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Title: Synthesis, antioxidant and antiproliferative activities of 1,3,4-thiadiazoles derived from phenolic acids
Authors: Jakovljević, Katarina
Matic, Ivana
Stanojkovic, Tatjana
Krivokuca, Ana
Marković, Violeta
Joksović, Milan
Mihailović, Nevena
Nićiforović M.
Joksović, Ljubinka
Journal: Bioorganic and Medicinal Chemistry Letters
Issue Date: 1-Jan-2017
Abstract: © 2017 Elsevier Ltd Two 2-amino-1,3,4-thiadiazoles containing phenolic hydroxyl groups were combined with different carboxylic acid chlorides giving sixteen amide derivatives with good antioxidant and antiproliferative potential. The compound 3′c with an adamantane ring displayed excellent DPPH radical scavenging activity and good cytotoxic activity against human acute promyelocytic leukemia HL-60 cells, while 1,3,4-thiadiazole 3′h with 4-chlorophenyl moiety was found to be the most effective in inhibition of survival of lung carcinoma A549 cells. All examined thiadiazoles except 3a and 3′a exerted higher cytotoxic activities on A549 and HL-60 cancer cells when compared with normal fibroblasts MRC-5, pointing to selectivity in their antiproliferative action. Some of the most active novel compounds 3c, 3′c, 3′g and 3′h induced significant increase in the percentage of HL-60 cells in the subG1 cell cycle phase in comparison with the control cells. The induction of cell death in HL-60 cells by these compounds was at least partially dependent on activation of caspase-3 and caspase-8. The compounds 3c and 3′c exerted strong antiangiogenic activity. Furthermore, compounds 3c, 3′c, 3′g and 3′h showed the ability to down-regulate the MMP2 and VEGFA expression levels in the treated HL-60 cells when compared with the control cell samples.
Type: Article
DOI: 10.1016/j.bmcl.2017.07.003
ISSN: 0960894X
SCOPUS: 85021913426
Appears in Collections:Faculty of Science, Kragujevac
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