Design, Synthesis, Spectral Analysis, In Vitro Anticancer Evaluation and Molecular Docking Studies of Some Fluorescent 4-Amino-2, 3-Dimethyl-1-Phenyl-3-Pyrazolin-5-One, Ampyrone Derivatives

Premnath, D.; Enoch, Israel V.M.V.; Selvakumar, P. Mosae; Indiraleka, M.; Vennila, J. Jannet

doi:10.1007/s12539-015-0138-3

Cited by 14 publications

(9 citation statements)

References 22 publications

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“…Molecular docking, with flexible SP followed by XP, was executed. The grid-based technique, evaluation, and minimization of grid approximation procedure were followed by Premnath et al (2016) and Muthiah et al (2020) . The confirmation of the best interactive molecule with 6WPT protein was concluded based on the G score and number of hydrogen bonds and bonding efficiency and binding energy.…”

Section: Methodsmentioning

confidence: 99%

Synthesis and Cytotoxic Activity of Novel Indole Derivatives and Their in silico Screening on Spike Glycoprotein of SARS-CoV-2

Gobinath

Packialakshmi

Vijayakumar³

et al. 2021

Front. Mol. Biosci.

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This work investigated the interaction of indole with SARS-CoV-2. Indole is widely used as a medical material owing to its astounding biological activities. Indole and its derivatives belong to a significant category of heterocyclic compounds that have been used as a crucial component for several syntheses of medicine. A straightforward one-pot three-component synthesis of indole, coupled with Mannich base derivatives 1a–1j, was synthesized without a catalyst. The products were confirmed by IR, 1H-NMR, 13C-NMR, mass spectra, and elemental analysis. The indole derivatives were tested for cytotoxic activity, using three cancer cell lines and normal cell lines of Human embryonic kidney cell (HEK293), liver cell (LO2), and lung cell (MRC5) by MTT assay using doxorubicin as the standard drug. The result of cytotoxicity indole compound 1c (HepG2, LC50−0.9 μm, MCF−7, LC50−0.55 μm, HeLa, LC50−0.50 μm) was found to have high activity compared with other compounds used for the same purpose. The synthesized derivatives have revealed their safety by exhibiting significantly less cytotoxicity against the normal cell line (HEK-293), (LO2), and (MRC5) with IC50 > 100 μg/ml. Besides, we report an in silico study with spike glycoprotein (SARS-CoV-2-S). The selective molecules of compound 1c exhibited the highest docking score −2.808 (kcal/mol) compared to other compounds. This research work was successful in synthesizing a few compounds with potential as anticancer agents. Furthermore, we have tried to emphasize the anticipated role of indole scaffolds in designing and discovering the much-awaited anti-SARS CoV-2 therapy by exploring the research articles depicting indole moieties as targeting SARS CoV-2 coronavirus.

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Section: Methodsmentioning

confidence: 99%

Synthesis and Cytotoxic Activity of Novel Indole Derivatives and Their in silico Screening on Spike Glycoprotein of SARS-CoV-2

Gobinath

Packialakshmi

Vijayakumar³

et al. 2021

Front. Mol. Biosci.

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“…These strategies expected to disclose the binding affinity of this antimicrobial agent to their respective receptor and their relative orientation inside the receptor and in contact with active site residues. Molecular interaction protocols set up based on Schrödinger (2018-2) program [26,27]. Docking simulation scores were analyzed and detailed in Table 4.…”

Section: Resultsmentioning

confidence: 99%

Domino Multicomponent Approach for the Synthesis of Functionalized Spiro-Indeno[1,2-b]quinoxaline Heterocyclic Hybrids and Their Antimicrobial Activity, Synergistic Effect and Molecular Docking Simulation

et al. 2019

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An expedient synthesis of hitherto unexplored novel hybrid heterocycles comprising dispiropyrrolidine, N-styrylpiperidone and indeno[1,2-b]quinoxaline units has been developed via domino multicomponent 1,3-dipolar cycloaddition strategy employing a new class of azomethine ylide in ionic liquid, 1-butyl-3-methylimidazolium bromide. This domino protocol involves, 1,3-dipolar cycloaddition and concomitant enamine reaction affording the dispiropyrrolidine tethered N-styrylpiperidone hybrid heterocycles in moderate to good yield in a single step. These compounds were evaluated for their antimicrobial activity against bacterial and fungal pathogens, therein compounds 8f, 8h, and 8l displayed significant activity against tested microbial pathogens. The synergistic effect revealed that the combination of compound 8h with streptomycin and vancomycin exhibited potent synergistic activity against E. coli ATCC 25922. In addition, molecular docking simulation has also been studied for the most active compound.

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“…Although administration of this compound is limited due to the agranulocytosis induced by ampyrone as a side effect, there are many reports on its use as a promising anticancer agent [18][19][20]. It is also effective for protection against the oxidative stress in chemotherapeutic agents (III) and also is an important constituent in medical applications [20].…”

Section: Introductionmentioning

confidence: 99%

Novel N‐substituted isatin‐ampyrone Schiff bases as a new class of antiproliferative agents: Design, synthesis, molecular modeling and in vitro cytotoxic activity

Emami

Khabnadideh

Faghih

et al. 2022

Journal of Heterocyclic Chem

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Thirteen novel isatin-ampyrone Schiff bases derivatives were synthesized in only two steps of 70%-90% overall yields. In vitro cytotoxic activity of these new Schiff bases against three human tumor cell lines (MCF-7, A549, and SCOV3) as well as normal breast cell line (MCF-10A) were evaluated by MTT assay. Structure-activity relationship of the tested compounds revealed that chlorine group at C-5 position of the isatin ring significantly increased the cytotoxic activity. This study generally led to introduce a highly active molecule (M 12 ) with IC 50 values of 5.12, 25.5, and 12.9 μΜ, on MCF-7, A549, and SCOV3, respectively. Furthermore, molecular docking studies of the synthesized compounds were also done to investigate their binding modes towards VEGFR-2 and JNK3-MAP kinase as the main targets for isatin-containing anticancer agents. Binding free energy values of the compounds showed positive correlation with their cytotoxic activities. To confirm the docking results, molecular docking simulations of potent compound (M 12 ) against VEGFR-2 and JNK3 MAP kinase were also performed. According to the cytotoxic results and in silico ADMET predictions together, M 12 can be considered as a potent candidate for the future anticancer studies.

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Design, Synthesis, Spectral Analysis, In Vitro Anticancer Evaluation and Molecular Docking Studies of Some Fluorescent 4-Amino-2, 3-Dimethyl-1-Phenyl-3-Pyrazolin-5-One, Ampyrone Derivatives

Cited by 14 publications

References 22 publications

Synthesis and Cytotoxic Activity of Novel Indole Derivatives and Their in silico Screening on Spike Glycoprotein of SARS-CoV-2

Synthesis and Cytotoxic Activity of Novel Indole Derivatives and Their in silico Screening on Spike Glycoprotein of SARS-CoV-2

Domino Multicomponent Approach for the Synthesis of Functionalized Spiro-Indeno[1,2-b]quinoxaline Heterocyclic Hybrids and Their Antimicrobial Activity, Synergistic Effect and Molecular Docking Simulation

Novel N‐substituted isatin‐ampyrone Schiff bases as a new class of antiproliferative agents: Design, synthesis, molecular modeling and in vitro cytotoxic activity

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