][51] 2-((4-(4-Bromophenyl)-5-(furan-2-yl)-4H-1,2,4triazol-3-yl)thio)acetohydrazide 4The analytical and spectral data belonging compound 4 were described in the literature as following: [53][54][55] M.p. 171-172 C. IR υ max (KBr, cm The analytical and spectral data belonging compound 5b were reported in the literature.…”

Section: General Procedures For the Synthesis Of Compounds 1-4mentioning

confidence: 99%

“…171-172 C. IR υ max (KBr, cm The analytical and spectral data belonging compound 5b were reported in the literature. [55] 2- ( The analytical and spectral data belonging compound 5d were reported in the literature. [55] 2-(2-((4-(4-Bromophenyl)-5-(furan-2-yl)-4H-1,2,4triazol-3-yl)thio)acetyl)-N-phenylhydrazinecar bothioamide (5e)…”

Section: General Procedures For the Synthesis Of Compounds 1-4mentioning

confidence: 99%

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

Dincel

Ulusoy‐Güzeldemirci

Şatana

et al. 2020

Journal of Heterocyclic Chem

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A series of novel hydrazinecarbothioamide (5a,c,f), 4‐thiazolidinone (6a‐e), and 1,2,4‐triazole‐3‐thione (7a‐d) were designed and synthesized. The structural elucidations of the novel compounds were performed by IR, 1H‐NMR, 13C‐NMR, mass and elemental analysis. All novel derivatives were evaluated for their antibacterial and antifungal activities against nine diverse microorganisms. According to the biological activity studies of the compounds, 6d, 7c and 7d displayed hope promising antibacterial activity. Furthermore, 6d displayed potent antifungal activity. Consequently, the obtained results revealed that 6d, 7c and 7d present a leading structure for future drug development due to its straightforward synthesis and relevant bioactivity.

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“…The analytical and spectral data belonging compound 4 were described in the literature as following: [ 53–55 ]…”

Section: Methodsmentioning

confidence: 99%

Section: General Procedures For the Synthesis Of Compounds 1-4mentioning

confidence: 99%

Section: General Procedures For the Synthesis Of Compounds 1-4mentioning

confidence: 99%

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

Dincel

Ulusoy‐Güzeldemirci

Şatana

et al. 2020

Journal of Heterocyclic Chem

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“…Both types of compounds bearing aliphatic and aromatic substituents inhibited the growth of fungal strains at concentrations ranging between 4 and 8 μg/mL, the most susceptible microorganism being T. mentagrophytes (MIC value of 4 μg/mL). 90 …”

Section: Antibacterial and Antifungal Activitiesmentioning

confidence: 99%

2-Amino-1,3,4-thiadiazole as a potential scaffold for promising antimicrobial agents

Şerban¹,

Stănăşel²,

Șerban³

et al. 2018

DDDT

130

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Pathogenic microorganisms are causative agents for different types of serious and even lethal infectious diseases. Despite advancements in medication, bacterial and fungal infections continue to be a growing problem in health care. As more and more bacteria become resistant to antibiotics used in therapy and an increasing number of invasive fungal species become resistant to current antifungal medications, there is considerable interest in the development of new compounds with antimicrobial activity. The compounds containing a heterocyclic ring play an important role among organic compounds with biological activity used as drugs in human and veterinary medicine or as insecticides and pesticides in agriculture. Thiadiazoles belong to the classes of nitrogen–sulfur heterocycles with extensive application as structural units of biologically active molecules and as useful intermediates in medicinal chemistry. The potency of the thiadiazole nucleus is demonstrated by the drugs currently used. 1,3,4-Thiadiazoles and some of their derivatives are extensively studied because of their broad spectrum of pharmacological activities. The aim of this review was to highlight the main antimicrobial properties exhibited by derivatives possessing 2-amino-1,3,4-thiadiazole moiety. Many of the reported 2-amino-1,3,4-thiadiazole derivatives can be considered as lead compounds for drug synthesis, and several of them have demonstrated higher antimicrobial activity in comparison to standard drugs. Furthermore, taking into account the reactivity of the amine group in the derivatization process, 2-amino-1,3,4-thiadiazole moiety may be a good scaffold for future pharmacologically active 1,3,4-thiadiazole derivatives.

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“…Due to the bioisosterism between oxygen and sulphur atoms, 1,3,4-thiadiazoles possess similar physical and chemical properties to 1,3,4-oxadiazoles. The extensive literature survey revealed that 1,3,4-thiadiazole derivatives exhibit antifungal activity [ 12 , 13 , 14 , 15 , 16 ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Oxadiazole-Thiadiazole Hybrids and Their Anticandidal Activity

et al. 2017

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In the field of infection management, it is a major challenge to discover a potent and safe antifungal agent due to the emergence of resistant strains. Hence, the goal of this paper is to design and synthesize novel oxadiazole-thiadiazole hybrid compounds (6a–6s) and evaluate their antifungal activity. The structures of synthesized compounds were elucidated by various methods including FT-IR, 1H-NMR, 13C-NMR and HR-MS spectral data. Compounds were tested against four Candida species by broth microdilution assay. Compounds 6e, 6k and 6r, bearing a nitro group, showed significant antifungal activity against all fungi with minimum inhibitory concentration (MIC) in the range of 0.78–3.12 µg/mL. These compounds were also screened for their in vitro cytotoxic effects by MTT assay and detected as nontoxic at their active concentrations against Candida strains. To examine the effects of these compounds on ergosterol biosynthesis, the LC-MS-MS method, which is based on quantification of ergosterol level in C. krusei, was carried out. Finally, the most active molecule (6e) was docked in the active site of the lanosterol 14α-demethylase enzyme, and it was determined that there is a strong interaction between the compound and enzyme.

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Synthesis, structure, and antifungal evaluation of some novel 1,2,4-triazolylmercaptoacetylthiosemicarbazide and 1,2,4-triazolylmercaptomethyl-1,3,4-thiadiazole analogs

Cited by 15 publications

References 16 publications

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

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

2-Amino-1,3,4-thiadiazole as a potential scaffold for promising antimicrobial agents

Synthesis of Oxadiazole-Thiadiazole Hybrids and Their Anticandidal Activity

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