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

Kamal Mohamed Dawood; Hussein Khalaf-Allah Abu-Deif

doi:10.5155/eurjchem.4.3.277-284.837

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).

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Editor-in-Chief
European Journal of Chemistry

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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Journal of Heterocyclic Chemistry 56(6), 1701, 2019
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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
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[3]. Amer A. Amer, Antar A. Abdelhamid, Amany Sh. Elnakeeb, Hanan A. Salah
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[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
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Expert Opinion on Drug Discovery 17(12), 1357, 2022
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[6]. Javad Safaei-Ghomi, Seyed Hadi Nazemzadeh, Hossein Shahbazi-Alavi
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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. 30 May. 2023

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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