Antituberculosis agents. Part II. α-[5-(2-Furyl)-1,3,4-oxadiazol-2-yl-thio]acetohydrazide and related compounds

Mir, Irshad Ahmad; Siddiqui, M. Tariq; Comrie, A. M.

doi:10.1039/j39710002798

Cited by 5 publications

(3 citation statements)

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“…Several 1,3,4-oxadiazole derivatives exhibit analgesic [1], antiproteolytic, anticonvulsive, anti-inflammatory [2,3], or fungicidal [4] properties. It was reported that 5-phenyl-1,3,4-oxadiazole-2-thiol is antitubercular, and 5-(3-pyridyl)-1,3,4-oxadiazole-2-thiole is both leprostatic and tuberculostatic [5]. Some work has been reported on the metal complexes of 5-phenyl-1,3,4-oxadiazole-2-thione [6,7], 5-(4-pyridyl)-1, 3,4-oxadiazole-2-thione [8][9][10][11][12][13], 5-(3-pyridyl)-1,3,4-oxadiazole-2-thione [14], and 5-(2-pyridyl)-1,3,4-oxadiazole-2-thione [15].…”

Section: Introductionmentioning

confidence: 99%

Nickel(II) complexes of 5-phenyl and 5-furan-1,3,4-oxadiazole-2-thiones containing ethylenediamine: synthesis, spectral and X-ray characterization

Singh

Bharty

Kushawaha

et al. 2009

Transition Met Chem

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The products obtained by the reactions of Ni(OAc) 2 Á4H 2 O with Hpot (Hpot = 5-phenyl-1,3,4-oxadiazole-2-thione) and [K(H 2 fchc)] (potassium N 0 -(furan-2-carbonyl) hydrazine carbodithioate), on treatment with excess of ethylenediamine (en), gave mixed ligand complexes [Ni(pot) 2 (en) 2 ] (1) and [Ni(fot) 2 (en) 2 ] (2) (fot = 5-furan-(1,3,4)-oxadiazole-2-thione). These complexes have been characterized with the aid of elemental analyses, IR, magnetic susceptibility and single crystal X-ray studies. In both complexes, the heterocyclic ligand coordinates through oxadiazole nitrogen, and the ligand exists as the thione form. The complexes 1 and 2 have distorted octahedral geometries around the centrosymmetric Ni(II) center with trans oxadiazole ligands. Both complexes show extended hydrogen bonding to give a supramolecular framework.

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Section: Introductionmentioning

confidence: 99%

Nickel(II) complexes of 5-phenyl and 5-furan-1,3,4-oxadiazole-2-thiones containing ethylenediamine: synthesis, spectral and X-ray characterization

Singh

Bharty

Kushawaha

et al. 2009

Transition Met Chem

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“…These include anti-inflammatory (Omar et al, 1996;Palaska et al, 2002;Ramalingum and Sattur, 1990;Raman et al, 1993), hypoglycemic (Girges, 1994;Husain et al, 1986), antianxiety and antidepressant (Harfenist et al, 1996), and antimitotic (Rai and Linganna, 2000) activities. In addition to these, a number of researchers have reported antimicrobial activities (Giri et al, 1976;Mir et al, 1971;Mishra, 1983;Sahin et al, 2002;Singh and Yadav, 1976). Biocidal activities of Schiff bases have also been well established.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Schiff bases of 2-amino-5-aryl-1, 3, 4-oxadiazoles and their evaluation for antimicrobial activities

Mishra

Rajak

Mehta

2005

J. Gen. Appl. Microbiol.

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Twenty Schiff bases of 2-amino-5-aryl-1,3,4-oxadiazoles have been synthesized with different aromatic aldehydes. The structures of the compounds were confirmed by nitrogen analysis, IR and 13 C-NMR spectral data. The antibacterial** properties of the compounds were investigated against Proteus mirabilis (MTCC-425), Pseudomonas aeruginosa (MTCC-424), Bacillus subtilis (MTCC-619) and Staphylococcus aureus (MTCC-96) using the broth dilution method. The most active compounds were 4c (64 m mg/ml), 4f (68 m mg/ml), 4m (64 m mg/ml) and 4q (62 m mg/ml). The antifungal** screening of the compounds were carried out using Aspergillus niger (MTCC-1344) and Candida albicans (MTCC-227) using the broth dilution method. Active compounds were 4g (52 m mg/ml), 4h (56 m mg/ml), 4l (60 m mg/ml), 4m (58 m mg/ml).

