Synthesis of new chromeno-carbamodithioate derivatives and preliminary evaluation of their antioxidant activity and molecular docking studies

Bandari, Sampath Kumar; Kammari, Bal Raju; Madda, Jyothi; Nagaiah, K.; Lakkadi, Arunapriya; Vuppala, Srimai; Tigulla, Parthasarathy

doi:10.1016/j.bmcl.2017.01.047

Cited by 13 publications

(4 citation statements)

References 28 publications

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“…They can undergo regioselective ring opening from the less hindered terminal carbon side of the epoxide ring with a wide variety of nucleophiles by SN 2 reaction. The dithiocarbamate nucleophiles generated in situ from CS 2 and amines open the epoxide ring from the terminal carbon side [39,40,41] to afford 2-hydroxy dithiocarbamates, which are found to have a wide variety of applications in organic synthesis [42,43,44,45], pharmaceuticals [46,47,48,49], and agriculture [50,51,52].…”

Section: Introductionmentioning

confidence: 99%

Molecular Design, Synthesis, and Biological Evaluation of 2-Hydroxy-3-Chrysino Dithiocarbamate Derivatives

et al. 2019

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A series of 2-hydroxy-3-chrysino dithiocarbamate derivatives (3a–k) were designed, synthesized, and characterized for their structure determination by 1H NMR, 13C NMR, and HRMS (ESI) spectral data. They were screened for their in vitro biological activities against a panel of selected bacterial and fungal strains. These antimicrobial studies indicate that some of the analogues manifested significant activity compared to standard drugs. Among the synthetic analogues (3a–k), compounds 3d, 3f, and 3j exhibited very good antibacterial activity and compounds 3d, 3f, and 3h showed very good antifungal activity compared to the standard drugs penicillin and itrazole, respectively. The compounds 3e, 3g, and 3h showed moderate antibacterial activity and the compounds 3j and 3k showed moderate antifungal activity. Molecular docking studies were performed and the experimental antimicrobial screening results were also correlated with the binding energy values obtained by molecular docking. The synthesized chrysin analogues (3a–k) have obeyed Lipinski’s “rule of five” and have drug-likeness.

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Section: Introductionmentioning

confidence: 99%

Molecular Design, Synthesis, and Biological Evaluation of 2-Hydroxy-3-Chrysino Dithiocarbamate Derivatives

et al. 2019

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“…Molecular docking has aided in the elucidation of the antioxidant mechanism of compounds submitted to biological tests such as new chromeno-carbamodithioates derivatives. These compounds have been evaluated for their antioxidant activity in the cyclooxygenase-2 enzyme, using the GOLD program to assess the full range of ligand flexibility and the rotational flexibility of selected receptor hydrogens, and the Autodock 4.0 program to check out the binding free energy and inhibition constant (Ki) concerning the interaction of ligands with the receptor [ 8 ]. Molecular docking study at the PPARα/γ receptor has been used to evaluate the agonist and the antioxidant activity of a novel structural class of coumarin-chalcone fibrates using AutoDock 4.2.6 program [ 9 ].…”

Section: Introductionmentioning

confidence: 99%

An In Silico Study of the Antioxidant Ability for Two Caffeine Analogs Using Molecular Docking and Quantum Chemical Methods

et al. 2018

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The antioxidant activity of molecules constitutes an important factor for the regulation of redox homeostasis and reduction of the oxidative stress. Cells affected by oxidative stress can undergo genetic alteration, causing structural changes and promoting the onset of chronic diseases, such as cancer. We have performed an in silico study to evaluate the antioxidant potential of two molecules of the zinc database: ZINC08706191 (Z91) and ZINC08992920 (Z20). Molecular docking, quantum chemical calculations (HF/6-31G**) and Pearson’s correlation have been performed. Molecular docking results of Z91 and Z20 showed both the lower binding affinity (BA) and inhibition constant (Ki) values for the receptor-ligand interactions in the three tested enzymes (cytochrome P450—CP450, myeloperoxidase—MP and NADPH oxidase—NO) than the control molecules (5-fluorouracil—FLU, melatonin—MEL and dextromethorphan—DEX, for each receptor respectively). Molecular descriptors were correlated with Ki and strong correlations were observed for the CP450, MP and NO receptors. These and other results attest the significant antioxidant ability of Z91 and Z20, that may be indicated for further analyses in relation to the control of oxidative stress and as possible antioxidant agents to be used in the pharmaceutical industry.

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“…396 Various 2,3-dimethyl-4H-chromen-4-ones were readily available through one-pot Kostanecki-Robinson cyclization protocol, reacting 2 0 -hydroxypropiophenones as starting materials with acetic anhydride and sodium acetate under reflux, subsequent treatment with anhydrous triethylamine and the mixture was heated overnight at 115 °C and finally acidification with hydrochloric acid at 40 °C. [397][398][399][400] Ethyl 8-methoxy-3methyl-4-oxo-4H-chromen-2-carboxylate was prepared by microwaveassisted condensation reaction of 2 0 -hydroxy-3 0 -methoxypropiophenone with ethyl chlorooxoacetate in the presence of triethylamine in dichloromethane at 100 °C in a reproducible but rather moderate yield. 400 Moreover, ethyl 3-aryl-4-oxo-4H-chromen-2-carboxylates were prepared from the reaction of 2-aryl-1-(2-hydroxaryl)ethan-1-ones with ethyl chlorooxoacetate in pyridine at 0 °C and subsequent acidification with a 1:1 mixture of 1 N hydrochloric acid:ethanol, under refluxing conditions (Scheme 70).…”

Section: Through Condensation With Carbonyl Compoundsmentioning

confidence: 99%

Recent advances in the synthesis of 4H-chromen-4-ones (2012 − 2021)

Santos

Silva

2022

Advances in Heterocyclic Chemistry

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Synthesis of new chromeno-carbamodithioate derivatives and preliminary evaluation of their antioxidant activity and molecular docking studies

Cited by 13 publications

References 28 publications

Molecular Design, Synthesis, and Biological Evaluation of 2-Hydroxy-3-Chrysino Dithiocarbamate Derivatives

Molecular Design, Synthesis, and Biological Evaluation of 2-Hydroxy-3-Chrysino Dithiocarbamate Derivatives

An In Silico Study of the Antioxidant Ability for Two Caffeine Analogs Using Molecular Docking and Quantum Chemical Methods

Recent advances in the synthesis of 4H-chromen-4-ones (2012 − 2021)

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