European Journal of Chemistry 2013, 4(3), 277-284 | doi: https://doi.org/10.5155/eurjchem.4.3.277-284.837 | Get rights and content






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Synthesis and antimicrobial activity of some new 1,2-bis-[1,3-thiazolidin-3-yl]ethane derivatives


Kamal Mohamed Dawood (1,*) , Hussein Khalaf-Allah Abu-Deif (2)

(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).

4_3_277_284

Keywords


Antifungal; Bis-thiourea; Antibacterial; Alfa-Halo ketones; Bis-thiazolidinones; 1,3-Thiazolidin-4-one

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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

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[1]. Kamal M. Dawood
Bis‐thiourea Derivatives and Their Utility in Synthesis of Mono‐heterocyclic, Bis‐heterocyclic, and Fused Heterocyclic Systems
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DOI: 10.1002/jhet.3540
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[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
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[3]. 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
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[4]. 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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How to cite


Dawood, K.; Abu-Deif, H. Eur. J. Chem. 2013, 4(3), 277-284. doi:10.5155/eurjchem.4.3.277-284.837
Dawood, K.; Abu-Deif, H. Synthesis and antimicrobial activity of some new 1,2-bis-[1,3-thiazolidin-3-yl]ethane derivatives. Eur. J. Chem. 2013, 4(3), 277-284. doi:10.5155/eurjchem.4.3.277-284.837
Dawood, K., & Abu-Deif, H. (2013). Synthesis and antimicrobial activity of some new 1,2-bis-[1,3-thiazolidin-3-yl]ethane derivatives. European Journal of Chemistry, 4(3), 277-284. doi:10.5155/eurjchem.4.3.277-284.837
Dawood, Kamal, & Hussein Khalaf-Allah Abu-Deif. "Synthesis and antimicrobial activity of some new 1,2-bis-[1,3-thiazolidin-3-yl]ethane derivatives." European Journal of Chemistry [Online], 4.3 (2013): 277-284. Web. 6 Dec. 2020
Dawood, Kamal, AND Abu-Deif, Hussein. "Synthesis and antimicrobial activity of some new 1,2-bis-[1,3-thiazolidin-3-yl]ethane derivatives" European Journal of Chemistry [Online], Volume 4 Number 3 (30 September 2013)

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DOI Link: https://doi.org/10.5155/eurjchem.4.3.277-284.837

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