Synthesis and biological evaluation of indole-3-carboxamide derivatives as antioxidant agents

Huang, Er-Fang; Zhang, Lan; Xiao, Chuying; Meng, Guangrong; Zhang, Bingqi; Hu, Jianshu; Wan, David Chi Cheong; Meng, Qingguo; Jin, Zhe; Hu, Chun

doi:10.1016/j.cclet.2019.04.044

Cited by 12 publications

(6 citation statements)

References 16 publications

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“…Literature on the N-ethyl substituted indole derivatives with good anti-inflammatory and antioxidant activity is also available. [22,23] Inflammation is a complex reaction of the body to harmful stimuli, i. e., pathogens, damaged cells, and irritants. Inflammation is involved in tissue repair.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis, Molecular Docking and Biological Evaluation of N‐Substituted Indole Derivatives as Potential Anti‐Inflammatory and Antioxidant Agents

Kumari

Singh

2022

Chemistry & Biodiversity

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Novel N-substituted Indole derivatives with various hetero-cyclic moieties were synthesized via an ethyl linker in order to obtain highly potent anti-inflammatory and antioxidant agents. The structure of the obtained chemical compounds was determined using IR, 1 H-NMR, and mass spectroscopy. Molecular docking was used to create selective and efficient COX-2 inhibitors from twelve novel indole derivatives (11a-c, 12a -c, 13a -c, and 14a -c). The compounds 13b and 14b had a high interaction energy, which inhibited the COX-2 enzyme. There is a relationship between anti-inflammatory activity and antioxidants, which is also defined by COX-2 inhibition, according to the mechanism of action. The Swiss ADME online programme was used to determine the drug-like properties of synthesized compounds. Two common and reliable methods were adopted to determine the antioxidant effect. In the DPPH assay, compounds 11a, 11b, and 14b, whereas compounds 11b, 13b, and 14b in the reducing power assay, were the most potent as compared with standard ascorbic acid. To evaluate the antiinflammatory effect at an acute and chronic level, the carrageenan-induced paw edema method along with the formalin-induced inflammation method were used both at low dose and high dose. From the collected results, compounds 13b and 14b were the most potent against acute and chronic inflammation. The results showed that the synthesized compounds are unique as anti-inflammatory and antioxidant agents, and that they could be useful for drug discovery in the future.

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Section: Introductionmentioning

confidence: 99%

“…It would be a great strategy to conjugate hetero‐cyclic moieties with indole to get superior and potent derivatives. Literature on the N ‐ethyl substituted indole derivatives with good anti‐inflammatory and antioxidant activity is also available [22,23] …”

Section: Introductionmentioning

confidence: 99%

Synthesis, Molecular Docking and Biological Evaluation of N‐Substituted Indole Derivatives as Potential Anti‐Inflammatory and Antioxidant Agents

Kumari

Singh

2022

Chemistry & Biodiversity

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“…The indole motifs are one of the most important and abundant nitrogen-containing heterocyclic compounds found in important natural products, various functional molecules, and pharmaceuticals. 1 Indole analogs are very interesting to organic and medicinal chemists due to their biological activities, such as, anti-inflammatory A, 2 antimicrobial B, 3 antioxidant C, 4 and antibacterial D activity (Figure 1). 5…”

Section: Introductionmentioning

confidence: 99%

One-pot, regioselective synthesis of functionalized indole derivatives: a three-component domino reaction of arylamine, arylglyoxal, and 4-hydroxycoumarin or 4-hydroxy-6-methyl-2-pyrone

Mehrabi¹,

Dastouri²,

Asadi³

et al. 2020

Arkivoc

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A metal free, one-pot tandem synthetic routes for functionalized indole derivatives has been established. An efficient three-component reaction was designed with incorporation of Knoevenagel condensation followed by inter-, and intramolecular nucleophilic addition reaction in one-pot under mild condition. The structural diversities of the synthesized compounds have been confirmed spectroscopically, by IR, 1 H-and 13 C NMR, and elemental analyses which agree with the proposed structures.

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“…2 Compound B was found to exhibit significant antioxidant activity against the human neuroblastoma SH-SY5Y cell line. 3 Cephalandole B, isolated from the Taiwanese orchid Cephalanceropsis gracilis , is a natural indole alkaloid. 4…”

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confidence: 99%

“…Indole-3-carboxamides have been recognized as a class of privileged skeletons that are ubiquitous in many natural products, pharmaceuticals, and biologically active compounds (Scheme 1). [1][2][3][4][5] For example, compound A has been identified as a new class of indole-3-carboxamide-based renin inhibitors. 1 A potent and novel reversible P2Y12 receptor antagonist SAR216471 was selected as a preclinical candidate displaying antiplatelet activity.…”

mentioning

confidence: 99%

Palladium-catalyzed carbonylative synthesis of indole-3-carboxamides from 2-ethynylanilines and nitroarenes

Ying

Zhang

et al. 2022

Org. Chem. Front.

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Synthesis and biological evaluation of indole-3-carboxamide derivatives as antioxidant agents

Cited by 12 publications

References 16 publications

Synthesis, Molecular Docking and Biological Evaluation of N‐Substituted Indole Derivatives as Potential Anti‐Inflammatory and Antioxidant Agents

Synthesis, Molecular Docking and Biological Evaluation of N‐Substituted Indole Derivatives as Potential Anti‐Inflammatory and Antioxidant Agents

One-pot, regioselective synthesis of functionalized indole derivatives: a three-component domino reaction of arylamine, arylglyoxal, and 4-hydroxycoumarin or 4-hydroxy-6-methyl-2-pyrone

Palladium-catalyzed carbonylative synthesis of indole-3-carboxamides from 2-ethynylanilines and nitroarenes

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