Synthesis of novel 5-aryl-2-thio-1,3,4-oxadiazoles and the study of their structure–anti-mycobacterial activities

Macaev, Fliur; Rusu, G. G.; Pogrebnoi, Serghei; Gudima, Alexandru; Stingaci, Eugenia; Vlad, L.; Shvets, N.; Kandemi̇rlı, Fatma; Димогло, А. С.; Reynolds, Robert C.

doi:10.1016/j.bmc.2005.05.011

Cited by 122 publications

(65 citation statements)

References 27 publications

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“…Mass spectra (EI-MS) were recorded on JMS-HX-110 spectrometer. 1 H NMR spectra were recorded in MeOD solvent on Bruker spectrometer operating at 500 & 600 MHz. Melting points of synthesized compounds were recorded on Griffin and George meting point apparatus using open capillary tube and were uncorrected.…”

Section: Methodsmentioning

confidence: 99%

“…The increasing interest of researchers has been observed to design the oxadiazole system because of its basic application in the formulation of many drugs with a variety of biological activities [1,2]. 1,3,4-Oxadiazole, the five membered heterocyclic compound having two nitrogen atoms at position 3 and 4, exhibits a broad spectrum of biological activities.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis, Multiparametric Structure Assessment and Biological Evaluation of Some New 1,3,4-Oxadiazoles Containing Piperidine Nucleus

et al. 2017

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With an aim to introduce more biologically active compounds, S-substituted derivatives of 5-[1-(4-nitrophenylsulfonyl)piperidin-4-yl]-1,3,4-oxadiazole-2-thiol (3) were synthesized through four steps. In the first step, ethyl 1-(4-nitrophenylsulfonyl)piperidine-4-carboxylate (1)was synthesized by reacting 4-nitrobenzenesulfonyl chloride (a) and ethyl isonipacotate (b) in basic medium. In the second step, compound 1 and hydrazine monohydrate were converted to corresponding hydrazide (2). In third step, hydrazide (2), CS2 and KOH were refluxed in the presence of MeOH to acquire 5-(1-(4-nitrophenylsulfonyl)piperidin-4-yl)-1,3,4-oxadiazole-2-thiol (3). In the last step, alkyl/aralkylhalides (4a-o) and 3 were made to react in an aprotic polar solvent to get the final compounds, 2-(substitutedthio)-5-[1-(4-nitrophenylsulfonyl)piperidin-4-yl]-1,3,4-oxadiazole (5a-o). The synthesized compounds were structurally confirmed by spectroscopic techniques including 1 H NMR, EIMS and IR. Finally the synthesized compounds were screened for antibacterial activity against five bacterial strains.

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Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis, Multiparametric Structure Assessment and Biological Evaluation of Some New 1,3,4-Oxadiazoles Containing Piperidine Nucleus

et al. 2017

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“…Since compound 3 has a chiral centre, the present study describes the analysis of compound 4 and its analogues on NAT and M. tuberculosis. Structures incorporating the 1,2,4-triazole-3-thione motif and related examples (Macaev et al, 2005;Foroumadi et al, 2006) have been reported recently to have anti-tubercular activity although no mechanism of action has been proposed.…”

Section: Screen Designmentioning

confidence: 99%

Identification of arylamine N-acetyltransferase inhibitors as an approach towards novel anti-tuberculars

et al. 2010

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New anti-tubercular drugs and drug targets are urgently needed to reduce the time for treatment and also to identify agents that will be effective against Mycobacterium tuberculosis persisting intracellularly. Mycobacteria have a unique cell wall. Deletion of the gene for arylamine N-acetyltransferase (NAT) decreases mycobacterial cell wall lipids, particularly the distinctive mycolates, and also increases antibiotic susceptibility and killing within macrophage of Mycobacterium bovis BCG. The nat gene and its associated gene cluster are almost identical in sequence in M. bovis BCG and M. tuberculosis. The gene cluster is essential for intracellular survival of mycobacteria. We have therefore used pure NAT protein for high-throughput screening to identify several classes of small molecules that inhibit NAT activity. Here, we characterize one class of such molecules-triazoles-in relation to its effects on the target enzyme and on both M. bovis BCG and M. tuberculosis. The most potent triazole mimics the effects of deletion of the nat gene on growth, lipid disruption and intracellular survival. We also present the structure-activity relationship between NAT inhibition and effects on mycobacterial growth, and use ligand-protein analysis to give further insight into the structure-activity relationships. We conclude that screening a chemical library with NAT protein yields compounds that have high potential as anti-tubercular agents and that the inhibitors will allow further exploration of the biochemical pathway in which NAT is involved.

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“…1,3,4-Oxadiazoles forms an important class of heterocyclic compounds with broad spectrum of biological activities. Substituted 1,3,4-oxadiazoles have revealed antibacterial 21 , antimycobacterial 22 , antifungal 23 , anti-inflammatory and analgesic [24][25][26] , anticonvulsant 27 , antihyperglycemic 28 , anticancer 29 , anti-HIV-1 30 , and tyrosinase inhibitory activity 31 . 1,2,4-Oxadiazole derivatives have been reported as potent anti-inflammatory agents with selectivity for COX-2 [32][33][34] .…”

Section: Research Articlementioning

confidence: 99%

Synthesis and biological evaluation of 2,5-disubstituted 1,3,4-oxadiazole derivatives with both COX and LOX inhibitory activity

Akhter

Alam

et al. 2011

Journal of Enzyme Inhibition and Medicinal Chemistry

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Synthesis of novel 5-aryl-2-thio-1,3,4-oxadiazoles and the study of their structure–anti-mycobacterial activities

Cited by 122 publications

References 27 publications

Synthesis, Multiparametric Structure Assessment and Biological Evaluation of Some New 1,3,4-Oxadiazoles Containing Piperidine Nucleus

Synthesis, Multiparametric Structure Assessment and Biological Evaluation of Some New 1,3,4-Oxadiazoles Containing Piperidine Nucleus

Identification of arylamine N-acetyltransferase inhibitors as an approach towards novel anti-tuberculars

Synthesis and biological evaluation of 2,5-disubstituted 1,3,4-oxadiazole derivatives with both COX and LOX inhibitory activity

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