A click chemistry approach for the synthesis of mono and bis aryloxy linked coumarinyl triazoles as anti-tubercular agents

Anand, Ashish; Naik, Reshma J.; Revankar, Hrishikesh M.; Kulkarni, Manohar V.; Dixit, Sheshagiri R.; Joshi, Shrinivas D.

doi:10.1016/j.ejmech.2015.10.019

Cited by 71 publications

(14 citation statements)

References 28 publications

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“…The products were characterized by 1D-, 2D- NMR experiments, IR and HRMS, displaying a 1,4-substitution pattern as was expected based our previous experience[18, 37] and by several other reports. [42, 43]…”

Section: Resultsmentioning

confidence: 99%

Antitubercular activity of 1,2,3-triazolyl fatty acid derivatives

Ghiano

Iglesia

Liu

et al. 2017

European Journal of Medicinal Chemistry

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A collection of 1,2,3-triazoles unsaturated fatty acid mimics were efficiently synthesized by click chemistry. The 1,4-disubstituted analogs prepared covered different alkyl chain lengths and triazole positions. The compounds were subsequently tested against Mycobacterium tuberculosis, being most of them active with some of the analogs displaying activity at micromolar concentration. The most potent member of the series has the triazole moiety on the C-2 position with a carbon chain of eight or ten carbon atoms. The 1,5-isomers of the most active analog were significantly less active than the original isomer. The activity of the selected hit was assayed on several clinical MTB multi-drug resistant strains providing the same MIC.

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Section: Resultsmentioning

confidence: 99%

Antitubercular activity of 1,2,3-triazolyl fatty acid derivatives

Ghiano

Iglesia

Liu

et al. 2017

European Journal of Medicinal Chemistry

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“…), as well as their derivatives, occupy an important position in medicinal chemistry ascribed to their fascinating array of pharmacological properties such as antifungal , anti‐proliferative , antitumor , antimalarial , antibacterial , anti‐inflammatory , and anti‐TB activities. In particular, plenty of coumarin/isatin derivatives have been investigated for searching new anti‐TB candidates, and some of them exhibited excellent anti‐TB activity that are exemplified by (+)‐calanolide A . (+)‐Calanolide A , a naturally occurring coumarin‐based derivative, not only is an inhibitor of HIV‐1 reverse transcriptase but also has shown promising potency against MTB.…”

Section: Introductionmentioning

confidence: 99%

1H‐1,2,3‐Triazole‐tethered Isatin–coumarin Hybrids: Design, Synthesis and In Vitro Anti‐mycobacterial Evaluation

Tang

et al. 2018

Journal of Heterocyclic Chem

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A series of novel 1H‐1,2,3‐triazole‐tethered isatin–coumarin hybrids 7a–l integrate three anti‐tuberculosis bioactive substances/pharmacophoric units including coumarin, isatin, and I‐A09 were designed, synthesized, and tested for their in vitro anti‐mycobacterial activity against Mycobacterium smegmatis and Mycobacterium tuberculosis H37Rv as well as cytotoxicity in VERO cell line. The results showed that all hybrids exhibited weak to moderate activity against the tested two strains with minimum inhibitory concentration ranging from 50 to 200 μg/mL.

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“…) as well as their derivatives occupy an important position in medicinal chemistry ascribed to their fascinating array of pharmacological properties. Numerous isatin, 1 H ‐1,2,3‐triazole, and coumarin derivatives have been screened for their anti‐TB activities , and some of them exhibited excellent potency that are exemplified by (+)‐Calanolide A , I‐A09, and hybrid 1 . All (+)‐Calanolide A , I‐A09, and hybrid 1 possess great in vitro and in vivo anti‐TB potency, in particular, (+)‐Calanolide A was not only an inhibitor of HIV‐1 reverse transcriptase but also has shown promising potency against MTB including drug‐resistant strains.…”

Section: Introductionmentioning

confidence: 99%

Propylene‐1H‐1,2,3‐triazole‐4‐methylene‐tethered Isatin‐coumarin Hybrids: Design, Synthesis, and In Vitro Anti‐tubercular Evaluation

Huang

et al. 2018

Journal of Heterocyclic Chem

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A series of novel propylene-1H-1,2,3-triazole-4-methylene-tethered isatin-coumarin hybrids 7a-l that were composed of three anti-tubercular bioactive substances/pharmacophore coumarin, isatin, and I-A09 were designed, synthesized, and assessed for their in vitro anti-tubercular activity against Mycobacterium tuberculosis (MTB) H 37 Rv. In spite of the hybrids were inactive against the tested MTB H 37 Rv, the structure-activity relationship was enriched, and these hybrids may act as an ideal starting point for developing new isatin-coumarin anti-TB candidates with various linkers. Scheme 1. Synthesis of propylene-1H-1,2,3-triazole-4-methylene-tethered isatin-coumarin hybrids 7a-l.

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A click chemistry approach for the synthesis of mono and bis aryloxy linked coumarinyl triazoles as anti-tubercular agents

Cited by 71 publications

References 28 publications

Antitubercular activity of 1,2,3-triazolyl fatty acid derivatives

Antitubercular activity of 1,2,3-triazolyl fatty acid derivatives

1H‐1,2,3‐Triazole‐tethered Isatin–coumarin Hybrids: Design, Synthesis and In Vitro Anti‐mycobacterial Evaluation

Propylene‐1H‐1,2,3‐triazole‐4‐methylene‐tethered Isatin‐coumarin Hybrids: Design, Synthesis, and In Vitro Anti‐tubercular Evaluation

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