Aouali et al., Med chem (Los Angeles) 2016, 6:4 DOI: 10.4172/2161-0444.1000356 Research Article M e d i c i n a l c h e m i s t r y ISSN: 2161-0444 Medicinal chemistry Open Access Med chem (Los Angeles) ISSN: 2161-0444 Med chem (Los Angeles), an open access journal Volume 6(4): 264-269 (2016) - 264 *Corresponding author: Monia Aouali, Laboratoire de Chimie Appliquée: Hétérocycles, Corps Gras et Polymères, Faculté des Sciences, University of Sfax, 3018 Sfax, Tunisie, Tel: +21626299719; E-mail: aoualimonia@yahoo.fr Received April 11, 2016; Accepted April 21, 2016; Published April 26, 2016 Citation: Aouali M, Masmoudi F, Allouche F, Kaim LE, Chabchoub F, et al. (2016) Design, Microwave-Assisted Synthesis and Biological Activities of 1,2,4-Triazol-3- Yl-Thiazolidin-4-Ones. Med chem (Los Angeles) 6: 264-269. doi:10.4172/2161- 0444.1000356 Copyright: © 2016 Aouali M, et al. This is an open-access article distributed under the terms of the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original author and source are credited. Design, Microwave-Assisted Synthesis and Biological Activities of 1,2,4-Triazol-3-Yl-Thiazolidin-4-Ones Monia Aouali 1* , Fatma Masmoudi 3 , Fatma Allouche 1 , Laurent El Kaim 2 , Fakher Chabchoub 1 and Mohamed Trigui 3 1 Laboratoire de Chimie Appliquée: Hétérocycles, Corps Gras et Polymères, Faculté des Sciences, University of Sfax, Tunisie 2 Laboratoire Chimie et Procédés, DCSO, UMR 7652, Ecole Nationale Supérieure de Techniques Avancées, 828 Bd des Maréchaux, France 3 Laboratoire des Biopesticides, Centre de biotechnologie de Sfax Université de Sfax, Tunisie Keywords: Aminotriazoles; Triazolothiazolidinones; Antimicrobial activity; Antioxidant activity Introduction Bacterial infections are a common problem in hospitals and clinical setting worldwide and have become an increasing public health problem. Te indiscriminate and the overuse of antibiotics has led to the emergence of antibiotic-resistant bacteria such us Methicillin- resistant Staphylococcus aureus [1]. Tus, designing and developing new antimicrobial agents having new modes of action are being a big challenge for scientifc. Triazolothiazolidinones have received intensive research interests due to their biological activities, and found a wide range of applications in pharmaceutical and agrochemical feld. Tiazolidin-4-one is a versatile scafold for designing potential bioactive agents. In fact, some derivatives of thiazolidin-4-one showed an antioxidant, anticancer [2], antitumor [3], anti-infammatory [4], antimicrobial [5], anti-HIV [6], antiviral [7], anticonvulsant [8] and antihypertensive [9] activities. Moreover, Reactive Oxygen Species (ROS) are various forms of activated oxygen. A disproportion of the reactive oxygen species and the absence of their scavenge systems in cells leads to oxidative stress and increases the risk of several human chronic diseases [10]. In previous papers [11,12] we reported that derivatives of aminotriazoles can be used such as starting materiel for obtaining polyheterocyclic compounds having interest biological activities. In continuation, we present here our study of three-component reaction of aminotriazoles, aromatic aldehydes and mercaptoacetic acid and valorization of biological activities of some triazolothiazolidinones obtained. Materials and Methods Chemistry All microwave-assisted reactions were carried out in synthetic microwave: Monowave 300 with a maximum power of 300 W. Te reactions were followed by TLC (aluminium sheets with silica gel 60 F254 from Merck). 1 H NMR and 13 C NMR spectra were recorded at 400 MHz using CDCl 3 -d 6 on a Bruker Spectrometer and High Resolution Mass Spectra HRMS. Chemical shifs (δ) are expressed in parts per million (ppm) relative to tetramethylsilane (TMS) as internal reference. Te multiplicities abbreviations were used: s, singlet; d, doublet; dd doublet of doublet; t, triplet; q, quadruplet; m, multiplet. Coupling constants J are expressed in Hertz. Melting points were measured on an Electrothermal apparatus. General procedure for the synthesis of 3-(5-alkyl-2-phenyl-2H- 1,2,4-triazol-3-yl)thiazolidin-4-ones 2a-p: 5-amino-1-phenyl-1,2,4- triazoles (1 mmol) and aromatics aldehydes (1 mmol) were added to a 10% Sm(SO 3 CF 3 ) 3 in 1 mL dry toluene, Te mixture were stirred at 180°C in sealed tube by irradiating microwave for 15 min. Subsequently, thioglycolic acid (1.3 mmol) was added and was irradiated in a microwave at 140°C for 15 min. Afer, N,N′-dicyclohexylcarbodiimide DCC (1.3 mmol) and additional dry toluene were added. Te mixture was stirred at 140°C in sealed tube by irradiating microwave for 15 min reaction. Ten, afer cooled to room temperature, 1,3-dicyclohexylurea (DCU) was removed by fltration and the residue was purifed by chromatography on silica gel (petroleum ether/CH 2 Cl 2 (6:4)). Biological activities Microorganisms and growth conditions: Te synthesized compounds were tested against a panel of microorganisms including eight bacteria and six fungal strains obtained from American Type Culture Collection (ATCC), local culture Collection of Tunisian Microorganisms “CTM” of the Centre of Biotechnology of Sfax, Collection of the Institut Pasteur (CIP) and Plant Pathology Experimental Institute (ISPAVE). Te tested pathogenic bacteria are: Bacillus cereus ATCC 14579, Staphylococcus aureus ATCC 25923, Enterococcus faecalis ATCC 29212, Micrococcus luteus ATCC 1880, Esherichia coli ATCC 25922, Klebsiella pneumoniae ATCC 10031, Salmonella enteritidis (food isolate 824), Listeria monocytogenes (food isolate 2132). Te fungi tested are Rhizopus nigricans (LPAP26); Alternaria alternata CTM 10230; Pythium phanidermatum (LPAP32); Fusarium culmorum ISPAVE 21W; Fusarium graminearum ISPAVE 271; Aspergillus favus (food isolate). Bacteria were cultivated in Muller-Hinton agar (MH) Abstract A new 3-(5-alkyl-2-phenyl-2H-1,2,4-triazol-3-yl)thiazolidin-4-ones derivatives were obtained by condensation of 5-amino-1,2,4-triazoles, mercaptoacetic acid with aromatic aldehydes and catalyzed by Sm(SO 3 CF 3 ) 3 using microwave irradiation. The prepared compounds were tested for their antioxidant, antibacterial and antifungal proprieties. Some of these compounds displayed signifcant activities. Among them, compound 2e exhibited remarkable activity against a broad spectrum of Gram positive, negative bacteria and pathogenic fungal strains with low MIC values. The investigation of the mode of action of the most potent antifungal compounds on the fungus Pythium phanidermatum showed a membrane alteration and distortions of hyphal morphology. The newly synthesized compounds exhibited also promising radical scavenging activity.