The Journal of organic chemistry

Diversity-Oriented Synthesis of a Drug-Like System Displaying the Distinctive N→ C O Interaction

M Waibel, J Hasserodt

Index: Waibel, Michael; Hasserodt, Jens Journal of Organic Chemistry, 2008 , vol. 73, # 16 p. 6119 - 6126

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Citation Number: 12

Abstract

This study describes the syntheses and characterization of two hydrazino ureas. These fold into a six-membered ring by virtue of the infrequently observed δ+ N→ C Oδ− interaction when solvated by polar protic media. The highly polar functional group resulting from this interaction is hypothesized to especially reproduce electronic but also steric features of the transition states of peptide hydrolysis. The urea moiety constitutes an additional key ...