Synthesis, Characterization And Biological Evaluation Of Naphthalene- And Coumarin-Based Chalcones

dc.contributor.authorLim, Sumithda Yeong Hui
dc.date.accessioned2017-01-04T03:31:40Z
dc.date.available2017-01-04T03:31:40Z
dc.date.issued2016-03
dc.description.abstractThis study was started by the synthesis and characterization of two main series of starting materials: alkylation of naphthaldehydes (2-8) and acetylation of substituted coumarins (9-11). The starting materials thus obtained were elucidated by the spectroscopic methods such as fourier transform infrared (FTIR), nuclear magnetic resonance (NMR) and CHN microanalyses. Single crystal X-ray diffraction (XRD) analyses have also been carried out wherein the crystals of compound 3, 34 and 41 crystallized in a triclinic crystal system. Five novel series of chalcones were subsequently synthesized by means of Claisen-Schmidt condensation wherein three series were derived from substituted acetyl coumarins (12-33) and the remaining two series was derived from substituted acetophenones (34-46). All the synthesized chalcones were characterized by elemental analysis (CHN), FTIR, 1H-NMR, 13C-NMR, DEPT 135, 1H-1H COSY, 1H-13C HMQC and 1H-13C HMBC spectroscopy. Selected chalcones, 23, 28, 34, and 41 were selected for crystallography analysis. The synthesized chalcones were evaluated for their pharmacological (anti-cancer) properties against breast cancer cell (4T1) and fibroblast cell (NIH-3T3) with cisplatin as positive control. Based on the data obtained, chalcones comprised of coumarin rings showed more potent cytotoxicity against breast cancer cell compared to chalcones comprised of common phenyl rings. Compound 17 exhibited the highest inhibitory activity against 4T1 cancer cell line among the synthesized chalcones and five times (IC50 = 3±0.00) more active compared to cisplatin (IC50 = 16.5±0.71). Chalcones 13, 14, 15, 16, 24 and 31 also showed high inhibitory activities against 4T1 cancer cell line with IC50 < 20.5 μM. The results also indicated that fluorinated chalcones (IC50 value ranged from 28-62 μM) may serve as better anti-breast cancer agents than the chalcones without fluorine (IC50 > 92.5 μM).en_US
dc.identifier.urihttp://hdl.handle.net/123456789/3306
dc.language.isoenen_US
dc.publisherUniversiti Sains Malaysiaen_US
dc.subjectSynthesisen_US
dc.subjectCharacterizationen_US
dc.titleSynthesis, Characterization And Biological Evaluation Of Naphthalene- And Coumarin-Based Chalconesen_US
dc.typeThesisen_US
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