Ionic liquid-promoted one-pot synthesis of thiazole–imidazo[2,1-b][1,3,4]thiadiazole hybrids and their antitubercular activity

Ramprasad, Jurupula; Nayak, Nagabhushana; Dalimba, Udayakumar; Yogeeswari, Perumal; Sriram, Dharmarajan

doi:10.1039/c5md00346f

Cited by 25 publications

(9 citation statements)

References 30 publications

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“…According to in vitro data, compound 77a showed less inhibition than GEQ, and the findings from the docking studies also suggest weaker interaction than GEQ. Dalimba and co-workers in 2016 reported the one-pot synthesis of thiazole-imidazo [2,1-b] [1,3,4]thiadiazole hybrids and investigated their inhibitory action toward tuberculosis (Ramprasad et al, 2016). Compound 79 is the key intermediate, which was synthesized by the reaction of thiosemicarbazone 78 with ketone in the presence of acetyl chloride.…”

Section: Figure 10mentioning

confidence: 99%

Synthetic approaches to potent heterocyclic inhibitors of tuberculosis: A decade review

Dasmahapatra

Chanda

2022

Front. Pharmacol.

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Tuberculosis (TB) continues to be a significant global health concern with about 1.5 million deaths annually. Despite efforts to develop more efficient vaccines, reliable diagnostics, and chemotherapeutics, tuberculosis has become a concern to world health due to HIV, the rapid growth of bacteria that are resistant to treatment, and the recently introduced COVID-19 pandemic. As is well known, advances in synthetic organic chemistry have historically enabled the production of important life-saving medications that have had a tremendous impact on patients’ lives and health all over the world. Small-molecule research as a novel chemical entity for a specific disease target offers in-depth knowledge and potential therapeutic targets. In this viewpoint, we concentrated on the synthesis of a number of heterocycles reported in the previous decade and the screening of their inhibitory action against diverse strains of Mycobacterium tuberculosis. These findings offer specific details on the structure-based activity of several heterocyclic scaffolds backed by their in vitro tests as a promising class of antitubercular medicines, which will be further useful to build effective treatments to prevent this terrible illness.

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Section: Figure 10mentioning

confidence: 99%

Synthetic approaches to potent heterocyclic inhibitors of tuberculosis: A decade review

Dasmahapatra

Chanda

2022

Front. Pharmacol.

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“…The complete experimental, analytical and spectral data along with 1 H-NMR, 13 C-NMR, FT -IR and GC-MS Spectra of this article can be found in the supporting information.…”

Section: Supporting Information Summarymentioning

confidence: 99%

“…Structures of all the newly synthesized compounds were fully characterized by IR, 1 H NMR, 13 C-NMR, Mass and elemental analysis. Synthesis of coumarin and 1-aza-coumarin linked miconazole analogues.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Molecular Modelling Studies of Coumarin and 1‐Aza‐Coumarin Linked Miconazole Analogues and Their Antimicrobial Properties

et al. 2020

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A series of coumarin and 1-Aza coumarin analogues of miconazole(5 a-6 e) were synthesized from 2-bromo-1-(2,4-dichlorophenyl)ethanone and diversification was achieved by synthesizing coumarin-benzimidazole(7 a-7 e) and 1-aza coumarin-benzimidazole(8 a-8 e) hybrids of miconazole and evaluated for in-vitro anti-microbial activities. Among the tested compounds, 8 b-8 e were found to be effective as anti-fungal against C. albicans, C. utilis and C. krusei, with activity compared to that of the standard. Comparative docking studies with mevalonate-5-diphosphatedecarboxylase shows better binding affinity than imidazole counterparts which is primarily attributed to extended π-alkyl interactions facilitated by benzimidazole.

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“…The formed benzoyl ester provided 1,3-diketone in base (pyridine/KOH). The flavones were produced from cyclization of 1,3-ketones under strongly acidic conditions [209]. The flavones were synthesized from various substituted diketones under microwave irradiation in the presence of an ionic liquid catalyst, ethyl ammonium nitrate ([EtNH 3 ][NO 3 ]) without the formation of any side product except water (Scheme 11).…”

Section: Synthesis Of Six-membered O-polyheterocyclesmentioning

confidence: 99%

Ionic liquid assisted synthesis of six-membered oxygen heterocycles

Kaur

2019

SN Appl. Sci.

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Due to special properties of ionic liquids (ILs) like their wide liquid range, good solvating ability, negligible vapour pressure, non-inflammability, environment friendly medium, high thermal stability, easy recycling and rate promoters etc. they are used in organic synthesis. The investigation for replacement of organic solvents in organic synthesis is a growing area of interest due to increasing environmental issues. Therefore, ILs have attracted the attention of chemists and act as catalyst and reaction medium in organic reaction with high activity. There is no doubt that ILs have become a major subject of study for modern chemistry. In comparison to traditional processes the use of ILs resulted in improved, complimentary or alternative selectivities in organic synthesis. The aim of present review is to focus on the applications of ILs for the synthesis of six-membered oxygen heterocycles (pyrans, chromenes, coumarins and dioxanes). Scheme 8 Synthesis of furans and pyran Scheme 27 Synthesis of 4H-benzo[b]pyrans Scheme 28 Synthesis of biscoumarins Scheme 29 Synthesis of 4-methyl-4,5-diphenyl-1,3-dioxane

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Ionic liquid-promoted one-pot synthesis of thiazole–imidazo[2,1-b][1,3,4]thiadiazole hybrids and their antitubercular activity

Abstract: The anti-TB activity of new thiazole–imidazo[2,1-b][1,3,4]thiadiazoles, which are synthesized via one-pot synthesis, is comparable with that of standard drugs.

Cited by 25 publications

References 30 publications

Synthetic approaches to potent heterocyclic inhibitors of tuberculosis: A decade review

Synthetic approaches to potent heterocyclic inhibitors of tuberculosis: A decade review

Synthesis and Molecular Modelling Studies of Coumarin and 1‐Aza‐Coumarin Linked Miconazole Analogues and Their Antimicrobial Properties

Ionic liquid assisted synthesis of six-membered oxygen heterocycles

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