6-Phenyl-3-(4-pyridyl)-1,2,4-triazolo-[3,4-b][1,3,4]thiadiazole: Synthesis, experimental, theoretical characterization and biological activities

Cansız, Ahmet; Çetin, Ahmet; Örek, Cahit; Karatepe, Mustafa; Sarac, Kamiran; Kus, Alper; Koparır, Pelin

doi:10.1016/j.saa.2012.07.016

Cited by 16 publications

(10 citation statements)

References 57 publications

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“…The bond lengths and angles within the triazolo-thiadiazole system of the refined structure agreed well with the reference structures (Lu et al ., 2008; Khan et al ., 2009, 2014; Fan et al ., 2010; Cansız et al ., 2012; Wu, 2013; Gündoğdu et al ., 2017) and the optimized structures (Table III). The Ortep-3 (Farrugia, 2012) diagram of the compound with thermal ellipsoids at the 50% probability level is shown in Figure 4.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and structural characterization of 3-[1-[4-(2-methylpropyl)phenyl]ethyl]-6-(4-fluorophenyl)-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazole

et al. 2019

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3-[1-[4-(2-Methylpropyl)phenyl]ethyl]-6-(4-fluorophenyl)-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazole (C21H21FN4S) has been synthesized as a member of a series of triazolothiadiazoles having NSAIDs moieties with cytotoxic activity. The crystal structure of this new compound has been solved and refined using conventional laboratory X-ray powder diffraction data and optimized using density functional techniques. The final structure solution was achieved by Rietveld refinement using soft restraints on all non-H atom bond lengths and angles. This compound crystallizes in $P\bar{1}\;$ space group, with the unit cell parameters a = 5.5880(4) Å, b = 9.3074(7) Å, c = 19.497(4) Å, α = 99.311(10)°, β = 91.925(9)°, γ = 98.199(6)°, and V = 988.8(2) Å3. To complement and verify the structure solution of the compound, the density functional theory (DFT) calculations were performed by using the local density approximation and the generalized gradient approximation for exchange-correlation energy. In order to see the effect of the van der Waals interactions on the electronic structure, the relevant structure was also optimized with B3LYP-D2, PBE-D2, and optB88-vdW functionals. The refined crystal structure was confirmed by the DFT calculations. The best agreement with the experimental structure was achieved by optB88-vdW functional.

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Section: Resultsmentioning

confidence: 99%

Synthesis and structural characterization of 3-[1-[4-(2-methylpropyl)phenyl]ethyl]-6-(4-fluorophenyl)-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazole

et al. 2019

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“…In 13 C NMR spectra signals appeared at δ 151.00 and 165.56 indicates 3 rd and 5 th Carbon of triazole moiety respectively, other signals were appeared at the presupposed chemical shifts. As per the general methods reported, compound ( 5 ) was reacted with substituted benzoic/pyridinyl acids in phosphorous oxychloride at reflux temperature for 8–10 h to gives 6‐substituted‐3‐[5‐(3‐fluoro‐4‐methoxy‐phenyl)‐1 H ‐pyrazol‐3‐yl]‐[1, 2,4]triazolo[3, 4‐b][1, 3,4]thiadiazole derivatives ( 6 a‐l ). IR spectra with absence of NH 2 and SH stretching vibrations and absence of NH 2 and SH protons in NMR suggesting formation of 6‐substituted‐3‐[5‐(3‐fluoro‐4‐methoxy‐phenyl)‐1 H ‐pyrazol‐3‐yl]‐[1, 2,4]triazolo[3, 4‐b][1, 3,4]thiadiazole derivatives ( 6 a‐l ).…”

Section: Resultsmentioning

confidence: 99%

Synthesis, Antimicrobial Evaluation and Docking Study of Some Pyrazole Bearing [1, 2,4]Triazolo[3, 4‐b][1, 3,4]thiadiazole Derivatives

