Synthesis, characterization and molecular docking studies of novel 2-amino 3-cyano pyrano[2,3H]chrysin derivatives as potential antimicrobial agents

Ramesh, P.; Reddy, Ch. Sanjeeva; Babu, K. Suresh; Reddy, P. Muralidhar; Rao, V. Srinivasa; Tigulla, Parthasarathy

doi:10.1007/s00044-015-1396-7

Cited by 13 publications

(10 citation statements)

References 38 publications

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“…37 –39 Based on the validation studies using in silico approach, CHR was able to comfortably dock into the active site of SAM-dependent methyltransferase via strong hydrogen bond and hydrophobic interactions. This of course agrees with the observations of Ramesh, 46 where strong hydrogen bonds were formed between the hydroxyl groups on CHR with polar amino acid residues in the binding pocket of some proteins in addition to the strong hydrophobic interactions observed. Inhibition of this enzyme by some bioactive food component such as CHR could be reasonable, thus decrease in generation of reactive methylated arsenic species responsible in arsenic-induced oxidative damage observed in this study.…”

Section: Discussionsupporting

confidence: 92%

The role of molecular modelling strategies in validating the effects of chrysin on sodium arsenite-induced chromosomal and DNA damage

et al. 2018

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Chrysin (CHR) is a food-based bioactive ingredient whereas, sodium arsenite (SA) is one of the major contaminant in drinking water. When ingested, SA contributes to tissue damage due to bioactivation by S-adenosyl methionine (SAM)-dependent methyltransferase. Hence, the needs to nullify this effect by investigating the potentials of CHR on SA-induced genotoxicity in rats. The experiment was divided into two successive stages (ameliorative and preventive, curative studies) for 1 week. Rats were divided into four groups: distilled water, 10mg/kg SA, 10mg/kg CHR and co-administration. In stage 2, the experimental groups were given either CHR or SA for 1 week, and treated in reversed order for additional week. Lipid peroxidation, protein carbonyl and DNA fragmentation in liver, blood brain and bone marrow cells micronucleus were assayed for using standard protocols. Molecular docking of SAM-dependent methyltransferase in the presence of CHR was conducted. CHR significantly ( p < 0.05) decreased the level of lipid peroxidation, protein carbonyls and DNA fragmentation in blood, liver and brain tissues as against group treated with SA. It also significantly ( p<0.05) reduced the level of micronuclei generated in bone marrow cells. The effects of CHR were shown to be ameliorative, preventive and curative in nature. Furthermore, CHR was able to dock (with binding energy of -24.81 kcal/mol and predicted inhibition kinetic constant (Ki) of 0.959 µM) into the active site of SAM-dependent methyltransferase with strong hydrogen bond and hydrophobic interactions. The study might have unravelled the potentials of CHR against SA-induced chromosomal and DNA damage, which might be due to inhibition of SAM-dependent methyltransferase.

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Section: Discussionsupporting

confidence: 92%

The role of molecular modelling strategies in validating the effects of chrysin on sodium arsenite-induced chromosomal and DNA damage

et al. 2018

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“…In continuation to our studies of the synthetic modifications of chrysin and their biological screening [53,54], we herein report the synthesis of new 2-hydroxy-3-chrysino dithiocarbamate derivatives ( 3a – k ). Antimicrobial studies were carried out to find the best drug candidate among the synthesized compounds ( 3a – k ).…”

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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“…Ramesh et al (2015) have paid attention to chrysin, a natural flavone reported exhibiting numerous biological activities, including anticancer activities, anti-inflammatory, antioxidant, and antiallergic. For this reason, they focused on the synthesis of pyrano[2,3 H ]chrysin-type compounds through the multicomponent reaction between chrysin, aromatic aldehydes, and malononitrile [ 65 ]. The synthetic strategy started from chrysin, obtained using the procedure reported in the literature [ 66 , 67 , 68 , 69 ].…”

Section: Synthetic Methods For Highly Active Compounds Against Fox Speciesmentioning

confidence: 99%

A Compendium of the Most Promising Synthesized Organic Compounds against Several Fusarium oxysporum Species: Synthesis, Antifungal Activity, and Perspectives

2021

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Vascular wilt caused by F. oxysporum (FOX) is one of the main limitations of producing several agricultural products worldwide, causing economic losses between 40% and 100%. Various methods have been developed to control this phytopathogen, such as the cultural, biological, and chemical controls, the latter being the most widely used in the agricultural sector. The treatment of this fungus through systemic fungicides, although practical, brings problems because the agrochemical agents used have shown mutagenic effects on the fungus, increasing the pathogen’s resistance. The design and the synthesis of novel synthetic antifungal agents used against FOX have been broadly studied in recent years. This review article presents a compendium of the synthetic methodologies during the last ten years as promissory, which can be used to afford novel and potential agrochemical agents. The revision is addressed from the structural core of the most active synthetic compounds against FOX. The synthetic methodologies implemented strategies based on cyclo condensation reactions, radical cyclization, electrocyclic closures, and carbon–carbon couplings by metal–organic catalysis. This revision contributes significantly to the organic chemistry, supplying novel alternatives for the use of more effective agrochemical agents against F. oxysporum.

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Synthesis, characterization and molecular docking studies of novel 2-amino 3-cyano pyrano[2,3H]chrysin derivatives as potential antimicrobial agents

Cited by 13 publications

References 38 publications

The role of molecular modelling strategies in validating the effects of chrysin on sodium arsenite-induced chromosomal and DNA damage

The role of molecular modelling strategies in validating the effects of chrysin on sodium arsenite-induced chromosomal and DNA damage

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

A Compendium of the Most Promising Synthesized Organic Compounds against Several Fusarium oxysporum Species: Synthesis, Antifungal Activity, and Perspectives

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