Chalcones and bis-chalcones: As potential α-amylase inhibitors; synthesis, in vitro screening, and molecular modelling studies
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Date
2018-05-07
Authors
Bale, A.T.
Khan, K.M.
Salar, U.
Chigurupati, S.
Fasina, T.M.
Ali, F.
Kanwal
Wadood, A.
Taha, M.
Nanda, S.S.
Journal Title
Journal ISSN
Volume Title
Publisher
Elsevier
Abstract
Despite of a diverse range of biological activities associated with chalcones and bis-chalcones, they are still neglected by the medicinal chemist for their possible α-amylase inhibitory activity. So, the current study is based on the evaluation of this class for the identification of new leads as α-amylase inhibitors. For that purpose, a library of substituted chalcones 1–13 and bis-chalcones 14–18 were synthesized and characterized by spectroscopic techniques EI-MS and 1H NMR. CHN analysis was carried out and found in agreement with the calculated values. All compounds were evaluated for in vitro α-amylase inhibitory activity and demonstrated good activities in the range of IC50 = 1.25 ± 1.05–2.40 ± 0.09 µM as compared to the standard acarbose (IC50 = 1.04 ± 0.3 µM). Limited structure–activity relationship (SAR) was established by considering the effect of different groups attached to aryl rings on varying inhibitory activity. SMe group in chalcones and OMe group in bis-chalcones were found more influential on the activity than other groups. However, in order to predict the involvement of different groups in the binding interactions with the active site of α-amylase enzyme, in silico studies were also conducted.
Description
Staff publications
Keywords
Research Subject Categories::NATURAL SCIENCES::Chemistry::Organic chemistry::Bioorganic chemistry , Chalcones , Bis-chalcones , In vitro , α-amylase , inhibitory activity , Structure-activity relationship
Citation
Bale, A. T., [Et...al] (2018). Chalcones and bis-chalcones: As potential α-amylase inhibitors; synthesis, in vitro screening, and molecular modelling studies. Bioorganic chemistry, Vol.79, 179-189pp.