Synthesis, Characterization, Antimycobacterial and Anticancer Evaluation of New 1,2,4-Triazole Derivatives

Cihan-Üstündağ, Gökçe; Simsek, B.; Ilhan, E.; Çapan, Gültaze

doi:10.2174/157018081131000074

Cited by 7 publications

(4 citation statements)

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“…The chemical synthesis of 3a-o and 4a-k compounds is outlined in Scheme 1 . The synthesis of several intermediate thiosemicarbazide derivatives except 2g and 2h were previously reported elsewhere 32 , 39 . 4-Thiazolidinones were prepared starting from 2-hydroxy-2-phenylacetohydrazide ( 1 ) which afforded intermediate thiosemicarbazides ( 2 ) on reaction with aryl isothiocyanates.…”

Section: Resultsmentioning

confidence: 99%

Novel thiazolidinone-containing compounds, without the well-known sulphonamide zinc-binding group acting as human carbonic anhydrase IX inhibitors

Güzel-Akdemir

Angeli

Demir

et al. 2018

Journal of Enzyme Inhibition and Medicinal Chemistry

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A small collection of 26 structurally novel thiazolidinone-containing compounds, without the well-known sulphonamide zinc-binding group, were synthesised and tested in enzyme inhibition assays against the tumour-associated hCA IX enzyme. Inhibition constants in the lower micromolar region (KI < 25 μM) have been measured for 17 of the 26 compounds. Even though the KI values are relatively weak, the fact that they do not contain a sulphonamide moiety suggests that these compounds do not interact with the active site zinc ion. Therefore, docking studies and molecular dynamics simulations have been performed to suggest binding poses for these structurally novel inhibitors.

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Section: Resultsmentioning

confidence: 99%

Novel thiazolidinone-containing compounds, without the well-known sulphonamide zinc-binding group acting as human carbonic anhydrase IX inhibitors

Güzel-Akdemir

Angeli

Demir

et al. 2018

Journal of Enzyme Inhibition and Medicinal Chemistry

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“…A large number of thiazole-containing derivatives have been reported to have a wide variety of biological activities, such as antibacterial, antifungal, antitubercular, anti-mycobacterial, anticancer and antiviral. [1][2][3][4][5][6] 2-Amino-thiazol acetate esters are present in most organic compounds of interest in biology, pharmacology, and material sciences. 7 Similarly, 1,3,4-oxadiazoles have had appealing attention for the last two decades due to their extensive range of biological activities, such as anti-inflammatory, antifungal, antiparasitic and antimicrobial effects.…”

Section: Introductionmentioning

confidence: 99%

Structure-activity relationship and in silico study of unique bi-heterocycles: 5-[(2-amino-1,3-thiazol-4-yl)methyl]-1,3,4-oxadiazole-2-thiol derivatives

Abbasi

Rehman

Siddiqui

et al. 2019

JSCS

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This paper presents the synthesis of some unique bi-heterocyclic hybrid molecules with a thiazole and an oxadiazole ring. The synthesis was initiated by the conversion of ethyl 2-(2-amino-1,3-thiazol-4-yl)acetate (1) to the corresponding 2-(2-amino-1,3-thiazol-4-yl)acetohydrazide (2) by the reaction with hydrazine hydrate in methanol. The treatment of the acid hydrazide, 2, with carbon disulfide gave the bi-heterocyclic nucleophile, 5-[(2-amino-1,3-thiazol-4-yl)methyl]-1,3,4-oxadiazole-2-thiol (3). Finally, the target compounds, 5a-o, were synthesized by stirring the nucleophile 3 with different electrophiles, 4a-o, in DMF using LiH as a base and an activator. The structures of the newly synthesized molecules were confirmed through spectroscopic techniques, such as IR, EI-MS, 1 H-NMR and 13 C-NMR. The structure-activity relationship of all these bi-heterocycles was established by evaluating them against four enzymes, namely, acetylcholinesterase, butyrylcholinesterase, urease and α-glucosidase, followed by their in silico study. Moreover, their cytotoxicity was also profiled by killing data of brine shrimps at various concentrations.

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“…Nowadays, the synthesis of nitrogen containing heterocycles is an important direction in the fields of pesticidal chemistry [ 1 – 3 ], medicinal chemistry [ 4 ], polymer chemistry [ 5 ], coordination chemistry [ 6 ] and industrial chemistry [ 7 ]. 1,2,4-Triazole derivatives and pyridine derivatives often display broad and diverse biological activities [ 8 – 10 ].…”

Section: Introductionmentioning

confidence: 99%

Microwave assisted synthesis, antifungal activity, DFT and SAR study of 1,2,4-triazolo[4,3-a]pyridine derivatives containing hydrazone moieties

Shi

et al. 2016

Chemistry Central Journal

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BackgroundThe increasing prevalence of multi-drug resistant fungal infections has encouraged the search for new antifungal agents. Hydrazone derivatives always exhibited diversity activities, including antifungal, anti-inflammatory, anti-oxidation, anti-cancer activity. Regarding the heterocyclic moiety, 1,2,4-triazolo[4,3-a]pyridine derivatives also display broad activities, such as antifungal activity, anticonvulsant activity, herbicidal activity, antimicrobial activity and anticancer activity.ResultsA series of novel 1,2,4-triazolo[4,3-a]pyridine derivatives containing hydrazone moiety were designed and synthesized from 2,3-dichloropyridine, hydrazine hydrate by multi-step reactions under microwave irradiation condition, and their structures were characterized by FT IR, 1H NMR, 13C NMR, 19F NMR, MS and elemental analysis. The antifungal activities of title compounds were determined. The results indicated that some of the title compounds exhibited good antifungal activity. Furthermore, DFT calculation was carried out for studying the structure–activity relationship (SAR).ConclusionA practical synthetic route to obtain 1,2,4-triazolo[4,3-a]pyridine derivatives is presented. This study suggests that the 1,2,4-triazolo[4,3-a]pyridine derivatives exhibited good antifungal activity.

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Synthesis, Characterization, Antimycobacterial and Anticancer Evaluation of New 1,2,4-Triazole Derivatives

Cited by 7 publications

References 0 publications

Novel thiazolidinone-containing compounds, without the well-known sulphonamide zinc-binding group acting as human carbonic anhydrase IX inhibitors

Novel thiazolidinone-containing compounds, without the well-known sulphonamide zinc-binding group acting as human carbonic anhydrase IX inhibitors

Structure-activity relationship and in silico study of unique bi-heterocycles: 5-[(2-amino-1,3-thiazol-4-yl)methyl]-1,3,4-oxadiazole-2-thiol derivatives

Microwave assisted synthesis, antifungal activity, DFT and SAR study of 1,2,4-triazolo[4,3-a]pyridine derivatives containing hydrazone moieties

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