Construction, molecular docking, antimicrobial and antioxidant activity of some novel 3-substitued indole derivatives using 3-Acetyl indole

Al-Khaldi, Alanoud; Ghoneim, Amira A.; Elsherif, Mervat A.; Elbargisy, Rehab Mohammed; Ghanem, Heba Bassiony; Zafar, Rehman

doi:10.1016/j.jscs.2021.101360

Cited by 5 publications

(3 citation statements)

References 18 publications

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“…It revealed four singlet signals at δ = 2.26, 2.34, 2.41, and 2.48 ppm attributed to methyl groups on thiazoles and hydrazone moieties, , respectively. H-2 and (NH) exchangeable protons of the indole ring were resonated at δ = 8.26 and 11.85 ppm, respectively. In the mass spectrum, the molecular ion peak of 7a was recorded at m / z 527 which acquiesced with the molecular weight of the assigned structure.…”

Section: Resultsmentioning

confidence: 99%

Synthesis, Biological Evaluation, and Molecular Docking of Novel Azolylhydrazonothiazoles as Potential Anticancer Agents

Al-Humaidi,

Gomha,

Riyadh

et al. 2023

ACS Omega

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A novel set of thiazolylhydrazonothiazoles bearing an indole moiety were synthesized by subjection reactions of carbothioamide derivative and hydrazonoyl chlorides (or α-haloketones). The cytotoxicity of the synthesized compounds was evaluated against the colon carcinoma cell line (HCT-116), liver carcinoma cell line (HepG2), and breast carcinoma cell line (MDA-MB-231), and demonstrated encouraging activity. Furthermore, when representative products were assessed for toxicity against normal cells, minimal toxic effects were observed, indicating their potential safety for use in pharmacological studies. The mechanism of action of the tested products, as inhibitors of the epidermal growth factor receptor tyrosine kinase domain (EGFR TK) protein, was suggested through docking studies that assessed their binding scores and modes, in comparison to a reference standard (W19), thus endorsing their anticancer activity.

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Section: Resultsmentioning

confidence: 99%

Synthesis, Biological Evaluation, and Molecular Docking of Novel Azolylhydrazonothiazoles as Potential Anticancer Agents

Al-Humaidi,

Gomha,

Riyadh

et al. 2023

ACS Omega

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“…Heterocyclic substitution may cause changes in the degree of ionization of compounds in physiological pH, resulting in variations of basicity and lipophilicity . Biological activities and pharmaceutical uses attributed to heterocycles as part of active molecules include antitubercular, analgesic, antipyretic, anti-inflammatory, antiplatelet, anti-HIV, antagonist, CNS depressant, antifungal, antibacterial, antioxidant, and anticancer activities. – Amid the many prominent anticancer scaffolds that have replaced one or both aromatic rings in organic chalcones include diazepines, indoles, triazoles, thiazoles, thiophenes, and imidazolones, among many others. – These compounds exhibited IC 50 values ranging from 0.16 to 11 μM toward breast, lung, colon, cervix, leukemia, and cancer cell lines ,– Including ferrocene in the chalcone moiety has been explored toward the search for novel anticancer agents. Among those studied are furan, pyrazole, and piperazine-bearing ferrocene–chalcone hybrids with IC 50 values as low as 1 μM toward MDA-MB-231. – This study aims to further broaden the library of ferrocene–chalcone hybrids by synthesizing 15 novel compounds bearing azoles, pyrimidines, pyrrole, and indole moieties.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Novel Heterocyclic Ferrocenyl Chalcones and Their Biological Evaluation

Alsina-Sánchez,

Montalvo-Vázquez,

Grafals-Ruiz

et al. 2023

ACS Omega

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Breast cancer is currently the most commonly diagnosed cancer, with 287,850 new cases estimated for 2022 as reported by the American Cancer Society. Therefore, finding an effective treatment for this disease is imperative. Chalcones are α,β-unsaturated systems found in nature. These compounds have shown a wide array of biological activities, making them popular synthetic targets. Chalcones consist of two aromatic substituents connected by an enone bridge; this arrangement allows for a large number of derivatives. Given the biological relevance of these compounds, novel ferrocene-heterocycle-containing chalcones were synthesized and characterized based on a hybrid drug design approach. These heterocycles included thiophene, pyrimidine, thiazolyl, and indole groups. Fourteen novel heterocyclic ferrocenyl chalcones were synthesized and characterized. Herein, we also report their cytotoxicity against triple-negative breast cancer cell lines MDA-MB-231 and 4T1 and the noncancer lung cell line MRC-5. System 3 ferrocenyl chalcones displayed superior anticancer properties compared to their system 1 analogues. System 3 chalcones bearing five-membered heterocyclic substituents (thiophene, pyrazole, pyrrole, and pyrimidine) were the most active toward the MDA-MB-231 cancer cell line with IC 50 values from 6.59 to 12.51 μM. Cytotoxicity of the evaluated compounds in the 4T1 cell line exhibited IC 50 values from 13.23 to 213.7 μM. System 3 pyrazole chalcone had consistent toxicity toward both cell lines (IC 50 ∼ 13 μM) as well as promising selectivity relative to the noncancer MRC-5 control. Antioxidant activity was also evaluated, where, contrary to anticancer capabilities, system 1 ferrocenyl chalcones were superior to their system 3 analogues. Antioxidant activity comparable to that of ascorbic acid was observed for thiophene-bearing ferrocenyl chalcone with EC 50 = 31 μM.

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“…[14,15] In recent literature, 5-substituted indole derivatives have also been described as good antioxidant and anti-inflammatory agents. [16] Various other key heterocyclic moieties have also made a significant contribution to the prevention of comparable diseases. [17,18] The fantastic biological roles of N-alkyl substituted indoles, morpholines, imidazoles, piperidine derivatives, and so on are highlighted in various works.…”

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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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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Construction, molecular docking, antimicrobial and antioxidant activity of some novel 3-substitued indole derivatives using 3-Acetyl indole

Cited by 5 publications

References 18 publications

Synthesis, Biological Evaluation, and Molecular Docking of Novel Azolylhydrazonothiazoles as Potential Anticancer Agents

Synthesis, Biological Evaluation, and Molecular Docking of Novel Azolylhydrazonothiazoles as Potential Anticancer Agents

Synthesis of Novel Heterocyclic Ferrocenyl Chalcones and Their Biological Evaluation

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

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