Synthesis, Characterization and Antimicrobial Properties of Some 1,3,4-Thiadiazolines
American Journal of Applied Chemistry
Volume 6, Issue 2, April 2018, Pages: 64-70
Received: Apr. 13, 2018; Accepted: Apr. 26, 2018; Published: May 18, 2018
Views 1695      Downloads 158
Houssou Raymond Fatondji, Faculty of Sciences and Technics (FAST), University of Abomey-Calavi (UAC), Cotonou, Benin
Salomé Kpoviessi, Faculty of Sciences and Technics (FAST), University of Abomey-Calavi (UAC), Cotonou, Benin
Fernand Gbaguidi, Beninese Center for Scientific and Technical Research (CBRST), Oganla, Porto-Novo
Kamirou Chabi Sika, Faculty of Sciences and Technics (FAST), University of Abomey-Calavi (UAC), Abomey, Calavi, Benin
Joachim Gbenou, Beninese Center for Scientific and Technical Research (CBRST), Oganla, Porto-Novo
Georges Coffi Accrombessi, Faculty of Sciences and Technics (FAST), University of Abomey-Calavi (UAC), Cotonou, Benin
Mansourou Moudachirou, Beninese Center for Scientific and Technical Research (CBRST), Oganla, Porto-Novo
Jacques Poupaert, School of Pharmacy, Université Catholique de Louvain (UCL), Brussels, Belgium
Article Tools
Follow on us
Through The literature, there is little information about the antibacterial activity of 1,3,4-thiadiazoles. In order to verify if drugs based on this family of compounds could constitute an alternative to the antibiotics usually used in the antimicrobial fight, the aim of this work was to synthesize, to confirm the structures and then to test some 1,3,4-thiadiazolines for their antimicrobial activity against microbes. Twelve 1,3,4- thiadiazolines were synthesized with yields going from 27 to 95%. The products purity was confirmed by mass spectrometry coupled with high-performance liquid chromatography (LC/MS) and there were characterized using spectrometry IR, NMR 1H and 13C (nuclear magnetic resonance). The synthesized compounds were tested on strains of Escherichia coli ATCC 25922 and Salmonella typhimurium R 30951401 according to the macro-dilution method in liquid environment for a comparison of their antibacterial activity. Thiadiazoline 1 has been shown to be more active than other products. The most antibacterial thiadiazolines are those having para-electro attractor groups and also alkyl groups at R2. It could be a good drug candidate against these microbes.
1,3,4-Thiadiazolines, Spectrometric Confirmation, Antimicrobial Properties
To cite this article
Houssou Raymond Fatondji, Salomé Kpoviessi, Fernand Gbaguidi, Kamirou Chabi Sika, Joachim Gbenou, Georges Coffi Accrombessi, Mansourou Moudachirou, Jacques Poupaert, Synthesis, Characterization and Antimicrobial Properties of Some 1,3,4-Thiadiazolines, American Journal of Applied Chemistry. Vol. 6, No. 2, 2018, pp. 64-70. doi: 10.11648/j.ajac.20180602.15
Copyright © 2018 Authors retain the copyright of this article.
This article is an open access article distributed under the Creative Commons Attribution License ( which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
Laxminarayan R, Duse A, Wattal C, Zaidi AK, Wertheim HF, Sumpradit N, et al. Antibiotic resistance—the need for global solutions. Lancet Infect Dis. 2013 Dec; 13(12):1057–98. 24252483
Antibiotic resistance coalition. Declaration on antibiotic resistance [Internet]. 2014.
Review on antimicrobial resistance. Tackling drug-resistant infections globally [Internet]. London: Wellcome Trust; 2014. Available from: [cited 2015 Jan 13].
Garcia CC, Brousse BN, Carlucci MJ, Moglioni AG, Martins AM, Moltrasio GY, D’Accorso NB, Damonte EB. Inhibitory effect of thiosemicarbazone derivatives on Junin virus replication in vitro. Antivir Chem Chemother 2003; 14:99–105.
Kovač T, Kovač M, Strelec I, Nevistić A, Molnar M (2017) «Antifungal and antiaflatoxigenic activities of coumarinyl thiosemicarbazides against Aspergillus flavus NRRL 3251» DOI: 10.1515/aiht-2017-68-2883
De Araújo Neto LN, do Carmo Alves de Lima M, de Oliveira JF, de Souza ER, Buonafina MDS, Victor Anjos MN, Brayner FA, Alves LC, Neves RP, Mendonça-Jnior FJB (2017) «Synthesis, cytotoxicity and antifungal activity of 5-nitro-thiophene-thiosemicarbazones derivatives» Chem Biol Interact. Jun 25; 272: 172-181. doi: 10.1016/j.cbi.2017.05.005.
Afrasiabi Z, Sinn E, Padhye S, Dutta S, Newton C, Anson CE, Powell AK. Transition metal complexes of phenanthrenequinone thiosemicarbazone as potential anticancer agents: synthesis, structure, spectroscopy, electrochemistry and in vitro anticancer activity against human breast cancer cell-line T47D. J Inorg Biochem 2003; 95(4):306–314.
Afrasiabi Z, Sinn E, Chen JN, Ma YF, Rheingold AL, Zakharov LN, Rath N, Padhye S. Appended 1, 2-naphthoquinones as anticancer agents 1: synthesis, structural, spectral and antitumor activities of ortho-naphthoquinone thiosemicarbazone and its transition metal complexes. Inorg Chim Acta 2004; 357(1):271–278.
Sau DK, Butcher RJ, Chandhuri S, Saha N (2003) Spectroscopic, structural and antibacterial properties of copper (II) complexes with bio-relevant 5-methyl-3-formylpyrazole N (4)-benzyl-N (4) methylthiosemicarbazone. Mol Cell Biochem 2003; 253(1–2):21–22.
Rebolledo AP, de Lima GM, Gambi LN, Speziali NL, Maia DF, Pinheiro CB, Ardisson JD, Cortes ME, Beraldo Hl (2003) Tin (IV) complexes of 2-benzoylpyridine N (4)-phenylthiosemicarbazone: spectral characterization, structural studies and antifungal activity. Appl Organomet Chem 2003; 17: 945.
Labanauskas L, Kalcas V, Udrenaite E, Gaidelis P, Brukstus A, Dauksas V (2001). Synthesis of 3-(3, 4-dimethoxyphenyl)-1 H-1, 2, 4- triazole-5-thiol et 2-amino-5-(3, 4-dimethoxyphenyl)-1, 3, 4-thiadiazole derivatives exhibiting anti-inflammatory activity. Pharmazie., 56: 617.
Chou JY, Lai SY, Pan SL, Chern JW, Guh JH (2003). Investigation ofanticancer mechanism of thiadiazole-based compound in human non-small cell lung cancer A549 cells. Biochem. Pharmacol, 66: 115.
Sancak K, Unver Y, Er M (2007). Synthesis of 2-a, 2-aroylamino et ethoxycarbonyl imino-1,3,4-thiadiazolines as antitumor agents. Turk. J. Chem., 31: 125.
Science Publishing Group
1 Rockefeller Plaza,
10th and 11th Floors,
New York, NY 10020
Tel: (001)347-983-5186