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.
| Published in | American Journal of Applied Chemistry (Volume 6, Issue 2) |
| DOI | 10.11648/j.ajac.20180602.15 |
| Page(s) | 64-70 |
| Creative Commons |
This is an Open Access article, distributed under the terms of the Creative Commons Attribution 4.0 International License (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution and reproduction in any medium or format, provided the original work is properly cited. |
| Copyright |
Copyright © The Author(s), 2018. Published by Science Publishing Group |
1,3,4-Thiadiazolines, Spectrometric Confirmation, Antimicrobial Properties
| [1] | 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.http://dx.doi.org/10.1016/S1473-3099(13)70318-9pmid: 24252483 |
| [2] | Antibiotic resistance coalition. Declaration on antibiotic resistance [Internet]. 2014. |
| [3] | Review on antimicrobial resistance. Tackling drug-resistant infections globally [Internet]. London: Wellcome Trust; 2014. Available from: http://amr-review.org [cited 2015 Jan 13]. |
| [4] | 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. |
| [5] | 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 |
| [6] | 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. |
| [7] | 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. |
| [8] | 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. |
| [9] | 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. |
| [10] | 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. |
| [11] | 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. |
| [12] | 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. |
| [13] | 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. |
APA Style
Houssou Raymond Fatondji, Salomé Kpoviessi, Fernand Gbaguidi, Kamirou Chabi Sika, Joachim Gbenou, et al. (2018). Synthesis, Characterization and Antimicrobial Properties of Some 1,3,4-Thiadiazolines. American Journal of Applied Chemistry, 6(2), 64-70. https://doi.org/10.11648/j.ajac.20180602.15
ACS Style
Houssou Raymond Fatondji; Salomé Kpoviessi; Fernand Gbaguidi; Kamirou Chabi Sika; Joachim Gbenou, et al. Synthesis, Characterization and Antimicrobial Properties of Some 1,3,4-Thiadiazolines. Am. J. Appl. Chem. 2018, 6(2), 64-70. doi: 10.11648/j.ajac.20180602.15
AMA Style
Houssou Raymond Fatondji, Salomé Kpoviessi, Fernand Gbaguidi, Kamirou Chabi Sika, Joachim Gbenou, et al. Synthesis, Characterization and Antimicrobial Properties of Some 1,3,4-Thiadiazolines. Am J Appl Chem. 2018;6(2):64-70. doi: 10.11648/j.ajac.20180602.15
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Download@article{10.11648/j.ajac.20180602.15,
author = {Houssou Raymond Fatondji and Salomé Kpoviessi and Fernand Gbaguidi and Kamirou Chabi Sika and Joachim Gbenou and Georges Coffi Accrombessi and Mansourou Moudachirou and Jacques Poupaert},
title = {Synthesis, Characterization and Antimicrobial Properties of Some 1,3,4-Thiadiazolines},
journal = {American Journal of Applied Chemistry},
volume = {6},
number = {2},
pages = {64-70},
doi = {10.11648/j.ajac.20180602.15},
url = {https://doi.org/10.11648/j.ajac.20180602.15},
eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.ajac.20180602.15},
abstract = {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.},
year = {2018}
}
TY - JOUR T1 - Synthesis, Characterization and Antimicrobial Properties of Some 1,3,4-Thiadiazolines AU - Houssou Raymond Fatondji AU - Salomé Kpoviessi AU - Fernand Gbaguidi AU - Kamirou Chabi Sika AU - Joachim Gbenou AU - Georges Coffi Accrombessi AU - Mansourou Moudachirou AU - Jacques Poupaert Y1 - 2018/05/18 PY - 2018 N1 - https://doi.org/10.11648/j.ajac.20180602.15 DO - 10.11648/j.ajac.20180602.15 T2 - American Journal of Applied Chemistry JF - American Journal of Applied Chemistry JO - American Journal of Applied Chemistry SP - 64 EP - 70 PB - Science Publishing Group SN - 2330-8745 UR - https://doi.org/10.11648/j.ajac.20180602.15 AB - 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. VL - 6 IS - 2 ER -
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