

Synthesis and antimicrobial activity of some new 1,2-bis-[1,3-thiazolidin-3-yl]ethane derivatives
Kamal Mohamed Dawood (1,*)


(1) Department of Chemistry, Faculty of Science, Cairo University, Giza 12613, Egypt
(2) Department of Chemistry, Faculty of Science, Cairo University, Giza 12613, Egypt
(*) Corresponding Author
Received: 26 May 2013 | Revised: 12 Jun 2013 | Accepted: 12 Jun 2013 | Published: 30 Sep 2013 | Issue Date: September 2013
Abstract
1,2-Bis-(2-(phenylimino)-4-oxo-1,3-thiazolidin-3-yl)ethane (4) was synthesized and its reaction with various aldehydes afforded the novel 5-arylidene derivatives 5a-e and 7. Reaction of compound 4 with phenyl isothiocyanate in the presence of potassium hydroxide, followed by addition of two equivalents of α-halo ketones furnished the corresponding 1,2-bis-[5-(thiazolidin-2-ylidene)thiazolidin-3-yl]ethane derivatives 10, 14a-c, and 17a,b. The structures of the newly synthesized compounds were established by elemental and spectral analyses. Compounds 5a-e, 7, 10, 14a-c and 17a were screened for their antimicrobial activity against eight microorganisms. All compounds showed high antibacterial and antifungal activities against all the test microorganisms except E. coli and C. albicans. The MIC of the active compounds was also evaluated, where; compounds 10 and 17a were more potent active (minimum inhibitory concentration 0.49 and 0.98 μg/mL, respectively) against S. racemosum than Amphotericin B (MIC 1.95 μg/mL).

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DOI: 10.5155/eurjchem.4.3.277-284.837
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Funding information
Faculty of Science, Cairo University, Giza 12613, Egypt
Citations
[1]. Kamal M. Dawood
Bis‐thiourea Derivatives and Their Utility in Synthesis of Mono‐heterocyclic, Bis‐heterocyclic, and Fused Heterocyclic Systems
Journal of Heterocyclic Chemistry 56(6), 1701, 2019
DOI: 10.1002/jhet.3540

[2]. Tapan Kumar Jena, Faiz Ahmed Khan
Acid mediated synthesis of thiazolines, thiazoles and enamide derivatives from methyl enol ethers: Application towards synthesis of wilsoniamine B
Tetrahedron Letters 61(13), 151675, 2020
DOI: 10.1016/j.tetlet.2020.151675

[3]. Amer A. Amer, Antar A. Abdelhamid, Amany Sh. Elnakeeb, Hanan A. Salah
One‐pot multicomponent designing of novel 2‐imino‐4‐arylidene‐1,3‐thiazolidin‐4‐one
Journal of Heterocyclic Chemistry 60(3), 489, 2023
DOI: 10.1002/jhet.4604

[4]. Kamal M. DAWOOD, Eman A. RAGAB, Korany A. ALI
Synthetic access to some new benzothiazole-based 1,3,4-thiadiazole and 1,3-thiazole derivatives
TURKISH JOURNAL OF CHEMISTRY 40, 277, 2016
DOI: 10.3906/kim-1503-75

[5]. Ashraf A. Abbas, Kamal M. Dawood
Benzofuran as a promising scaffold for the synthesis of novel antimicrobial agents
Expert Opinion on Drug Discovery 17(12), 1357, 2022
DOI: 10.1080/17460441.2023.2157400

[6]. Javad Safaei-Ghomi, Seyed Hadi Nazemzadeh, Hossein Shahbazi-Alavi
Nano-colloidal silica-tethered polyhedral oligomeric silsesquioxanes with eight branches of 3-aminopropyltriethoxysilane as high-performance catalyst for the preparation of bis-thiazolidinones under ultrasonic conditions
Zeitschrift für Naturforschung B 72(12), 927, 2017
DOI: 10.1515/znb-2017-0091

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