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Arylsulfonyl histamine derivatives as powerful and selective α-glucosidase inhibitors
A series of simple N -arylbenzenesulfonyl histamine derivatives were prepared and screened against α-glucosidase. Inhibition was in the micromolar range for several N α , N τ -di-arylsulfonyl compounds, with N α , N τ -di-4-trifluorobenzenesulfonyl histamine ( IId ) being the best inhibitor. Compoun...
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Published in: | MedChemComm 2020-04, Vol.11 (4), p.518-527 |
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Main Authors: | , , , , , , |
Format: | Article |
Language: | English |
Subjects: | |
Citations: | Items that this one cites Items that cite this one |
Online Access: | Get full text |
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Summary: | A series of simple
N
-arylbenzenesulfonyl histamine derivatives were prepared and screened against α-glucosidase. Inhibition was in the micromolar range for several
N
α
,
N
τ
-di-arylsulfonyl compounds, with
N
α
,
N
τ
-di-4-trifluorobenzenesulfonyl histamine (
IId
) being the best inhibitor. Compound
IId
is a reversible and competitive α-glucosidase inhibitor, and presented good selectivity with respect to other target enzymes, including β-glucosidase and α-amylase, and interesting predicted physicochemical properties. Docking studies have been run to postulate ligand-enzyme interactions to account for the experimental results.
In vivo
, compound
IId
produced a similar hypoglycemic effect to acarbose with half of its dose.
N
α
,
N
τ
-Di-4-trifluorobenzenesulfonyl histamine inhibits α-glucosidase
in vitro
reversibly and selectively with a
K
i
value of 11.6 μM, and shows an
in vivo
hypoglycemic effect in mice. |
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ISSN: | 2632-8682 2040-2503 2632-8682 2040-2511 |
DOI: | 10.1039/c9md00559e |