Article ID Journal Published Year Pages File Type
1378905 Bioorganic & Medicinal Chemistry Letters 2005 5 Pages PDF
Abstract

1-(γ-Substituted prolyl)-(S)-2-cyanopyrrolidines were designed based on the predicted binding mode of the known DPP-IV inhibitor NVP-DPP728 and evaluated for their inhibitory activity. In structure–activity relationship study at the γ-position of proline, it became clear that compounds bearing (S)-stereochemistry were 20-fold more potent than the antipode. Of these compounds, the (3,4-dicyanophenyl)amino- and (3-chloro-4-cyanophenyl)amino-derivatives showed the highest inhibitory activity.

Graphical abstract1-((S)-γ-Substituted prolyl)-(S)-2-cyanopyrrolidine was found to be suitable structure for DPP-IV inhibition. Of these, (3,4-dicyanophenyl)amino-(17f) and (3-chloro-4-cyanophenyl)amino-derivatives (17g) showed the highest inhibitory activity.Figure optionsDownload full-size imageDownload as PowerPoint slide

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Physical Sciences and Engineering Chemistry Organic Chemistry
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