SAR studies on 1,2,4-triazolo[3,4-b][1,3,4]thiadiazoles as inhibitors of Mtb shikimate dehydrogenase for the development of novel antitubercular agents

Li, Ziqiang; Liu, Yishuang; Xiu-juan, Bai; Deng, Qi; Wang, Juxian; Zhang, Guoning; Xiao, Chunling; Mei, Yaning; Wang, Yucheng

doi:10.1039/c5ra19334f

Cited by 22 publications

(14 citation statements)

References 22 publications

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“…Although the triazolothiadiazole scaffold is known in the anti-infective − and anticancer literature, − we were initially concerned about its chemical stability. Compounds were found to be stable after several months as 10 mM DMSO solutions and in biochemical assay buffer (analyzed by HPLC–MS, under mildly acidic and basic mobile phase conditions, data not shown).…”

Section: Resultsmentioning

confidence: 99%

Identification of Triazolothiadiazoles as Potent Inhibitors of the dCTP Pyrophosphatase 1

et al. 2017

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The dCTP pyrophosphatase 1 (dCTPase) is involved in the regulation of the cellular dNTP pool and has been linked to cancer progression. Here we report on the discovery of a series of 3,6-disubstituted triazolothiadiazoles as potent dCTPase inhibitors. Compounds 16 and 18 display good correlation between enzymatic inhibition and target engagement, together with efficacy in a cellular synergy model, deeming them as a promising starting point for hit-to-lead development.

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Section: Resultsmentioning

confidence: 99%

Identification of Triazolothiadiazoles as Potent Inhibitors of the dCTP Pyrophosphatase 1

et al. 2017

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“…Benzohydrazide (12) : Following procedure 2 with DBU (228 mg, 1.5 mmol, 1.0 equiv.) and hydrazine monohydrate (150 mg, 3.0 mmol, 2.0 equiv.)…”

Section: Methodsmentioning

confidence: 99%

Metal‐Free Decarboxylative Trichlorination of Alkynyl Carboxylic Acids: Synthesis of Trichloromethyl Ketones

et al. 2017

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2,2,2-Trichloroacetophenone derivatives were synthesized via decarboxylative trichlorination from arylpropiolic acids and trichloroisocyanuric acid (TCCA). Ther eactionw as performed in the presence of water at room temperature,a nd the desired products were obtained in good yields.T he reaction showedg oodf unctional group tolerance towards halide,c yano,n itro,k etone,e ster anda ldehyde groups.I na ddition,t he 2,2,2-trichloroacetophenone derivatives were readily transformed into esters, amides,a nd hydrazides.B asedo ne xperiments with H 2 18 O( water-18 O), we proposedacationic reaction pathwaya st he mechanism and suggested two different pathways for producing aryl-and alkyl-substitutedpropiolic acids.

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“…38 ) with structural modifications at C-3 and C-6 positions of fused system were reported to inhibit the growth of Mtb H 37 Rv, MDR-TB (isoniazid and rifampin resistant strains) and DR-TB (rifampin resistant strains) by Li et al. [ 163 , 164 ]. SAR revealed that the electron-withdrawing groups at para position of the phenyl ring at the 3-position and p -bromophenoxymethyl group at the 6-position on the triazolothiadiazole 184 displayed significant enhancement in potency.…”

Section: Biological Activities Of 124-triazole Derivativesmentioning

confidence: 99%

An insight on medicinal attributes of 1,2,4-triazoles

Aggarwal

Sumran²

2020

European Journal of Medicinal Chemistry

196

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The present review aims to summarize the pharmacological profile of 1,2,4-triazole, one of the emerging privileged scaffold, as antifungal, antibacterial, anticancer, anticonvulsant, antituberculosis, antiviral, antiparasitic, analgesic and anti-inflammatory agents, etc. along with structure-activity relationship. The comprehensive compilation of work carried out in the last decade on 1,2,4-triazole nucleus will provide inevitable scope for researchers for the advancement of novel potential drug candidates having better efficacy and selectivity.

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SAR studies on 1,2,4-triazolo[3,4-b][1,3,4]thiadiazoles as inhibitors of Mtb shikimate dehydrogenase for the development of novel antitubercular agents

Abstract: Triazolothiadiazoles are potent antitubercular agents with modest inhibitory for Mt SD and without appreciable cytotoxicity.

Cited by 22 publications

References 22 publications

Identification of Triazolothiadiazoles as Potent Inhibitors of the dCTP Pyrophosphatase 1

Identification of Triazolothiadiazoles as Potent Inhibitors of the dCTP Pyrophosphatase 1

Metal‐Free Decarboxylative Trichlorination of Alkynyl Carboxylic Acids: Synthesis of Trichloromethyl Ketones

An insight on medicinal attributes of 1,2,4-triazoles

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