Synthesis, crystal structure, in-silico ADMET, molecular docking and dynamics simulation studies of thiophene-chalcone analogues

Swamy, S. Nanjunda; Gurumallappa,; Hema, M.K.; Karthik, C.S.; Rajabathar, Jothi Ramalingam; Arokiyaraj, Selvaraj; Lokanath, N.K.; Mallu, P.

doi:10.1016/j.molstruc.2021.131365

Cited by 21 publications

(3 citation statements)

References 33 publications

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“…In order to calculate the pharmacokinetic and physicochemical characteristics during the process of drug discovery, the standardized pharmacokinetic was established. 22 Chemdraw is used to create the structure of the compounds, which is then imported into SMILES through the website's user interface (http:// swissadme.ch/). In the pkCSM online tool, these compounds SMILES were loaded.…”

Section: Toxicity Analysismentioning

confidence: 99%

Design and in silico Prediction of New Methylenedioxyphenyl Derivatives as DNA Topoisomerase II Inhibitors

Rathore¹,

Reddemma²,

Rai³

et al. 2023

Int J. Pharm. Investigation

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Background: Cancer is the world's leading cause of death; more than ten million people die from cancer each year. Rate of morbidity and mortality is increasing day by day. As a result, utilizing chemoinformatics techniques, a novel series of Methylenedioxyphenyl linked with 3,4,5-trimethoxyphenyl/ 2,5-dimethoxyphenyl and pyrimidine has been designed, docked and in-silico predictions of pharmacokinetic, and toxicological parameters. Materials and Methods: A novel class of Methylenedioxyphenyl derivatives was docked by using AutoDock Vina software to reveal the interaction of these derivatives with the active site topoisomerase-II with PBD ID 5GWK. In addition to the above, the ADME studies were performed using Swiss ADME software and the toxicity parameters using the pkCSM online tool. Results: Many derivatives were found to be more active than the standard drug etoposide in docking studies. Binding interaction pattern of selected compounds were studied with the active sites of DNA topoisomerase-II (PBD ID 5GWK) by docking simulation. The results of the screening revealed that compounds B9, B12, B13, B15, B16, B17, B18, B22, and B23 were more active candidates of the series. Conclusion: Molecular docking and ADME/Tox properties of new methylenedioxyphenyl derivatives have been described. As a result, nine compounds from the intended series showed improved docking scores with suitable ADME/Tox properties and satisfactory topo II inhibiting activity, thus these compounds may be the effective inhibitors of topoisomerase IIα enzyme.

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Section: Toxicity Analysismentioning

confidence: 99%

Design and in silico Prediction of New Methylenedioxyphenyl Derivatives as DNA Topoisomerase II Inhibitors

Rathore¹,

Reddemma²,

Rai³

et al. 2023

Int J. Pharm. Investigation

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“…These compounds are characterized by the fusion of a thienyl moiety with a chalcone framework that features an α,β-unsaturated ketone group. Thienyl chalcones possess a diverse array of biological activities, encompassing antimicrobial, 17 anti-inflammatory, 18 antioxidant, 19 and anticancer 20 properties. Consequently, they have garnered substantial attention in the field of drug discovery and development.…”

Section: Introductionmentioning

confidence: 99%

Redefining Chalcone Synthesis: Aldol Adduct Elimination for the Rapid Access to Thienyl Chalcones

Nanjundaswamy,

Chimatahalli Shanthakumar,

Shadakshari

et al. 2024

ACS Omega

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This paper introduces a unique and novel method for synthesizing thienyl chalcones using iron oxide nanoparticles (FeONPs) as a heterogeneous catalyst. It stands out as a rare example in the literature for the synthesis of these chalcones from 1,3-diketones and various aromatic aldehydes. The magnetic FeONPs employed as the catalyst bring several advantages, including their efficiency, affordability, and ecofriendly nature, making them an attractive choice for producing thiophene chalcones. One noteworthy aspect of this methodology is the utilization of mild reaction conditions, which greatly simplify the operational aspects of the reaction. Synthesized chalcones were confirmed through the application of various techniques, proton-NMR, 13 C NMR, mass spectrometry, and single-crystal X-ray diffraction analysis. These analyses provide valuable insights into the chemical compositions and structural characteristics of the synthesized compounds. Significantly, this methodology is reported for the first time in the literature, indicating its novelty and contribution to the field of chalcone synthesis.

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“…The biological profile of chalcone attracted the attention of organic chemists worldwide to design and develop new chalcone derivatives (Rani et al 2019 ). Chalcones exhibited a variety of biological activities including antibacterial (Nanjundaswamy et al 2022 ), antifungal (Lahtchev et al 2008 ), anticancer (Mohamed et al 2012 , 2014 , 2018 , 2022 ; Tantawy et al 2019 ; Fathi et al 2021 ; Srilaxmi et al 2021 ; Helmy et al 2021 ; WalyEldeen et al 2022 , 2023 ; Kamel et al 2022 ; Sroor et al 2022 ) anti-inflammatory (Rojas et al 2003 ), antimalarial (Larsen et al 2005 ), and antiviral (Cheenpracha et al 2006 ). The mechanism of action for chalcones can be act via the α,β-unsaturated carbonyl moiety as Michael acceptor, thioredoxin reductase, and inhibition of microtubule formation (Menezes and Diederich 2019 ).…”

Section: Introductionmentioning

confidence: 99%

Novel eco-friendly [1,2,4]triazolo[3,4-a]isoquinoline chalcone derivatives efficiency against fungal deterioration of ancient Egyptian mummy cartonnage, Egypt

et al. 2023

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Fungal deterioration is one of the major factors that significantly contribute to mummy cartonnage damage. Isolation and molecular identification of thirteen fungal species contributing to the deterioration of ancient Egyptian mummy cartonnage located in El-Lahun regions, Fayoum government, Egypt was performed. The most dominant deteriorated fungal species are Aspergillus flavus (25.70%), Aspergillus terreus (16.76%), followed by A. niger (13.97%). A newly synthesized series of tetrahydro-[1,2,4]triazolo[3,4-a]isoquinoline chalcone derivatives were synthesized and evaluated for their antifungal activities in vitro against the isolated deteriorated fungal species (Aspergillus flavus, A. niger, A. terreus, Athelia bombacina, Aureobasidium iranianum, Byssochlamys spectabilis, Cladosporium cladosporioides, C. ramotenellum, Penicillium crustosum, P. polonicum, Talaromyces atroroseus, T. minioluteus and T. purpureogenus). The most efficient chalcone derivatives are new chalcone derivative numbers 9 with minimum inhibitory concentration (MIC) ranging from 1 to 3 mg/mL followed by chalcone derivatives number 5 with MIC ranging from 1 to 4 mg/mL.

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Synthesis, crystal structure, in-silico ADMET, molecular docking and dynamics simulation studies of thiophene-chalcone analogues

Cited by 21 publications

References 33 publications

Design and in silico Prediction of New Methylenedioxyphenyl Derivatives as DNA Topoisomerase II Inhibitors

Design and in silico Prediction of New Methylenedioxyphenyl Derivatives as DNA Topoisomerase II Inhibitors

Redefining Chalcone Synthesis: Aldol Adduct Elimination for the Rapid Access to Thienyl Chalcones

Novel eco-friendly [1,2,4]triazolo[3,4-a]isoquinoline chalcone derivatives efficiency against fungal deterioration of ancient Egyptian mummy cartonnage, Egypt

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