Regioselective reactions of mesyloxymethylazetidinones with nucleophiles I. Cleavage of the azetidinone ring, azetidinone-aziridine ring transformations

Éva Boros, Ferenc Bertha, Gábor Czira, Antal Feller, J. Fetter, M. Kajtár-Peredy, Gyula Simig

Research output: Contribution to journalArticle

9 Citations (Scopus)

Abstract

The reaction of 4-mesyloxymethylazetidin-2-one derivatives 3 with ammonia and sodium methoxide was investigated, The two electrophilic centers of the substrate reacted successively, resulting in cleavage of the lactam bond and formation of a new aziridine ring, The resulting type 6 and 8 aziridinylacetic acid derivatives are related to the novel 2-(aziridin-2-yl)-3-phenylpropionic acid type carboxypeptidase A inhibitors and, as such, potential drug candidates.

Original languageEnglish
Pages (from-to)87-94
Number of pages8
JournalJournal of Heterocyclic Chemistry
Volume43
Issue number1
DOIs
Publication statusPublished - Jan 2006

Fingerprint

Nucleophiles
Cathepsin A
Carboxypeptidases A
Derivatives
Lactams
Ammonia
Methanol
Acids
Substrates
Pharmaceutical Preparations
2-azetidinone
aziridine
3-phenylpropionic acid

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Regioselective reactions of mesyloxymethylazetidinones with nucleophiles I. Cleavage of the azetidinone ring, azetidinone-aziridine ring transformations. / Boros, Éva; Bertha, Ferenc; Czira, Gábor; Feller, Antal; Fetter, J.; Kajtár-Peredy, M.; Simig, Gyula.

In: Journal of Heterocyclic Chemistry, Vol. 43, No. 1, 01.2006, p. 87-94.

Research output: Contribution to journalArticle

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AU - Simig, Gyula

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