New triazole and triazolothiadiazine derivatives as possible antimicrobial agents

Kaplancıklı, Zafer Asım; Turan-Zitouni, Gülhan; Özdemir, Ahmet; Revial, Gilbert

doi:10.1016/j.ejmech.2007.03.019

Cited by 148 publications

(72 citation statements)

References 20 publications

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“…Most of them have been shown to possess diverse biological activities [2][3][4][5], such as antibacterial, antifungal, antithyroid, hypoglycaemic and antidepressant Schiff bases also constitute a good type of biologically active substructure. Studies of pyrazole Schiff base-type fungicides and triazole compounds containing the hydrazonecarbonyl group have been reported [6].…”

Section: Discussionmentioning

confidence: 99%

Crystal structure of (E)-4-(benzylideneamino)-3-(2-ethoxyphenyl)1H-1,2,4-triazole-5(4H)-thione, C17H16N4OS

Ding¹,

Huangi²,

Sun³

et al. 2009

Zeitschrift Für Kristallographie - New Crystal Structures

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C17H16N4OS, monoclinic, P\2\k\ (no. 14), a = 7.9578(9) Â, b = 15.466(2) Â, c = 13.964(2) k,ß = 92.177(2)°, V= 1717.3 Â 3 , Ζ = 4, R gt (F) = 0.073, = 0.168, Γ =273 Κ. Source of materialThe title compound was prepared by the reaction of 4-amino-3-(2-ethoxyphenyl)-liM,2,4-triazole-5(4//)-thione (0.002 mol) and benzaldehyde (0.002 mol) with a little concentrated hydrochloric acid in ethanol (20 ml). The mixture was refluxed for 3 h and the solid obtained on cooling was filtered, washed with cold water, dried and recrystallized from ethanol to give the title compound. The purified product was dissolved in ethanol and single crystals were obtained after 5 days by slow evaporation of the ethanol solution at room temperature. The key intermediate triazole was prepared from 2-ethoxybenzoic acid hydrazide (prepared from 2-ethoxybenzoic acid), following the literature method of [1]. Experimental detailsThe HI atom was refined subject to the restraint d{Ν-Η) = 0.85(3) Â. The other H atoms were positioned geometrically and alio wed to ride on their parent atoms at distances of d(Csp 2 -H) = 0.93 Â with i/iso = 1.2 i/eq(parent atom), and d(Csp 3 -H) = 0.96 or 0.97 Â with i/iso =1.5 l/eq(parent atom). The huge R values may be attributed to the weak diffraction intensity of the sample crystal. DiscussionHeterocyclic compounds containing a 1,2,4-triazole group have attracted considerable attention over the past two decades. Most of them have been shown to possess diverse biological activities [2][3][4][5], such as antibacterial, antifungal, antithyroid, hypoglycaemic and antidepressant Schiff bases also constitute a good type of biologically active substructure. Studies of pyrazole Schiff base-type fungicides and triazole compounds containing the hydrazonecarbonyl group have been reported [6]. In the title crystal structure, the bond lengths and angles are usual. The five-membered triazole ring and two benzene rings are each essentially planar. The triazole and the benzene ring (C1-C6) make a dihedral angle of 57.3(1)°, and the dihedral angle between the triazole and the benzene ring (C10-C15) is 34.3 (2)°. Both the S-C and C-Ν bond lengths are in good agreement with the values observed in related compounds. The short C-Ν bond lengths of 1.294(3) A for NI-C7 and 1.251(3) Â for N4-C9 [7][8][9], respectively, suggest partially localized double bonds.

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Section: Discussionmentioning

confidence: 99%

Crystal structure of (E)-4-(benzylideneamino)-3-(2-ethoxyphenyl)1H-1,2,4-triazole-5(4H)-thione, C17H16N4OS

Ding¹,

Huangi²,

Sun³

et al. 2009

Zeitschrift Für Kristallographie - New Crystal Structures

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“…It is well known that reaction of hydrazine hydrate with 1,3,4-oxadiazolethione IV in ethanol gives 4-amino-1,2,4-triazole-thione I. [1][2][3][4][5][6][7][8][9][10][11][12][13] We wondered what would happen in its reaction with S-alkylated 1,3,4-oxadiazoles V and N-alkylated 1,3,4-oxadiazole-thiones VI. We doubted the report 19 that reaction of V with hydrazine hydrate leads to replacement of S-alkyl with a hydrazino group without breakdown of the oxadiazole moiety.…”

Section: Introductionmentioning

confidence: 99%

“…They show antimicrobial, [1][2][3][4][5][6][7] antiproliferative, 8 antituberculosis, [9][10][11] anticonvulsant, 12 analgesic, 13 anti-inflammatory, 14 antitumor 15 and antidepressant 16 activities in addition to their inhibitory activity of trans-cinnamate 4-hydroxylase 17 and urease 18 enzymes. On this basis, searching for the synthesis of new 4-amino-1,2,4-triazole-thione derivatives is justified.…”

Section: Introductionmentioning

confidence: 99%

A new direct synthetic access to 4-amino-2-N-(glycosyl/propyl)-1,2,4-triazole-3-thiones via hydrazinolysis of 3-N-((acylated glycosyl)/allyl)-1,3,4-oxadiazole-2-thiones

Boraei¹

2016

Arkivoc

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Hydrazinolysis of 3-N-alkyl-1,3,4-oxadiazole-2-thiones yielded 2-N-alkyl-4-amino-1,2,4-triazole-2-thiones in a straightforward new direct procedure. Whereas, hydrazinolysis of alkylsulfanyl-1,3,4-oxadiazole derivatives resulted in the opening of the oxadiazole ring and loss of the alkyl moiety, instead of a nucleophilic substitution at the electrophilic carbon or triazole formation. Thio-aza-Claisen rearrangement of the allyl moiety in 4-amino-1,2,4-triazole was successfully achieved by fusion at atmospheric pressure in the absence of solvents and catalysts.

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“…Despite a large number of antibiotics and chemotherapeutics available for medical use, at the same time, the emergence of old and new antibiotic resistance created revealed a substantial medical need for new classes of antimicrobial agents 3 . There is no doubt that the existing arsenal of antimicrobial agents we have in hand for the treatment of infectious diseases is insufficient to protect us over the long term [4][5][6][7] .…”

Section: Introductionmentioning

confidence: 99%

Synthesis, antimicrobial activity and cytotoxicity of some new carbazole derivatives

Kaplancıklı

Yurttaş

Turan-Zitouni

et al. 2011

Journal of Enzyme Inhibition and Medicinal Chemistry

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New triazole and triazolothiadiazine derivatives as possible antimicrobial agents

Cited by 148 publications

References 20 publications

Crystal structure of (E)-4-(benzylideneamino)-3-(2-ethoxyphenyl)1H-1,2,4-triazole-5(4H)-thione, C17H16N4OS

Crystal structure of (E)-4-(benzylideneamino)-3-(2-ethoxyphenyl)1H-1,2,4-triazole-5(4H)-thione, C17H16N4OS

A new direct synthetic access to 4-amino-2-N-(glycosyl/propyl)-1,2,4-triazole-3-thiones via hydrazinolysis of 3-N-((acylated glycosyl)/allyl)-1,3,4-oxadiazole-2-thiones

Synthesis, antimicrobial activity and cytotoxicity of some new carbazole derivatives

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