Synthesis and Antibacterial Activity of 3-Acylamino-3-methoxy-2-azetidinone-1-sulfonic Acid Derivatives

As a key intermediate for the synthesis of sulfazecin derivatives, 3-amino-3-methoxy-2-azetidinone (24 or 26) was synthesized from penicillins, and various new compounds, including sulfazecin, were synthesized by acylation and sulfonation of 24 or 26. Some of these compounds (33, 36) showed higher a...

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Veröffentlicht in:	Chemical & pharmaceutical bulletin 1983/07/25, Vol.31(7), pp.2200-2208
Hauptverfasser:	MATSUO, TAISUKE, MASUYA, HIROTOMO, SUGAWARA, TOHRU, KAWANO, YASUHIKO, NOGUCHI, NORIYOSHI, OCHIAI, MICHIHIKO
Format:	Artikel
Sprache:	eng
Schlagworte:	Anti-Bacterial Agents - chemical synthesis antibacterial activity Azetidines - chemical synthesis Azetidines - pharmacology Azetines - chemical synthesis Chemical Phenomena Chemistry Escherichia coli Escherichia coli - drug effects Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with only one n hetero atom and condensed derivatives Organic chemistry Preparations and properties Sulfonic Acids - chemical synthesis Sulfonic Acids - pharmacology
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Beschreibung
Zusammenfassung:	As a key intermediate for the synthesis of sulfazecin derivatives, 3-amino-3-methoxy-2-azetidinone (24 or 26) was synthesized from penicillins, and various new compounds, including sulfazecin, were synthesized by acylation and sulfonation of 24 or 26. Some of these compounds (33, 36) showed higher antibacterial activity than the corresponding 3-demethoxy derivatives against a β-lactamase-producing strain of Escherichia coli.
ISSN:	0009-2363 1347-5223
DOI:	10.1248/cpb.31.2200