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“…It had been reported 23 that heterocycles such as oxadiazoles, thiadiazoles and mercaptotriazoles are themselves important chemotherapeutic agents and exhibit antitubercular, bacteriostatic, hypoglycemic, antiviral, antifungal, antithyroid, carcinostatic and strong herbicidal activity. Some reported mercaptotriazole derivatives showed potent activity 24 more than streptomycin against Candida albicans, whereas derivatives of 5-substituted 1,2,4-oxadiazole-2-thiones are known to possess interesting pharmacodynamic property and some have exhibited remarkable activity 25 against Mycobacterium tuberculosis. Recently, bactericidal and/or fungicidal or antimicrobial activity was reported for oxadiazolidinethiones.…”

Section: Introductionmentioning

confidence: 99%

A new class of dihaloquinolones bearing N'-aldehydoglycosylhydrazides, mercapto-1,2,4-triazole, oxadiazoline and a-amino ester precursors: synthesis and antimicrobial activity

Al‐Soud

Al‐Masoudi

2003

J. Braz. Chem. Soc.

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A reação das quinolonas 6-8 com hidrazina forneceu as hidrazidas 9-11 em rendimentos moderados. A condensação de 9 e 11 com CS 2 /KOH rendeu os sais de potássio 13 e 14, respectivamente, que espontaneamente forneceram as 3-(1,2,4-triazolil)-quinolonas 15 e 16, respectivamente, quando tratadas com hidrazina. A reação de 9 com CS 2 /KOH sob refluxo resultou na 3-(1,2,4-oxadiazolil)-quinolona 17. Alternativamente, 15 foi preparado a partir de 17. O derivado 12, obtido a partir de 10, forneceu o derivado α-amino ester 18 mediante reação com o éster etílico da glicina. O acoplamento de 10 com vários açúcares forneceu as N'-(aldeidoglicosil-quinolona-3-il)carbohidrazidas 19a-e. Os novos compostos sintetizados foram avaliados quanto a sua atividade antibacteriana.Reaction of the quinolones 6-8 with hydrazine afforded the hydrazide 9-11 in moderate yields. Condensation of 9 and 11 with CS 2 /KOH furnished the potassium salts 13 and 14, respectively, which spontaneously afforded the 3-(1,2,4-triazolyl)-quinolones 15 and 16, respectively, on treatment with hydrazine. Reaction of 9 in refluxing CS 2 /KOH gave the 3-(1,2,4-oxadiazolyl)-quinolone 17. Alternatively, 15 was prepared from 17. The azide derivative 12, obtained from 10, furnished the α-amino ester derivative 18, on reaction with the glycine ethyl ester. Coupling of 10 with various sugars gave the N'-aldehydoglycosyl-quinolone-3-yl)carbohydrazides 19a-e. The newly synthesized compounds were screened for their antibacterial activity.

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Antituberculosis agents. Part II. α-[5-(2-Furyl)-1,3,4-oxadiazol-2-yl-thio]acetohydrazide and related compounds

Cited by 5 publications

References 0 publications

Nickel(II) complexes of 5-phenyl and 5-furan-1,3,4-oxadiazole-2-thiones containing ethylenediamine: synthesis, spectral and X-ray characterization

Nickel(II) complexes of 5-phenyl and 5-furan-1,3,4-oxadiazole-2-thiones containing ethylenediamine: synthesis, spectral and X-ray characterization

Synthesis of Schiff bases of 2-amino-5-aryl-1, 3, 4-oxadiazoles and their evaluation for antimicrobial activities

A new class of dihaloquinolones bearing N'-aldehydoglycosylhydrazides, mercapto-1,2,4-triazole, oxadiazoline and a-amino ester precursors: synthesis and antimicrobial activity

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