Synthesis, anticorrosion, antibacterial, and antifungal activity of new amphiphilic compounds possessing quinazolin-4(3
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Synthesis, anticorrosion, antibacterial, and antifungal activity of new amphiphilic compounds possessing quinazolin-4(3H)-one scaffold S. Öztürk,a S. Okay,b,c and A. Yıldırıma aDepartment
of Chemistry, Bursa Uludağ University, Bursa 16059, Turkey. E-mail: [email protected] bDepartment of Biology, Çankırı Karatekin University, Çankırı 18100, Turkey cVaccine Institute, Hacettepe University, Ankara 06230, Turkey For the first time, quinazolin-4(3H)-one-based cationic surfactants were prepared and fully characterized by IR and NMR spectroscopic techniques and elemental analysis. Some of their physicochemical properties, such as density, critical micelle concentration, surface tension, effectiveness in surface tension reduction, Gibbs free energy of micellization, foam and emulsion stability, and anticorrosion activity were determined. Antibacterial and antifungal activities of the synthesized compounds were investigated. N,N-Dimethyl-N-{2-[(2-methyl-4-oxoquinazolin-3(4H)-yl)amino]-2-oxoethyl}tetradecan-1-aminium chloride (4a) showed the highest antibacterial activity against five human pathogens. Antifungal activity against Candida albicans was shown only by surfactant 4a. Key words: anticorrosion activity, antibacterial activity, antifungal activity, heterocyclic surfactants, quinazolin-4(3H)-one, Gibbs free energy of micellization.
Nitrogen-containing heterocyclic compounds are an important class of organic compounds due to their diverse biological activities. The representatives of this class of heterocycles are the derivatives of quinazolin-4(3H)-one (also known as 4-oxo-quinazoline).1 The name quinazoline, earlier known as benzo-1,3-diazine, was first proposed for this bicyclic compound by Weddige.2 The facile synthesis of quinazolin-4(3H)-one by heating the starting material anthranilic acid with excess formamide in an open vessel at 120 C is known as Niementowski reaction3 (Scheme 1). Another procedure employed by Jiang and co-workers4 involved the treatment of 5-chloroanthranilic acid with acetic anhydride to afford the benzoxazinone in 76% yield. Subsequent stirring of benzoxazinone with ammonium acetate at an elevated temperature afforded 6-chloro-2-methylquinazolin-4(3H)-one in 54% yield (Scheme 2). Similar reaction was also performed in good yields by Nouira et al.5 under microwave irradiation conditions (200 W) over 10 min at 200 C. These findings clearly indicate that significant advancement has been made in recent years in the synthesis of these heterocyclic compounds. Heterocyclic compounds with quinazolin-4(3H)-one skeleton garnered great interest because of their biological activities, such as anticancer,6—8 antimicrobial,9—11 antifungal,12 anti-inflammatory,11,13—15 analgesic,13—16
Scheme 1
Scheme 2
i. Ac2O, reflux; ii. NH4OAc, 150 C, 0.5 h.
anticonvulsant,16,17 antitumor,18,19 antiviral,20,21 and antibacterial13,14,22,23 properties.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2205—2214, November, 2020. 1066-5285/20/6911-2205 © 2020 Springer Scie
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