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Synthetic studies and biological evaluation of chromone - 3 - carbaldehydes

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dc.contributor.advisor Ramaite, I D. I.
dc.contributor.advisor Muyakeni - Moleele, S. S.
dc.contributor.author Gordon, Allen Tauya
dc.date.accessioned 2018-10-05T08:50:58Z
dc.date.available 2018-10-05T08:50:58Z
dc.date.issued 2018-08-21
dc.identifier.uri http://hdl.handle.net/11602/1214
dc.description MSc (Chemistry)
dc.description Department of Chemistry
dc.description.abstract Chromones are well known naturally occurring heterocyclic compounds with oxygen as a heteroatom. Chromones are also one of the major classes of naturally occurring compounds, and the interest in their chemistry is due to their wide range of their biological activity. In this study, three classes of target compounds were synthesized through three different pathways. The first pathway, chromone-3-carbaldehyde analogues were afforded in good to excellent yield followed by the oxidation thereof to 4-oxo-4H-chromene-3-carboxylic acids. A series of chromone-3-carboxamides was obtained from corresponding 4-oxo-4H-chromene-3-carboxylic acid via the in situ generation of the corresponding acid chloride in good yield. The second class of compounds were achieved by reacting corresponding chromone-3-carbaldehyde analogues with thiazolidine-2,4-dione to afford 5-((4-oxo-4H-chromen-3-yl)methylene)thiazolidine-2,4-dione analogues. The third class of compounds followed the same reaction pathway as the second class of compounds from corresponding 8-allyl-chromone-3-carbaldehyde analogues to afford 5-((8-allyl-4-oxo-4H-chromen-3-yl)methylene)thiazolidine-2,4-dione analogues in good yield. Compounds were characterized by 1D NMR (1H, 13C and DEPT), 2D NMR (COSY, HSQC and HMBC), IR and elemental analysis (CHN analysis). Selected synthesized chromone derivatives were evaluated in vitro for two biological assays; namely trypanocidal activity and cytotoxicity. Among all tested compounds, 41A, 55B and 63D displayed promising trypanocidal activity by reducing the percentage parasite viability to 0.61, 0.15 and 0.21 respectively. These results were further substantiated by their IC50 values 4.3, 1.3 and 1.9 μg/mL respectively. Compounds 41B and 59A also showed significant trypanocidal activity, however it was below the positive control. Compounds 41A and 55B displayed cytotoxicity against the HeLa cells whilst compound 63D displayed no toxicity against the HeLa cells. en_US
dc.description.sponsorship NRF en_US
dc.format.extent 1 online resource (xiv, 128 pages : illustrations (some color)
dc.language.iso en en_US
dc.rights University of Venda
dc.subject Chromosomes en_US
dc.subject Heterocyclic en_US
dc.subject In vitro en_US
dc.subject Trypanocidal activity en_US
dc.subject Cytotoxity en_US
dc.subject Chomone - 3 - Carbaldehydes en_US
dc.title Synthetic studies and biological evaluation of chromone - 3 - carbaldehydes en_US
dc.type Dissertation en_US

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