Synthesis, Characterization, Biocomputational Modeling and Antibacterial Study of Novel Pyran Based on 8-Hydroxyquinolin
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RESEARCH ARTICLE-CHEMISTRY
Synthesis, Characterization, Biocomputational Modeling and Antibacterial Study of Novel Pyran Based on 8-Hydroxyquinoline M. Rbaa1 · A. Hichar2 · P. Dohare3 · El H. Anouar4 · Y. Lakhrissi1 · B. Lakhrissi1 · M. Berredjem5 · F. Almalki6 · V. Rastija7 · M. Rajabi8 · T. Ben Hadda6,9 · A. Zarrouk10 Received: 11 July 2020 / Accepted: 26 October 2020 © King Fahd University of Petroleum & Minerals 2020
Abstract In this work, we report the synthesis of a new family of organic compounds based on 8-hydroxyquinoline using a simple and efficient method. The synthesized 8-hydroxyquinoline derivatives were characterized by analysis of 1 H and 13 C NMR, FT-IR spectral data and elemental analysis (EA). Their antibacterial activity is tested against Gram-positive strains [S. aureus (ATCC29213), V. parahaemolyticus (ATCC17802)] and Gram negative [E. coli (ATCC35218), P. aeruginosa (ATCC27853)] by the use of the agar diffusion technique. The obtained results showed that the synthesized 8-hydroxyquinoline derivatives have a potent antibacterial activity against the tested strains compared to Norfloxacin as a standard antibiotic. The results also reveal the effectiveness of these compounds at low concentrations, with a MIC of 1.00 μg/ml for compound 4a. Their antibacterial activity has also been optimized by bioinformatics studies (POM analyses). The experimental results are in relatively good agreement with the corresponding theoretical ones. Keywords 8-Hydroxyquinoline · Synthesis · Antibacterial activity · Drug design · POM analyses
1 Introduction Electronic supplementary material The online version of this article (https://doi.org/10.1007/s13369-020-05089-y) contains supplementary material, which is available to authorized users.
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M. Rbaa [email protected] A. Zarrouk [email protected]
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Laboratory of Organic Chemistry, Catalysis and Environment, Faculty of Sciences, Ibn Tofail University, PO Box 133, 14000 Kenitra, Morocco Faculty of Science, Department of Biology, Laboratory of Nutrition, Health and Environment, Ibn Tofaïl University, B.P. 133, 14000 Kenitra, Morocco Department of Chemistry, Indian Institute of Technology (BHU), Varanasi 221005, India Department of Chemistry, College of Science and Humanities Studies in Al-Kharj, Prince Sattam Bin Abdulaziz University, Al-Kharj 11942, Saudi Arabia Laboratory of Applied Organic Chemistry LCOA, Synthesis of Biomolecules and Molecular Modelling Group, Badji-Mokhtar - Annaba University, Box 12, 23000 Annaba, Algeria
The increase in products resulting from industrial, agricultural and domestic activities is causing the creation of new bacterial pathogens [1]. The use of antibiotics against bacterial strains causes bacterial resistance to these antibiotics if they are used in excess or inappropriately, so it is important to seek out, and discover new organically synthesized compounds that might be more effective against all these bacteria. Organic synthesis is one of the concerns of organic chemists 6
Department of Pharmaceutical C
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