Synthesis, antimalarial, antileishmanial evaluation, and molecular docking study of some 3-aryl-2-styryl substituted-4(3H)-quinazolinone derivatives
Open Access
- 2 December 2022
- journal article
- research article
- Published by Springer Science and Business Media LLC in BMC Chemistry
- Vol. 16 (1), 1-12
- https://doi.org/10.1186/s13065-022-00903-0
Abstract
Quinazolinones are a diverse group of nitrogen-containing heterocyclic compounds with promising antimalarial and antileishmanial activities. Herein, some 3-aryl-2-styryl substituted-4(3H)-quinazolinones were synthesized via cyclization, condensation, and hydrolysis reactions. 1H NMR, FTIR and elemental microanalysis was used to verify the structures of the synthesized compounds. The in vivo antimalarial and in vitro antileishmanial activities of the target compounds were investigated using mice infected with Plasmodium berghi ANKA and Leishmania donovani strain, respectively. Among the test compounds, 8 and 10 showed better antimalarial activities with percent suppression of 70.01 and 74.18, respectively. In addition, (E)-2-(4-nitrostyryl)-3-phenylquinazolin-4(3H)-one (6) showed promising antileishmanial activity (IC50 = 0.0212 µg/mL). It is two and 150 times more active than the standard drugs amphotericin B deoxycholate (IC50 = 0.0460 µg/mL) and miltefosine (IC 50 = 3.1911 µg/mL), respectively. Its superior in vitro antileishmanial activity was supported by a molecular docking study conducted in the active site of Lm-PTR1. Overall, the synthesized 3-aryl-2-styryl substituted-4(3H)-quinazolinones showed promising antileishmanial and antimalarial activities and are desirable scaffolds for the synthesis of different antileishmanial and antimalarial agents.Keywords
This publication has 48 references indexed in Scilit:
- Synthesis and evaluation of 4-quinazolinone compounds as potential antimalarial agentsEuropean Journal of Medicinal Chemistry, 2010
- Synthesis and antileishmanial and antimicrobial activities of some 2,3-disubstituted 3H-quinazolin-4-onesJournal of Enzyme Inhibition and Medicinal Chemistry, 2010
- Synthesis and antimalarial evaluation of some 4-quinazolinone derivatives based on febrifugineJournal of Advanced Pharmaceutical Technology & Research, 2010
- Synthesis and biological evaluation of febrifugine analogues as potential antimalarial agentsBioorganic & Medicinal Chemistry, 2009
- Rapid fluorescent assay for screening drugs on Leishmania amastigotesJournal of Microbiological Methods, 2008
- Convenient synthesis of some 2‐substituted 4(3H)‐quinazolinone derivativesJournal of Heterocyclic Chemistry, 2006
- Drug Resistance in LeishmaniasisClinical Microbiology Reviews, 2006
- Synthesis, cytotoxicity, and inhibitory effects on tubulin polymerization of a new 3-heterocyclo substituted 2-styrylquinazolinonesEuropean Journal of Medicinal Chemistry, 2004
- Comparison of antimalarial activity of the alkaloidal fraction ofHydrangea macrophylla var.Otaksa leaves with the hot-water extract in ICR mice infected withPlasmodium yoelii 17 XLPhytotherapy Research, 2003
- Human Malaria Parasites in Continuous CultureScience, 1976