Synthesis, antimicrobial and anti-inflammatory activities of some 1,2,4-triazolo[3,4-b][1,3,4]thiadiazoles and 1,2,4-triazolo[3,4-b][1,3,4]thiadiazines bearing trichlorophenyl moiety

Karegoudar, Prakash; Prasad, Davinder; Ashok, Mithun; Mahalinga, Manjathuru; Poojary, Boja; Holla, B. Shivarama

doi:10.1016/j.ejmech.2007.06.026

Cited by 130 publications

(60 citation statements)

References 13 publications

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“…The antibacterial results showed no obvious activities for monotriazolium compounds 5a, 5f, and 5g with short C 2 -C 4 alkyl chain against S. aureus ATCC 29213, E. coli ATCC 25922, B. subtilis, and B. proteus. But good activities were observed for compounds 5b, 5c, 5d, and 5e containing long alkyl chains with lengths in the range of C 8 -C 16 . Among the tested alkyl mono-triazolium compounds, dodecyl triazolium derivatives 5c and 5e showed the most potent antibacterial activity with low MIC values between 1.05 and 8.38 lM against all tested strains.…”

Section: Antibacterial Activitymentioning

confidence: 92%

“…2) exhibited significant antifungal activities [15]. In addition, many investigations could show that the introduction of variable aromatic and aliphatic substituents could markedly affect the biological activities of triazole derivatives, especially some halogen-substituted aromatic compounds such as 2,4-dichlorobenzyl, 2,4-difluorobenzyl ones, were found to be biologically important and could improve the antimicrobial activities [16,17].…”

Section: Introductionmentioning

confidence: 99%

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Synthesis, Antibacterial and Antifungal Activities of Novel 1,2,4‐Triazolium Derivatives

Luo

Gan

et al. 2009

Archiv der Pharmazie

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A series of novel 1,2,4-triazolium derivatives was synthesized starting from commercially available 1H-1,2,4-triazole, 2,4-dichlorobenzyl chloride, or 2,4-difluorobenzyl bromide. Their antibacterial and antifungal activities were evaluated against Staphylococcus aureus ATCC 29213, Escherichia coli ATCC 25922, Bacillus proteus, Bacillus subtilis, Pseudomonas aeruginosa, Candida albicans ATCC 76615, and Aspergillus fumigatus. All structures of the new compounds were confirmed by NMR, IR, and MS spectra, and elemental analyses. The antimicrobial tests showed that most of synthesized triazolium derivatives exhibit significant antibacterial and antifungal activities in vitro. 1-(2,4-Difluorobenzyl)-4-dodecyl-1H-1,2,4-triazol-4-ium bromide and 1-(2,4-Dichlorobenzyl)-4-dodecyl-1H-1,2,4- triazol-4-ium bromide were the most potent compounds against all tested strains with the MIC values ranging from 1.05 to 8.38 microM. They exhibited much stronger activities than the standard drugs chloramphenicol and fluconazole which are in clinical use. The results also showed that the antimicrobial activities of triazolium derivatives depend upon the type of substituent, the length of the alkyl chain, and the number of triazolium rings.

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Section: Antibacterial Activitymentioning

confidence: 92%

Section: Introductionmentioning

confidence: 99%

Synthesis, Antibacterial and Antifungal Activities of Novel 1,2,4‐Triazolium Derivatives

Luo

Gan

et al. 2009

Archiv der Pharmazie

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“…In the first step, aminomercaptotriazoles required as starting material was prepared by heating 3-(4-methoxyphenyl)/ (3,4,5-trimethoxyphenyl)propionic acids with thiocarbohydrazide at the melting temperature (160-170°C) [8,9]. Aminomercaptotriazoles were converted into 6-phenyl-7H-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazines in one step by reacting them with phenacyl bromide in anhydrous ethanol under reflux [9][10][11] (Scheme 1). The structures of the compounds are characterized by elementary analysis, IR, 1 H-NMR, and mass spectra.…”

Section: Synthesismentioning

confidence: 99%

A joint theoretical and experimental structural study of two novel 1,2,4-triazolo[3,4-b]-1,3,4-thiadiazine derivatives

2010

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In this study, two novel 1,2,4-triazolo[3,4-b]-1,3,4-thiadiazine derivatives, 3-[2-(4-methoxyphenyl)ethyl] -6-phenyl-7H-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazine (compound 1) and 3-[2-(3,4,5-trimethoxyphenyl)ethyl]-6-phenyl-7H-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazine (compound 2), having analgesic-anti-inflammatory activity were synthesized and characterized by IR, 1 H-NMR, and mass spectroscopic techniques besides elementary analysis. Additionally, the structures and molecular packings of the mentioned compounds have been investigated by X-ray single crystal diffraction. The six-membered thiadiazine ring adopts the screw boat conformation in both the compounds. In the crystal packings of the compounds 1 and 2, C-HÁÁÁN and C-HÁÁÁO interactions link the molecules into a twodimensional network and generate infinite chains. Furthermore, C-HÁÁÁp intermolecular interactions provide further stability to the molecular packing in both the molecules. The conformers have been predicted by the potential energy surface scan employing the AM1 method. Geometry optimizations and electrostatic properties have been obtained using AM1 and ab initio quantum methods.

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“…Also, [1,2,4]triazolo [5,1-b] [1,3,5]thiadiazines were prepared by di-Mannich reaction. Encouraged by the above observations and in connection with our previous review articles about biologically active heterocyclic systems, [10][11][12][13][14] we decided to carry out a detailed literature survey of different triazolothiadiazines during the period from 1990 till now.…”

Section: Introductionmentioning

confidence: 99%

Recent Progress in the Synthetic Routes to Triazolothiadiazines

Abdel‐Wahab

Althagafi

2014

Phosphorus, Sulfur, and Silicon and the Related Elements

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Synthesis, antimicrobial and anti-inflammatory activities of some 1,2,4-triazolo[3,4-b][1,3,4]thiadiazoles and 1,2,4-triazolo[3,4-b][1,3,4]thiadiazines bearing trichlorophenyl moiety

Cited by 130 publications

References 13 publications

Synthesis, Antibacterial and Antifungal Activities of Novel 1,2,4‐Triazolium Derivatives

Synthesis, Antibacterial and Antifungal Activities of Novel 1,2,4‐Triazolium Derivatives

A joint theoretical and experimental structural study of two novel 1,2,4-triazolo[3,4-b]-1,3,4-thiadiazine derivatives

Recent Progress in the Synthetic Routes to Triazolothiadiazines

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