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Open AccessArticle

Synthesis, Biological Assessment, and Structure Activity Relationship Studies of New Flavanones Embodying Chromene Moieties

1
Department of Chemistry, Taibah University, Madinah 30002, Saudi Arabia
2
Department of Chemistry, University of Prince Edward Island, 550 University Avenue, Charlottetown, PEI C1A 4P3, Canada
3
Department of Chemistry, College of Science, United Arab Emirates University, Al Ain 15551, UAE
*
Author to whom correspondence should be addressed.
Academic Editor: Vincenzo Piccialli
Molecules 2020, 25(3), 544; https://doi.org/10.3390/molecules25030544
Received: 1 December 2019 / Revised: 15 January 2020 / Accepted: 26 January 2020 / Published: 27 January 2020
(This article belongs to the Special Issue New Studies on the Synthesis of Biologically Active Products)
Novel flavanones that incorporate chromene motifs are synthesized via a one-step multicomponent reaction. The structures of the new chromenes are elucidated by using IR, 1H-NMR, 13C-NMR, 1H-1H COSY, HSQC, HMBC, and elemental analysis. The new compounds are screened for their in vitro antimicrobial and cytotoxic activities. The antimicrobial properties are investigated and established against seven human pathogens, employing the agar well diffusion method and the minimum inhibitory concentrations. A majority of the assessed derivatives are found to exhibit significant antimicrobial activities against most bacterial strains, in comparison to standard reference drugs. Moreover, their cytotoxicity is appraised against four different human carcinoma cell lines: human colon carcinoma (HCT-116), human hepatocellular carcinoma (HepG-2), human breast adenocarcinoma (MCF-7), and adenocarcinoma human alveolar basal epithelial cell (A-549). All the desired compounds are subjected to in-silico studies, forecasting their drug likeness, bioactivity, and the absorption, distribution, metabolism, and excretion (ADME) properties prior to their synthetic assembly. The in-silico molecular docking evaluation of all the targeted derivatives is undertaken on gyrase B and the cyclin-dependent kinase. The in-silico predicted outcomes were endorsed by the in vitro studies. View Full-Text
Keywords: flavanone-containing chromene motifs; in-silico studies; antimicrobial examination; cytotoxic behavior; molecular modeling; SAR analysis flavanone-containing chromene motifs; in-silico studies; antimicrobial examination; cytotoxic behavior; molecular modeling; SAR analysis
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MDPI and ACS Style

Assirey, E.; Alsaggaf, A.; Naqvi, A.; Moussa, Z.; Okasha, R.M.; Afifi, T.H.; Abd-El-Aziz, A.S. Synthesis, Biological Assessment, and Structure Activity Relationship Studies of New Flavanones Embodying Chromene Moieties. Molecules 2020, 25, 544.

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