Shingare¹,

Patil²,

Sangshetti³

et al. 2018

ChemistrySelect

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A novel series of pyrazole bearing [1,2,4]triazolo [3, 4-b] [1,3,4] thiadiazole derivatives (6 a-l) such as 3-(5-(3-fluoro-4-methoxyphenyl)-1H-pyrazol-3-yl)-6-(2-methoxyphenyl)- [1,2,4]triazolo [3, 4-b] [1,3,4]thiadiazole were synthesized by cyclo-condensation of 4-amino-5-[5-(3-fluoro-4-methoxy-phenyl)-1H-pyrazol-3yl]-4H-[1, 2,4]triazole-3-thiol (5) with substituted benzoic/pyridinyl acids in phosphorus oxychloride giving good yields and purity. IR, 1 H NMR, 13 C NMR and LCMS/MS spectroscopy were used to characterise all the synthesized compounds. All the new derivatives were appraised for their antimicrobial activity, antifungal assay against C. Albicans, A. Niger and A. Clavatus along with Nystatin and Griseofulvin as standard drug and antibacterial assay against E. Coli, P. Aeruginosa, S. Aureus, S. Pyogenus along with Ampicillin as standard drug. Compounds (6 b) and (6 j) displayed excellent antifungal activity whereas compound (6 d) and (6 e) displayed excellent antibacterial activity. Molecular modelling and adsorption, distribution, metabolism and excretion-toxicity (ADMET) prediction data clearly shows that 1,2,4-triazolo[3, 4-b][1, 3,4] thiadiazole derivatives (6 a-l) have potential to explore in the drug discovery pipeline as antifungal agents.

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“…Activity of S-substituted derivatives of bistriazolethione 13 depends on the nature of the substituent. The free radical scavenging activity of compounds containing alkyl groups (15)(16)(17)(18)(19)(20) was approx. 50 %, whereas that of 22 containing benzyl group was only 3.61 %.…”

Section: Evaluation Of Antioxidative Propertiesmentioning

confidence: 99%

“…1,3,4-Thiadiazoles are another important class of heterocyclic compounds due to their numerous biological activities [3] including anticancer [11][12][13], antimicrobial and antifungal [14,15], and antioxidative [16] ones.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and biological activity of 1,3,4-oxa(thia)diazole, 1,2,4-triazole-5-(thio)one and S-substituted derivatives of 3-((2-carboxyethyl)phenylamino)propanoic acid

et al. 2015

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A series of novel derivatives of 3-((2-carboxyethyl)phenylamino)propanoic acid bearing two identical substituted 1,3,4-oxadiazole, 1,3,4-thiadiazole, or 1,2,4-triazole moieties were synthesized and their molecular structures were confirmed by IR, 1 H, 13 C NMR spectroscopy, and elemental analysis data. The synthesized compounds were screened for their reducing power, free radical scavenging, plant growth regulating, and antimicrobial properties. 5,5 0 -((Phenylazanediyl)bis(ethane-2,1-diyl))bis(4-phenyl-2,4-dihydro-3H-1,2,4-triazole-3-thione) showed excellent antioxidant activity, three times higher than that of the antibiotic control (cefazolin). 2,2 0 -((((Phenylazanediyl)bis(ethane-2,1-diyl))bis(4-phenyl-4H-1,2,4-triazole-5,3-diyl))bis(sulfanediyl))diacetate exhibited notable bactericidal activity against Pseudomonas aeruginosa with MBC and MIC values 7.3 lg/ml, whereas 12 compounds displayed significant fungicidal activity against Candida albicans with MIC value 3.9 lg/ml. Graphical Abstract Synthesis of compounds 2-27. R: 2,5,7,10,13,[15][16][17][18][19][20][21][22][23][24][25][26][27]3,8,4,9,12

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6-Phenyl-3-(4-pyridyl)-1,2,4-triazolo-[3,4-b][1,3,4]thiadiazole: Synthesis, experimental, theoretical characterization and biological activities

Cited by 16 publications

References 57 publications

Synthesis and structural characterization of 3-[1-[4-(2-methylpropyl)phenyl]ethyl]-6-(4-fluorophenyl)-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazole

Synthesis and structural characterization of 3-[1-[4-(2-methylpropyl)phenyl]ethyl]-6-(4-fluorophenyl)-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazole

Synthesis, Antimicrobial Evaluation and Docking Study of Some Pyrazole Bearing [1, 2,4]Triazolo[3, 4‐b][1, 3,4]thiadiazole Derivatives

Synthesis and biological activity of 1,3,4-oxa(thia)diazole, 1,2,4-triazole-5-(thio)one and S-substituted derivatives of 3-((2-carboxyethyl)phenylamino)propanoic acid

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