Ishak, Syarmila
(2019)
Synthesis, Characterization And
Biological Studies On Symmetrical 2,7-
Disubstituted 9,9’-Dihexylfluorene
Derivatives With Amine And Ether
Bridging Groups.
Masters thesis, Universiti Sains Malaysia.
Abstract
Three new fluorene derivatives namely, 1,1’-(9,9-dihexyl-9H-fluorene-2,7-
diyl)bis(N,N-bis(pyridine-2-ylmethyl)methanamine (FP1), 1,1'-(9,9-dihexyl-9Hfluorene-
2,7-diyl)bis(N,N-bis(benzo[d]thiazol-2-ylmethyl)methanamine (FT2) and
8,8'-(((9,9-dihexyl-9H-fluorene-2,7-diyl)bis(methylene))bis(oxy))diquinoline (FQ3)
have been successfully synthesized in moderate yield 60 %, 66 % and 63 %,
respectively. The molecular structure of all the synthesized compounds were
elucidated via FT-IR, 1H NMR, 13C NMR, DEPT, 1H-1H COSY, 1H-13C HMQC, 1H-
13C HMBC spectroscopy. Fluorescence properties of all the final compounds were
examined by UV-Vis and fluorescence. Biological studies including in-vitro
cytotoxicity, antimicrobial and antioxidant activities of the title compounds were
investigated. The in-vitro cytotoxic activity of the title compounds was evaluated
against human cervical (HeLa) cancer cell line, with 5-fluororacil used as standard
drug (IC50 = 27.82 μg/mL). FP1 demonstrated cytotoxic activity with IC50 value
28.58 ± 0.05 μg/mL while FT2 and FQ3 showed no activity for HeLa cell as the IC50
values were determined to be 141.13 ± 0.03 μg/mL and 223.81 ± 0.02 μg/mL,
respectively. Antioxidant activity of the target compounds was demonstrated by
DPPH radical scavenging activity where the title compounds were found to exhibit
very low scavenging activity.
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