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A Simple Synthesis of 4-Substituted 2-(3-Hydroxy-2-oxo-1-phenethyl- propylcarbamoyl)pyrrolidine-1-carboxylic Acid Benzyl Esters as Novel Cysteine Protease Inhibitors

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A Simple Synthesis of 4-Substituted 2-(3-Hydroxy-2-oxo-1-phenethyl- propylcarbamoyl)pyrrolidine-1-carboxylic Acid Benzyl Esters as Novel Cysteine Protease Inhibitors

Seikwan Oha, Jae-Chul Jungb, and Mitchell A. Averyc

aDepartment of Neuroscience and Medical Research Institute, School of Medicine, Ewha Womans University, Seoul 158-710, South Korea

bEwha Global Challenge, BK21 and Medical Research Institute, School of Medicine, Ewha Womans University, Seoul 158-710, South Korea

cDepartment of Medicinal Chemistry, School of Pharmacy, National Center for Natural Products Research & Department of Chemistry, University of Mississippi, University, MS 38677-1848, USA Reprint requests to Dr. Jae-Chul Jung. Fax: +82-02-2650-5791. E-mail: jcjung@rexgenebio.co.kr or jcjung10@yahoo.co.kr

Z. Naturforsch.2008,63b,210 – 216; received July 18, 2007

A convenient synthesis of 4-substituted 2-(3-hydroxy-2-oxo-1-phenethylpropylcarbamoyl)pyrrol- idine-1-carboxylic acid benzyl esters17and18as new cysteine protease inhibitors is described. The synthetic key strategies involve the diazocarbonyl insertion reaction ofN-Boc-L-homophenylalanine (1) by diazomethane, acetylation of the bromoketone 2with sodium acetate, and condensation of acids12,14with (3S)-3-amino-2-oxo-5-phenyl-pentyl acetate monohydrochloride (4) in good yield.

Key words:Pyrrolidine-1-carboxylic Acid Benzyl Esters, Diazocarbonyl Insertion Reaction, Acetylation, Coupling Reaction, Cysteine Protease Inhibitors

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