First Report on 3‐(3‐oxoaryl) Indole Derivatives as Anticancer Agents: Microwave Assisted Synthesis, <i>In Vitro</i> Screening and Molecular Docking Studies

Patel, Tarun; Gaikwad, Ruchi; Jain, Kavita; Routholla, Ganesh; Bobde, Yamini; Ghosh, Balaram; Das, Kalpataru; Gayen, Shovanlal

doi:10.1002/slct.201900088

Cited by 20 publications

(8 citation statements)

References 36 publications

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“…The molecular docking studies showed a greater degree affinity of these compounds over colchicine in the active site of CBS. [64] 2.17 | Indole-based [1,2,4]triazolo [4,3-a]…”

Section: -Phenyl-1h-indole-2-carbohydrazide Derivativesmentioning

confidence: 99%

Indole derivatives targeting colchicine binding site as potential anticancer agents

Goel

Jaiswal

Jain

2023

Archiv der Pharmazie

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Microtubules are appealing as intracellular targets for anticancer activity due to their importance in cell division. Three important binding sites are present on the tubulin protein: taxane, vinca, and colchicine binding sites (CBS). Many USFDA‐approved drugs such as paclitaxel, ixabepilone, vinblastine, and combretastatin act by altering the dynamics of the microtubules. Additionally, a large number of compounds have been synthesized by medicinal chemists around the globe that target different tubulin binding sites. Although CBS inhibitors have proved their cytotoxic potential, no CBS‐targeting drug had been able to reach the market. Several studies have reported design, synthesis, and biological evaluation of indole derivatives as potential anticancer agents. These compounds have been shown to inhibit cancer cell proliferation, induce apoptosis, and disrupt microtubule formation. Moreover, the binding affinity of these compounds to the CBS has been demonstrated using molecular docking studies and competitive binding assays. The present work has reviewed indole derivatives as potential colchicine‐binding site inhibitors. The structure–activity relationship studies have revealed the crucial pharmacophoric features required for the potent and selective binding of indole derivatives to the CBS. The development of these compounds with improved efficacy and reduced toxicity could potentially lead to the development of novel and effective cancer therapies.

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“…The molecular docking studies showed a greater degree affinity of these compounds over colchicine in the active site of CBS. [64] 2.17 | Indole-based [1,2,4]triazolo [4,3-a]…”

Section: -Phenyl-1h-indole-2-carbohydrazide Derivativesmentioning

confidence: 99%

Indole derivatives targeting colchicine binding site as potential anticancer agents

Goel

Jaiswal

Jain

2023

Archiv der Pharmazie

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“…The reactions were tested with and without the use of solvent, obtaining comparable results ( Kalluraya et al, 2018 ). In the same way, a new protocol, for the synthesis of 3-(3-oxoaryl)indole derivatives, was developed through a microwave-assisted Michael addition of the appropriate chalcone derivatives using commercially available and non-toxic catalyst under solvent-free conditions ( Figure 8C ) ( Patel et al, 2019 ). 1,5-Benzodiazepine derivatives were synthesized with good yields and without the need for column chromatography purification, starting from differently substituted chalcones and 2-aminoaniline dissolved in piperidine and ethanol with the aid of a domestic microwave ( Shetye and Pawar, 2017 ).…”

Section: 1 Ultrasound Chemistrymentioning

confidence: 99%

The green chemistry of chalcones: Valuable sources of privileged core structures for drug discovery

Marotta

Rossi²,

Ibba³

et al. 2022

Front. Chem.

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The sustainable use of resources is essential in all production areas, including pharmaceuticals. However, the aspect of sustainability needs to be taken into consideration not only in the production phase, but during the whole medicinal chemistry drug discovery trajectory. The continuous progress in the fields of green chemistry and the use of artificial intelligence are contributing to the speed and effectiveness of a more sustainable drug discovery pipeline. In this light, here we review the most recent sustainable and green synthetic approaches used for the preparation and derivatization of chalcones, an important class of privileged structures and building blocks used for the preparation of new biologically active compounds with a broad spectrum of potential therapeutic applications. The literature here reported has been retrieved from the SciFinder database using the term “chalcone” as a keyword and filtering the results applying the concept: “green chemistry”, and from the Reaxys database using the keywords “chalcone” and “green”. For both databases the time-frame was 2017–2022. References were manually selected based on relevance.

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“…68 Gayen and co-workers exploited Michael addition reaction and thereby disclosed an effective microwave assisted, solvent-free methodology for 3-(3-oxoaryl)indole derivatives from 2-phenylindole and chalcones in the presence of Lewis catalyst, ZrCl4 (Scheme 38). 69 In the optimized reaction condition, 15 mol% of ZrCl4 was used as the suitable catalyst under microwave radiation power of 280W. The reaction was more facile with chalcones bearing electron-withdrawing group compared to electron-donating ones.…”

Section: Scheme 29mentioning

confidence: 99%

Recent Advances in the Microwave Assisted Synthesis of Benzofuran and Indole Derivatives

Anilkumar¹,

Aneeja²,

Afsina³

2021

HETEROCYCLES

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Microwave (MW) assisted syntheses are environment friendly, efficient, rapid and convenient methodology for the synthesis of organic compounds. Benzene ring fused to a five membered ring containing N or O atom exhibits wide range of biological activities.Benzofuran is present in polymers, pharmaceuticals, and bioactive natural products.Benzofuran is significant as insecticides, herbicides, anti-inflammatory and anti-viral agents.Indoles are well known scaffold showing noteworthy activities like anti-tumor, anti-viral, anti-microbial and anti-oxidant. Indole derivatives are valuable moiety in different therapeutically active drug molecules. On account of the biological significance of benzofuran and indole scaffold, this review describes the recent advances in microwave assisted synthesis of benzofurans and indoles, and covers literature from 2012-2020.

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First Report on 3‐(3‐oxoaryl) Indole Derivatives as Anticancer Agents: Microwave Assisted Synthesis, In Vitro Screening and Molecular Docking Studies

Cited by 20 publications

References 36 publications

Indole derivatives targeting colchicine binding site as potential anticancer agents

Indole derivatives targeting colchicine binding site as potential anticancer agents

The green chemistry of chalcones: Valuable sources of privileged core structures for drug discovery

Recent Advances in the Microwave Assisted Synthesis of Benzofuran and Indole Derivatives

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