European Journal of Chemistry 2015, 6(2), 157-162 | doi: https://doi.org/10.5155/eurjchem.6.2.157-162.1219 | Get rights and content

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Design, synthesis, antimicrobial activity and anticancer screening of some new 1,3-thiazolidin-4-ones derivatives


Wesam Saber Shehab (1,*) , Samar Mohamed Mouneir (2)

(1) Department of Chemistry, Faculty of Science, Zagazig University, Zagazig, 44511, Egypt
(2) Department of Pharmacology, Faculty of Veterinary Medicine, Cairo University, Cairo, 12211, Egypt
(*) Corresponding Author

Received: 17 Nov 2014 | Accepted: 01 Feb 2015 | Published: 30 Jun 2015 | Issue Date: June 2015

Abstract


A series of new thiazolidin-4-ones have been synthesized by the reaction of 3-acetylindole with thiourea to yield 2-amino-arylthiazole (1) which, reacted with 2-chloroacetyl chloride to produce 2-chloroacetamido-4-arylthiazoles (2). The later was treated with potassium thiocyanate to afford the related 2-amino-3-(4-arylthiazol-2-yl) thiazolidin-4-ones (3). Condensation of compounds 1 and 3 with different aromatic aldehydes give Schiff’s bases (4a-c) and (5a-c) reaction of compound 5a-c with thioglycollic acids furnishes the target thiazolidin-4-one molecules (6a-c). Further, condensation of compound 6a with benzaldehyde affords benzylidenethiazolo derivative (7) which on refluxing with malononitrile, acetylacetone afforded thiazolopyridine derivatives (8,9). Structure elucidation of the products has been accomplished on the basis of elemental analysis, IR, 1H NMR data. Compound 3exhibited the most potent antibacterial and anticancer activity.


Keywords


Anticancer; Schiff’s bases; 3-Acetylindol; Antimicrobial; 1,3-Thiazolidin-4-ones; Thiazolopyridine derivatives

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DOI: 10.5155/eurjchem.6.2.157-162.1219

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Citations

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[1]. Wesam Shehab, Maged Aziz, Nourhan Elhoseni, Mohamed Assy, Magda Abdellattif, Eman Hamed
Design, Synthesis, Molecular Docking, and Evaluation Antioxidant and Antimicrobial Activities for Novel 3-Phenylimidazolidin-4-One and 2-Aminothiazol-4-One Derivatives
Molecules  27(3), 767, 2022
DOI: 10.3390/molecules27030767
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[2]. Reda A. Haggam, Mohamed G. Assy, Enaiat K. Mohamed, Abdussattar S. Mohamed
Synthesis of Pyrano[2,3‐ d ]pyrimidine‐2,4‐diones and Pyridino[2,3‐ d ]pyrimidine‐2,4,6,8‐tetraones: Evaluation Antitumor Activity
Journal of Heterocyclic Chemistry  57(2), 842, 2020
DOI: 10.1002/jhet.3830
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[3]. Wesam S. Shehab, Gehan T. El-Bassyouni
Synthesis and cyclization of β-keto-enol derivatives tethered indole and pyrazole as potential antimicrobial and anticancer activity
Journal of the Iranian Chemical Society  15(7), 1639, 2018
DOI: 10.1007/s13738-018-1362-7
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[4]. Javeed Ahmad War, Santosh Kumar Srivastava, Savitri Devi Srivastava
Design, synthesis and molecular docking studies of some morpholine linked thiazolidinone hybrid molecules
European Journal of Chemistry  7(3), 271, 2016
DOI: 10.5155/eurjchem.7.3.271-279.1427
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[5]. Wesam S. Shehab, Magda H. Abdellattif, Samar M. Mouneir
Heterocyclization of polarized system: synthesis, antioxidant and anti-inflammatory 4-(pyridin-3-yl)-6-(thiophen-2-yl) pyrimidine-2-thiol derivatives
Chemistry Central Journal  12(1), , 2018
DOI: 10.1186/s13065-018-0437-y
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[6]. Magda H. Abdellattif, Mohamed Mohamed Helmy Arief, Adel A. H. Abdel-Rahman, Abdel-Aleem H. Abdel Aleem, Abdel Moneam Farag Eissa
Green Synthesis of Novel 5-Arylazo-2-[(2S, 3S, 4R, 5R)-3, 4, 5-Trihydroxy-6-(Hydroxymethyl) Tetrahydro-2H-Pyran-2-Yloxy]-4, 6-Dimethyl 3-Nicotinonitrile
International Journal of Organic Chemistry  07(04), 389, 2017
DOI: 10.4236/ijoc.2017.74031
/


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How to cite


Shehab, W.; Mouneir, S. Eur. J. Chem. 2015, 6(2), 157-162. doi:10.5155/eurjchem.6.2.157-162.1219
Shehab, W.; Mouneir, S. Design, synthesis, antimicrobial activity and anticancer screening of some new 1,3-thiazolidin-4-ones derivatives. Eur. J. Chem. 2015, 6(2), 157-162. doi:10.5155/eurjchem.6.2.157-162.1219
Shehab, W., & Mouneir, S. (2015). Design, synthesis, antimicrobial activity and anticancer screening of some new 1,3-thiazolidin-4-ones derivatives. European Journal of Chemistry, 6(2), 157-162. doi:10.5155/eurjchem.6.2.157-162.1219
Shehab, Wesam, & Samar Mohamed Mouneir. "Design, synthesis, antimicrobial activity and anticancer screening of some new 1,3-thiazolidin-4-ones derivatives." European Journal of Chemistry [Online], 6.2 (2015): 157-162. Web. 4 Oct. 2022
Shehab, Wesam, AND Mouneir, Samar. "Design, synthesis, antimicrobial activity and anticancer screening of some new 1,3-thiazolidin-4-ones derivatives" European Journal of Chemistry [Online], Volume 6 Number 2 (30 June 2015)

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