Triazole–diindolylmethane conjugates as new antitubercular agents: synthesis, bioevaluation, and molecular docking

Danne, Ashruba B.; Choudhari, Amit; Chakraborty, Shakti; Sarkar, Dhiman; Khedkar, Vijay M.; Shingate, Bapurao B.

doi:10.1039/c8md00055g

Cited by 37 publications

(14 citation statements)

References 72 publications

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“…The in vitro anti-tubercular properties of the triazole-indole hybrid derivatives were evaluated against M. tuberculosis H37Ra in the active and dormant state. 107 The most active compound (78, Fig. 8) showed superior anti-tubercular potency against M. tuberculosis H37Ra dormant, with IC 50 and MIC values of 1 and 3 µg/mL, respectively.…”

Section: Anti-tubercular Activitymentioning

confidence: 98%

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1,2,3-Triazole-containing hybrids as leads in medicinal chemistry: A recent overview

Bozorov

Zhao

Aisa

2019

Bioorganic & Medicinal Chemistry

575

289

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A B S T R A C TThe 1,2,3-triazole ring is a major pharmacophore system among nitrogen-containing heterocycles. These fivemembered heterocyclic motifs with three nitrogen heteroatoms can be prepared easily using 'click' chemistry with copper-or ruthenium-catalysed azide-alkyne cycloaddition reactions. Recently, the 'linker' property of 1,2,3-triazoles was demonstrated, and a novel class of 1,2,3-triazole-containing hybrids and conjugates was synthesised and evaluated as lead compounds for diverse biological targets. These lead compounds have been demonstrated as anticancer, antimicrobial, anti-tubercular, antiviral, antidiabetic, antimalarial, anti-leishmanial, and neuroprotective agents. The present review summarises advances in lead compounds of 1,2,3-triazolecontaining hybrids, conjugates, and their related heterocycles in medicinal chemistry published in 2018. This review will be useful to scientists in research fields of organic synthesis, medicinal chemistry, phytochemistry, and pharmacology. Chemistry: synthesis and properties of the 1,2,3-triazolesThe general synthetic route of 1,2,3-triazoles using click chemistry is described in Scheme 1A. The most popular route to 1,2,3-triazoles is Cu(I)-catalysed Huisgen 1,3-dipolar cycloaddition, which is the https://doi.

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Section: Anti-tubercular Activitymentioning

confidence: 98%

“…Neuroprotective and Alzheimer's disease agents based on 1,2,3-triazole units(105)(106)(107)(108)(109)(110)(111)(112)(113)(114)(115).…”

mentioning

confidence: 99%

1,2,3-Triazole-containing hybrids as leads in medicinal chemistry: A recent overview

Bozorov

Zhao

Aisa

2019

Bioorganic & Medicinal Chemistry

575

289

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“…[ 61 ] Isatin–1,2,3‐triazole hybrids 20 and their bis‐1,2,3‐triazole analogs 21 not only possessed potential in vitro and in vivo anticancer activity (MCF‐7, HeLa, and HEK293 cell lines) but also demonstrated great potency against certain bacteria. [ 62,63 ] The SAR revealed that the introduction of the electron‐withdrawing (trifluoromethyl) group at meta ‐position of the phenyl ring and bromo group at ortho ‐position of the phenyl ring had a great influence on the antibacterial and anticancer activity. Among them, hybrids 20a (MIC: 4.68 μg/ml against P. vulgaris ), 20b (MIC: 2.34 and 4.68 μg/ml against E. coli and B. subtilis ), 21a (MIC: 2.34 and 1.17 μg/ml against S. aureus and B. subtilis ), and 21b (MIC: 1.17 and 2.34 μg/ml against E. coli and B. subtilis ) displayed excellent activity against certain strains, and the activity was comparable to or better than that of streptomycin (MIC: 3.12–6.25 μg/ml).…”

Section: Indole/isatin–azole Hybridsmentioning

confidence: 99%

Indole/isatin‐containing hybrids as potential antibacterial agents

Song

Bian

et al. 2020

Archiv der Pharmazie

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The emergence and worldwide spread of drug-resistant bacteria have already posed a serious threat to human life, creating the urgent need to develop potent and novel antibacterial drug candidates with high efficacy. Indole and isatin (indole-2,3-dione) present a wide structural and mechanistic diversity, so their derivatives possess various pharmacological properties and occupy a salient place in the development of new drugs. Indole/isatin-containing hybrids, which demonstrate a promising activity against a panel of clinically important Gram-positive and Gram-negative bacteria, are privileged scaffolds for the discovery of novel antibacterial candidates. This review, covering articles published between January 2015 and May 2020, focuses on the development and structure-activity relationship (SAR) of indole/isatincontaining hybrids with potential application for fighting bacterial infections, to facilitate further rational design of novel drug candidates.

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“…All compounds were tested against an attenuated strain ( M.tb H37Ra), in both active and dormant state. Compound 19 ( Figure 7 ) proved to be the most potent, with an IC 50 of 0.12 µg mL −1 for nonreplicating bacilli [ 181 ].…”

Section: Targeting Nonreplicating Mtbmentioning

confidence: 99%

Addressing Latent Tuberculosis: New Advances in Mimicking the Disease, Discovering Key Targets, and Designing Hit Compounds

Campaniço

Harjivan

Warner

et al. 2020

IJMS

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Despite being discovered and isolated more than one hundred years ago, tuberculosis (TB) remains a global public health concern arch. Our inability to eradicate this bacillus is strongly related with the growing resistance, low compliance to current drugs, and the capacity of the bacteria to coexist in a state of asymptomatic latency. This last state can be sustained for years or even decades, waiting for a breach in the immune system to become active again. Furthermore, most current therapies are not efficacious against this state, failing to completely clear the infection. Over the years, a series of experimental methods have been developed to mimic the latent state, currently used in drug discovery, both in vitro and in vivo. Most of these methods focus in one specific latency inducing factor, with only a few taking into consideration the complexity of the granuloma and the genomic and proteomic consequences of each physiological factor. A series of targets specifically involved in latency have been studied over the years with promising scaffolds being discovered and explored. Taking in account that solving the latency problem is one of the keys to eradicate the disease, herein we compile current therapies and diagnosis techniques, methods to mimic latency and new targets and compounds in the pipeline of drug discovery.

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Triazole–diindolylmethane conjugates as new antitubercular agents: synthesis, bioevaluation, and molecular docking

Cited by 37 publications

References 72 publications

1,2,3-Triazole-containing hybrids as leads in medicinal chemistry: A recent overview

1,2,3-Triazole-containing hybrids as leads in medicinal chemistry: A recent overview

Indole/isatin‐containing hybrids as potential antibacterial agents

Addressing Latent Tuberculosis: New Advances in Mimicking the Disease, Discovering Key Targets, and Designing Hit Compounds

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