Synthesis and biological evaluation of (E)-cinnamic acid, (E)-2-styrylthiazole and (E)-2-[2-(naphthalen-1-yl)vinyl]thiazole derivatives
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Date
Authors
Olawode, Emmanuel O.
Tandlich, Roman
Prinsloo, Earl
Isaacs, Michelle
Hoppe, Heinrich
Seldon, Ronnett
Warner, Digby F.
Steenkamp, Vanessa
Kaye, Perry T.
Journal Title
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Volume Title
Publisher
Michigan Publishing
Abstract
Cinnamyl- and thiazole-based compounds have been shown to exhibit diverse medicinal properties
and a series of twelve (E)-2-styrylthiazole and (E)-2-[(naphthalen-1-yl)vinyl]thiazole derivatives,
which are conjugates of both systems and which satisfy the “Lipinski rule of 5”, have been
synthesised and subjected to in vitro biological screening. While insignificant inhibition (60-98%
viability at 10 μM) of HeLa (cervical cancer) cells was noted, all five of the (E)-2-[naphthalen-1-
yl)vinyl]thiazole derivatives proved remarkably active against SH-SY5Y (neuroblastoma) cells
with IC50 values ranging from 2.09 to 8.64 μM. Two of the seven (E)-2-styrylthiazoles were found
to be moderately active (with IC50 values of 10.8 and 11.7 mM), whereas the remaining five
analogues exhibit significant proliferation of SH-SY5Y cells (with IC50 values of 180-1000 mM).
The results warrant further studies on the effects of styrylthiazoles on the differentiation and
extension of SH-SY5Y cells in order to assess their activity in neurological degenerative diseases.
Description
Keywords
Synthesis, Cinnamic acids, Styrylthiazoles, 2-[2-(Naphthalen-1-yl)vinyl]thiazoles, Biological activity, Peptides, Plasmodium falciparum
Sustainable Development Goals
Citation
Olawode, E.O. et al. 2017, 'Synthesis and biological evaluation of (E)-cinnamic acid, (E)-2-styrylthiazole and (E)-2-[2-(naphthalen-1-yl)vinyl]thiazole derivatives', Arkivoc, Part vi. pp. 284-296.