Synthesis, antitubercular, antimicrobial activities and molecular docking study of quinoline bearing dihydropyrimidines.

Autor: Desai NC; Division of Medicinal Chemistry, Department of Chemistry, (UGC NON-SAP & DST-FIST Sponsored), Mahatma Gandhi Campus, Maharaja Krishnakumarsinhji Bhavnagar University, Bhavnagar 364 002, Gujarat, India. Electronic address: dnisheeth@rediffmail.com., Kotadiya GM; Division of Medicinal Chemistry, Department of Chemistry, (UGC NON-SAP & DST-FIST Sponsored), Mahatma Gandhi Campus, Maharaja Krishnakumarsinhji Bhavnagar University, Bhavnagar 364 002, Gujarat, India., Jadeja KA; Division of Medicinal Chemistry, Department of Chemistry, (UGC NON-SAP & DST-FIST Sponsored), Mahatma Gandhi Campus, Maharaja Krishnakumarsinhji Bhavnagar University, Bhavnagar 364 002, Gujarat, India., Shah KN; Division of Medicinal Chemistry, Department of Chemistry, (UGC NON-SAP & DST-FIST Sponsored), Mahatma Gandhi Campus, Maharaja Krishnakumarsinhji Bhavnagar University, Bhavnagar 364 002, Gujarat, India., Malani AH; Division of Medicinal Chemistry, Department of Chemistry, (UGC NON-SAP & DST-FIST Sponsored), Mahatma Gandhi Campus, Maharaja Krishnakumarsinhji Bhavnagar University, Bhavnagar 364 002, Gujarat, India., Manga V; Molecular Modeling and Medicinal Chemistry Group, Department of Chemistry, University College of Science, Osmania University, Hyderabad 500007, Telangana, India., Vani T; Molecular Modeling and Medicinal Chemistry Group, Department of Chemistry, University College of Science, Osmania University, Hyderabad 500007, Telangana, India.
Jazyk: angličtina
Zdroj: Bioorganic chemistry [Bioorg Chem] 2021 Oct; Vol. 115, pp. 105173. Date of Electronic Publication: 2021 Jul 15.
DOI: 10.1016/j.bioorg.2021.105173
Abstrakt: In order to develop the antimicrobial and antitubercular agents, we have derived quinoline bearing dihydropyrimidine analogues 5a-o and structures of these compounds were determined by spectroscopic techniques. Further, we have calculated the molecular properties prediction and drug-likeness by Molinspiration property calculation toolkit and MolSoft software, respectively. The most active compound against Mycobacterium tuberculosis (5m, MIC = 0.20 µg/mL) also possessed a maximum drug-likeness model score (0.42). Compounds 5m, 5g and 5k were possessed promising antibacterial activity against tested bacterial species. Compound 5k was the only compound to have eye-catcher antifungal activity. Furthermore, the MTT cytotoxicity results on HeLa cells suggested lower cytotoxicity of biologically active compounds. Supramolecular interactions of the synthesized compounds has been assessed my means of molecular docking studies. Although all the synthesized compounds are showing preferably good interactions with their respective proteins, their binding free energies values suggest that these molecules are preferred for antitubercular activity rather than antimicrobial activity.
(Copyright © 2021 Elsevier Inc. All rights reserved.)
Databáze: MEDLINE
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