A Simple Synthesis of 4-Substituted 2-(3-Hydroxy-2-oxo-1-phenethylpropylcarbamoyl) pyrrolidine-1-carboxylic Acid Benzyl Esters as Novel Cysteine Protease Inhibitors-Reference-Cited by-同舟云学术

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

Published:2008-02-01 Issue:2 Volume:63 Page:210-216
ISSN:1865-7117
Container-title:Zeitschrift für Naturforschung B
language:en
Short-container-title:

Author:

Oh Seikwan¹,Jung Jae-Chul²,Avery Mitchell A.³

Affiliation:

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

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

3. Department of Medicinal Chemistry, School of Pharmacy, National Center for Natural Products Research & Department of Chemistry, University of Mississippi, University, MS 38677-1848, USA

Abstract

A convenient synthesis of 4-substituted 2-(3-hydroxy-2-oxo-1-phenethylpropylcarbamoyl)pyrrolidine- 1-carboxylic acid benzyl esters 17 and 18 as new cysteine protease inhibitors is described. The synthetic key strategies involve the diazocarbonyl insertion reaction of N-Boc-L-homophenylalanine (1) by diazomethane, acetylation of the bromoketone 2 with sodium acetate, and condensation of acids 12, 14 with (3S)-3-amino-2-oxo-5-phenyl-pentyl acetate monohydrochloride (4) in good yield

Publisher

Walter de Gruyter GmbH

Subject

General Chemistry

Link

https://www.degruyter.com/document/doi/10.1515/znb-2008-0215/pdf

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