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 Oh; Jae Chul Jung

doi:10.1515/znb-2008-0215

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 Oh, Jae Chul Jung

Department of Molecular Medicine

Research output: Contribution to journal › Article › peer-review

3 Scopus citations

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.

Original language	English
Pages (from-to)	210-216
Number of pages	7
Journal	Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences
Volume	63
Issue number	2
DOIs	https://doi.org/10.1515/znb-2008-0215
State	Published - Feb 2008

Bibliographical note

Funding Information:
This work has been supported by the KOSEF Brain Neurobiology Grant (2007), by the Ewha Global Challenge (BK21) grant, and in part by Cooperative Agreement Number 1-U01 C1000211 from the Centers for Disease Control and Prevention (M. A. A.).

Keywords

Acetylation
Coupling reaction
Cysteine protease inhibitors
Diazocarbonyl insertion reaction
Pyrrolidine-1-carboxylie acid benzyl esters

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10.1515/znb-2008-0215

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title = "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",

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.",

keywords = "Acetylation, Coupling reaction, Cysteine protease inhibitors, Diazocarbonyl insertion reaction, Pyrrolidine-1-carboxylie acid benzyl esters",

author = "Seikwan Oh and Jung, \{Jae Chul\}",

note = "Funding Information: This work has been supported by the KOSEF Brain Neurobiology Grant (2007), by the Ewha Global Challenge (BK21) grant, and in part by Cooperative Agreement Number 1-U01 C1000211 from the Centers for Disease Control and Prevention (M. A. A.).",

year = "2008",

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doi = "10.1515/znb-2008-0215",

language = "English",

volume = "63",

pages = "210--216",

journal = "Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences",

issn = "0932-0776",

publisher = "Walter de Gruyter GmbH",

number = "2",

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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. / Oh, Seikwan; Jung, Jae Chul.
In: Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences, Vol. 63, No. 2, 02.2008, p. 210-216.

Research output: Contribution to journal › Article › peer-review

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AU - Oh, Seikwan

AU - Jung, Jae Chul

N1 - Funding Information: This work has been supported by the KOSEF Brain Neurobiology Grant (2007), by the Ewha Global Challenge (BK21) grant, and in part by Cooperative Agreement Number 1-U01 C1000211 from the Centers for Disease Control and Prevention (M. A. A.).

PY - 2008/2

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N2 - 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.

AB - 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.

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KW - Coupling reaction

KW - Cysteine protease inhibitors

KW - Diazocarbonyl insertion reaction

KW - Pyrrolidine-1-carboxylie acid benzyl esters

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DO - 10.1515/znb-2008-0215

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JO - Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences

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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

Abstract

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Keywords

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