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- Title
Synthesis and antiproliferative activity of new thiazole hybrids with [3.3.0]furofuranone or tetrahydrofuran scaffolds.
- Authors
KOJIĆ, VESNA; SVIRČEV, MILOŠ; DJOKIĆ, SANJA; KOVAČEVIĆ, IVANA; RODIĆ, MARKO V.; SREĆO ZELENOVIĆ, BOJANA; POPSAVIN, VELIMIR; POPSAVIN, MIRJANA
- 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 aldo-nonitriles with cysteine ethyl ester hydrochloride, followed by subsequent treatment of resulting thiazolines with diazabicycloundecene to form the thiaz-ole 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 doxo-rubicin. All analogues were more potent in A549 cells with respect to lead 1, while compounds 6 and 7 were slightly more active than doxorubicin. Preliminary structure-activity relationship 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.
- Subjects
TETRAHYDROFURAN; HELA cells; STRUCTURE-activity relationships; ETHYL esters; CANCER cells; HEMIACETALS; THIAZOLES
- Publication
Journal of the Serbian Chemical Society, 2023, Vol 88, Issue 5, p487
- ISSN
0352-5139
- Publication type
Article
- DOI
10.2298/JSC221130002K