A novel competitive class of alpha-glucosidase inhibitors: (E)-1-phenyl-3-(4-styrylphenyl)urea derivatives = 신규한 알파 글루코시다아제 경쟁적 저해제: (E)-1-Phenyl-3-(4-styrylphenyl)urea 유도체

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Title
A novel competitive class of alpha-glucosidase inhibitors: (E)-1-phenyl-3-(4-styrylphenyl)urea derivatives = 신규한 알파 글루코시다아제 경쟁적 저해제: (E)-1-Phenyl-3-(4-styrylphenyl)urea 유도체
Author(s)
J Y Kim; J W Lee; Y S Kim; Y Lee; Young Bae Ryu; S Kim; Hyung Won Ryu; M J Curtis-Long; K W Lee; Woo Song Lee; K H Park
Bibliographic Citation
Chembiochem, vol. 11, no. 15, pp. 2125-2131
Publication Year
2010
Abstract
Competitive glycosidase inhibitors are generally sugar mimics that are costly and tedious to obtain because they require challenging and elongated chemical synthesis, which must be stereo- and regiocontrolled. Here, we show that readily accessible achiral (E)-1-phenyl-3-(4-strylphenyl)ureas are potent competitive α-glucosidase inhibitors. A systematic synthesis study shows that the 1-phenyl moiety on the urea is critical for ensuring competitive inhibition, and substituents on both terminal phenyl groups contribute to inhibition potency. The most potent inhibitor, compound 12 (IC(50)=8.4 μM, K(i)=3.2 μM), manifested a simple slow-binding inhibition profile for α-glucosidase with the kinetic parameters k(3)=0.005256 μM(-1)?min(-1), k(4)=0.003024 min(-1), and K(i)(app) =0.5753 μM.
Keyword
alpha-glucosidasesdrug designinhibitorsstructureactivity relationshipsurea stilbene
ISSN
1439-4227
Publisher
Wiley
DOI
http://dx.doi.org/10.1002/cbic.201000376
Type
Article
Appears in Collections:
Jeonbuk Branch Institute > Functional Biomaterial Research Center > 1. Journal Articles
Ochang Branch Institute > Natural Medicine Research Center > 1. Journal Articles
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