A Novel Competitive Class of alpha-Glucosidase Inhibitors: (E)-1-Phenyl-3-(4-Styrylphenyl)Urea Derivatives
- Authors
- Kim, Jun Young; Lee, Ji Won; Kim, Young Soo; Lee, Yuno; Ryu, Young Bae; Kim, Songmi; Ryu, Hyung Won; Curtis-Long, Marcus J.; Lee, Keun Woo; Lee, Woo Song; Park, Ki Hun
- Issue Date
- 18-Oct-2010
- Publisher
- WILEY-V C H VERLAG GMBH
- Keywords
- alpha-glucosidases; drug design; inhibitors; structure-activity relationships; urea stilbene
- Citation
- CHEMBIOCHEM, v.11, no.15, pp.2125 - 2131
- Indexed
- SCIE
SCOPUS
- Journal Title
- CHEMBIOCHEM
- Volume
- 11
- Number
- 15
- Start Page
- 2125
- End Page
- 2131
- URI
- https://scholarworks.bwise.kr/gnu/handle/sw.gnu/24912
- DOI
- 10.1002/cbic.201000376
- ISSN
- 1439-4227
- 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 alpha-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 (IC50 = 8.4 mu m, K-i = 3.2 mu m), manifested a simple slow-binding inhibition profile for alpha-glucosidase with the kinetic parameters k(3) = 0.005256 mu m(-1) min(-1), k(4) = 0.003024 min(-1), and K-i(app) = 0.5753 mu m.
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