Anticancer and DNA binding studies of potential amino acids based quinazolinone analogs: Synthesis,SAR and molecular docking |
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| Institution: | 1. School of Chemistry, University of Nottingham, University Park, Nottingham NG7 2RD, United Kingdom;2. Department of Chemistry, Quaid-i-Azam University, Islamabad 45320, Pakistan;3. Office of Research, Innovation and Commercialization, University of Gujrat, Gujrat 50700, Pakistan;1. Department of Medicinal Chemistry, National Institute of Pharmaceutical Education and Research (NIPER), Hyderabad, 500 037, India;2. Department of Pharmacology and Toxicology, National Institute of Pharmaceutical Education and Research (NIPER), Hyderabad, 500 037, India;1. Department of Chemistry, Isfahan University of Technology, Isfahan, 84156-83111, Islamic Republic of Iran;2. Department of Medicinal Chemistry, School of Pharmacy and Pharmaceutical Sciences, Isfahan University of Medical Sciences, Isfahan, 81746-73461, Islamic Republic of Iran;1. Department of Organic Chemistry, Faculty of Pharmacy, Al-Azhar University, Cairo, Egypt;2. Department of Pharmaceutical Chemistry, College of Pharmacy, Salman Bin Abdulaziz University, AlKharj, Saudi Arabia;3. Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Al-Azhar University, Cairo, Egypt;4. Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, Riyadh, Saudi Arabia;5. Department of Medicinal Chemistry, Faculty of Pharmacy, University of Mansoura, Mansoura, Egypt |
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| Abstract: | A novel series of amino acids conjugated quinazolinone-Schiff’s bases were synthesized and screened for their in vitro anticancer activity and validated by molecular docking and DNA binding studies. In the present investigations, compounds 32, 33, 34, 41, 42 and 43 showed most potent anticancer activity against tested cancer cell lines and DNA binding study using methyl green comparing to doxorubicin and ethidium bromide as a positive control respectively. The structure-activity relationship (SAR) revealed that the tryptophan and phenylalanine derived electron donating groups (OH and OCH3) favored DNA binding studies and anticancer activity whereas; electron withdrawing groups (Cl, NO2, and F) showed least anticancer activity. The molecular docking study, binding interactions of the most active compounds 33, 34, 42 and 43 stacked with A–T rich regions of the DNA minor groove by surface binding interactions were confirmed. |
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| Keywords: | Quinazolinone Amino acids Anticancer DNA binding Docking study |
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