Antibacterial activity of newer Quinazolin-4(3H)-one derivatives

Abstract

Event Abstract Back to Event Antibacterial activity of newer Quinazolin-4(3H)-one derivatives Gopal Natesan1*, Appalaraju Velaga1, Nelycia Su Yean Tze1 and Soon An Nie1 1 Faculty of Pharmacy, Mahsa University, Malaysia Background Heterocyclic chemistry has gained remarkable attention recently due to its pharmacological diversity in medicinal chemistry research. Quinazolin-4(3H)-one pharmacophore is one of the most important heterocycles, which possess wide spectrum of biological properties like antimicrobial, anticonvulsant, anti-inflammatory and anticancer activities. Hence, this pharmacophore has been considered as a privileged structure to introduce many bioactive moieties to its nucleus for creating new prospective medicinal agents. Methods Quinazolinone derivatives were synthesized by reacting anthranilic acid with benzoyl chloride/4-methoxy benzoyl chloride followed by condensation with hydrazine hydrate, which was further subjected to Schiff base reaction with the different aromatic/heterocyclic aldehydes. The structures of all newly synthesized compounds were characterized by using FT-IR, H1 NMR Spectra. Ten (10) final compounds and two (2) intermediates were evaluated for their antibacterial property against gram-positive (Staphylococcus aureus ATCC 29213 and Bacillus cereus ATCC11778) and gram-negative bacteria (Escherichia coli ATCC 25922 and Pseudomonas aeruginosa ATCC 27853) using agar well diffusion method at a concentration of 50 µg/ml and 100 µg/ml using Norfloxacin as reference drug. Results The parent 2-phenyl-3-amino quinazoline-4(3H)-one (IIa) showed moderate activity against both gram-positive bacteria and gram-negative bacteria whereas substitution of –OCH3 in the phenyl position at the 2nd position of quinazolinone reduces the activity against both strains. The same pattern of the results has been observed among the final Schiff bases. Among the Schiff bases, increase in substitution of –OCH3 group at benzylidene nucleus alters the antibacterial activity. Lower number of methoxy groups exhibited moderate activity against all microorganism whereas increase in number of methoxy group substitution at benzyl-inde nucleus decreases the antibacterial activity against B. cereus and P. aeruginosa and diminishes the activity against S. aureus and E. coli. On the other hand, substitution of a heteryl group at the aldimine in 3-amino quinazolinone pharmacophore significantly increases the antibacterial activity against all the tested bacterial pathogens. Conclusion From the present study, it has been concluded that 2-Phenyl-3-[1-(furfurylidene amino)]-quinazolin-4-(3H)-one (IIIe) showed superior activity among the synthesized compounds. Replacement of benzene ring with heteryl group or substitution of electron donating group in the benzylidene nucleus displayed good antibacterial effects. Keywords: Quinazolin-4(3H)-one, Schiff base, Antibacterial, benzoxazinone, Benzylidene Conference: International Conference on Drug Discovery and Translational Medicine 2018 (ICDDTM '18) “Seizing Opportunities and Addressing Challenges of Precision Medicine”, Putrajaya, Malaysia, 3 Dec - 5 Feb, 2019. Presentation Type: Poster Presentation Topic: Infectious diseases Citation: Natesan G, Velaga A, Yean Tze N and An Nie S (2019). Antibacterial activity of newer Quinazolin-4(3H)-one derivatives. Front. Pharmacol. Conference Abstract: International Conference on Drug Discovery and Translational Medicine 2018 (ICDDTM '18) “Seizing Opportunities and Addressing Challenges of Precision Medicine”. doi: 10.3389/conf.fphar.2018.63.00101 Copyright: The abstracts in this collection have not been subject to any Frontiers peer review or checks, and are not endorsed by Frontiers. They are made available through the Frontiers publishing platform as a service to conference organizers and presenters. The copyright in the individual abstracts is owned by the author of each abstract or his/her employer unless otherwise stated. Each abstract, as well as the collection of abstracts, are published under a Creative Commons CC-BY 4.0 (attribution) licence (https://creativecommons.org/licenses/by/4.0/) and may thus be reproduced, translated, adapted and be the subject of derivative works provided the authors and Frontiers are attributed. For Frontiers’ terms and conditions please see https://www.frontiersin.org/legal/terms-and-conditions. Received: 16 Oct 2018; Published Online: 17 Jan 2019. * Correspondence: Dr. Gopal Natesan, Faculty of Pharmacy, Mahsa University, Bandar Saujana Putra, Malaysia, gopal@mahsa.edu.my Login Required This action requires you to be registered with Frontiers and logged in. To register or login click here. Abstract Info Abstract The Authors in Frontiers Gopal Natesan Appalaraju Velaga Nelycia Su Yean Tze Soon An Nie Google Gopal Natesan Appalaraju Velaga Nelycia Su Yean Tze Soon An Nie Google Scholar Gopal Natesan Appalaraju Velaga Nelycia Su Yean Tze Soon An Nie PubMed Gopal Natesan Appalaraju Velaga Nelycia Su Yean Tze Soon An Nie Related Article in Frontiers Google Scholar PubMed Abstract Close Back to top Javascript is disabled. Please enable Javascript in your browser settings in order to see all the content on this page.