Synthesis and antiproliferative activity of new thiazole hybrids with [3.3.0]furofuranone or tetrahydrofuran scaffolds Scientific paper

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Vesna Kojić
https://orcid.org/0000-0002-2399-0807
Miloš Svirčev
https://orcid.org/0000-0003-1808-1315
Sanja Djokić
https://orcid.org/0000-0003-0448-6282
Ivana Kovačević
https://orcid.org/0000-0001-8218-7590
Marko V. Rodić
https://orcid.org/0000-0002-4471-8001
Bojana Srećo Zelenović
https://orcid.org/0000-0003-0216-2583
Velimir Popsavin
https://orcid.org/0000-0001-9910-2987
Mirjana Popsavin
https://orcid.org/0000-0002-0924-1041

Abstract

New thiazole hybrids were synthesized and evaluated for their in vitro cytotoxicity against a panel of human malignant cell lines. The key steps in the synthesis of hybrids 3–7 involved the initial condensation of appropriate aldononitriles with cysteine ethyl ester hydrochloride, followed by subsequent treatment of resulting thiazolines with DBU to form the thiazole ring. Bioiso­steres 8 and 14 have been prepared after the stereoselective addition of 2-(tri­methylsilyl)thiazole to the hemiacetals obtained by periodate cleavage of terminal diol functionality in the suitably protected d-glucose derivatives. The obtained analogues showed various antiproliferative activities in the cultures of several tumour cell lines. Hybrid 6 was the most potent in HeLa cells, exhibiting more than 10 and 4 times stronger activity than both leads 1 and 2, respectively. The most active compound in Raji cells was hybrid 12, which was nearly 2-fold more potent than the clinical antitumour drug doxorubicin. All analogues were more potent in A549 cells with respect to lead 1, while compounds 6 and 7 were slightly more active than DOX. Preliminary SAR analysis revealed that the presence of a cinnamate group at the C-3 position in analogues of type 7 increases the activity of resulting molecular hybrids.

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How to Cite
[1]
V. Kojić, “Synthesis and antiproliferative activity of new thiazole hybrids with [3.3.0]furofuranone or tetrahydrofuran scaffolds: Scientific paper”, J. Serb. Chem. Soc., Jan. 2023.
Section
Organic Chemistry
Author Biographies

Miloš Svirčev, University of Novi Sad, Faculty of Sciences, Department of Chemistry, Biochemistry and Environmental Protection, Trg Dositeja Obradovića 3, 21000 Novi Sad

    

Bojana Srećo Zelenović, University of Novi Sad, Faculty of Sciences, Department of Chemistry, Biochemistry and Environmental Protection, Trg Dositeja Obradovića 3, 21000 Novi Sad

   

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