Synthesis and antimycobacterial activity of some alkyl [5-(nitroaryl)-1,3,4-thiadiazol-2-ylthio]propionates

Foroumadi, Alireza; Kargar, Zahra; Sakhteman, Amirhossein; Sharifzadeh, Zahra; Feyzmohammadi, Robabeh; Kazemi, Mahnoush; Shafiee, Abbas

doi:10.1016/j.bmcl.2005.11.087

Cited by 66 publications

(28 citation statements)

References 11 publications

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“…Two other reports reveal antituberculosis properties of 1,3,4-thiadiazole scaffolds [B and C] with aryl substitution at C5 position. 29,30) On the other hand, antimycobacterial potency of thioureas such as isoxyl [E] is well documented. A thiophenyl-thiourea derivative [F] has been found as a potent inhibitor of mycobacterial growth (IC 90 =0.23 µg/mL).…”

Section: )mentioning

confidence: 99%

Design, Synthesis, and Molecular Docking Studies of a Conjugated Thiadiazole–Thiourea Scaffold as Antituberculosis Agents

Tatar

Karakuş

Küçükgüzel

et al. 2016

Biological & Pharmaceutical Bulletin

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Section: )mentioning

confidence: 99%

Design, Synthesis, and Molecular Docking Studies of a Conjugated Thiadiazole–Thiourea Scaffold as Antituberculosis Agents

Tatar

Karakuş

Küçükgüzel

et al. 2016

Biological & Pharmaceutical Bulletin

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“…14 The formation of the intermediate was confirmed on the basis of their IR and The compounds 1(a-l) were then treated with chloroacetylchloride to produce 2-chloro-N-[5-(substituted-phenyl [1, 3,4] thiadiazol-2-yl)]-acetamide 2(a-l) and was characterized by an additional singlet of CH2 in 1 H NMR spectra. Further, 2(a-l) was reacted with ammoniumthiocyanate to give cyclized compounds 3(a-l) 15 and the singlet for cyclized CH 2 shows an upfield shift which was then subjected to knoevenagel condensation with benzaldehyde and 3,4 dimethoxybenzaldehyde to yield final compounds as 5-benzylidene 2- 16 Few of the compounds were selected for antimicrobial activity at concentrations of 200 µg/mL and 100 µg/mL.…”

Section: -Benzylidene-2-[{5-(3-nitrophenyl)-[134]-thiadiazol-2-yl}mentioning

confidence: 97%

“…1 The recent literature is enriched with progressive findings about the synthesis of 1,3,4-thiadiazole moiety and their broad spectrum of pharmacological actions such as anti-bacterial, 2 anti-fungal, 2 anti-tubercular, 3 anti-convulsant, 4 anti-inflammatory, 5 analgesic, 5 anti-anxiety, anti-depressant 6 and anti-viral. 7 Thiazolidine-4-one moiety also found to possess diverse biological activities such as anti-microbial 8 , anti-convulsant, 9 antidiarrheal, 10 anti-cancer, 11 K + channel inhibitory, 12 anti-histaminic.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization and Antimicrobial Activity of New Thiadiazole Derivatives

Mullick¹,

Khan²,

Verma³

et al. 2010

Bulletin of the Korean Chemical Society

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A series of thiadiazole derivatives were synthesized with differently substituted benzoic acids which were cyclized to give differently substituted thiazolidin-4-one. Elemental analysis, IR, 1 H NMR, 13C NMR and mass spectral data confirmed the structure of the newly synthesized compounds. The derivatives of these moieties were evaluated for antimicrobial activity. Most of the synthesized compounds showed good antimicrobial activity at 200 and 100 µg/mL. Compounds showed most significant antibacterial activity against gram negative test organism Escherichia coli and most significant antifungal activity against test organisms Aspergillus niger and Candida albicans. It was observed that compounds with OCH3 at 3, 4 position of phenyl ring [5(a-l)] were more potent against microbes as compared to compounds having unsubstituted phenyl ring [4(a-l)].

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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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Synthesis and antimycobacterial activity of some alkyl [5-(nitroaryl)-1,3,4-thiadiazol-2-ylthio]propionates

Cited by 66 publications

References 11 publications

Design, Synthesis, and Molecular Docking Studies of a Conjugated Thiadiazole–Thiourea Scaffold as Antituberculosis Agents

Design, Synthesis, and Molecular Docking Studies of a Conjugated Thiadiazole–Thiourea Scaffold as Antituberculosis Agents

Synthesis, Characterization and Antimicrobial Activity of New Thiadiazole Derivatives

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

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