Studies on Penam Sulfones. I. Synthesis and .BETA.-Lactamase Inhibitory Activity of 2.BETA.-Alkoxycarbonyl Penicillanic Acid Sulfones.
نویسندگان
چکیده
منابع مشابه
Synthesis and beta-lactamase inhibitory activity of thiazolyl penam sulfones.
In our previous papers1»2), we described the structure-activity relationships of 6-(heterocyclyl)methylene penam sulfones (1) as a new class of /3-lactamase inhibitors and proposed a mechanism of enzyme inactivation for series 1. In continuation of these studies with series 1, we pursued the closely related structures in series 2, since they should follow a similar mechanistic pathway and shoul...
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Production of /Mactamases is by far the most common mechanism of acquired resistance to /Mactam antibiotics. These enzymes efficiently hydrolyze the amide bond of the /Mactam nucleus, yielding products devoid of antibiotic activity. Inhibition of these enzymes has found clinical application, i.e. clavulanic acid which is used in combination with the potent but (otherwise) /Mactamase-sensitive a...
متن کاملPenam Sulfones and β-Lactamase Inhibition: SA2-13 and the Importance of the C2 Side Chain Length and Composition
β-Lactamases are the major reason β-lactam resistance is seen in Gram-negative bacteria. To combat this resistance mechanism, β-lactamase inhibitors are currently being developed. Presently, there are only three that are in clinical use (clavulanate, sulbactam and tazobactam). In order to address this important medical need, we explored a new inhibition strategy that takes advantage of a long-l...
متن کاملCycloaddition reactions of unsaturated sulfones
The reaction of a series of allyl-substituted bis(phenylsulfony1)methanes or dimethyl malonates with 2,3-bis(phenylsulfonyl)l13-butadiene in the presence of base afforded alkenyl-substituted allenes in good yield. The reaction proceeds by initial attack of the soft carbanion onto the terminal position of the diene and subsequent PhS02elimination to give the phenylsulfonyl substituted allene. Th...
متن کاملPreparation of Alkyl Alkynyl Sulfones and Cyclic Vinyl Sulfones from Alkynyl(aryl)iodonium Salts.
The reaction of alkyl sulfinates with alkynyl(aryl)iodonium salts provides a facile access into otherwise difficult to obtain alkyl alkynyl sulfones and cyclic vinyl sulfones via 1,2-rearrangement or 1,5-CH insertion, respectively. In benzyl sulfinates, 1,5-CH insertion is not possible, so addition to the aromatic ring occurs, followed by ring expansion to generate novel bicyclic sulfones.
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ژورنال
عنوان ژورنال: The Journal of Antibiotics
سال: 1996
ISSN: 0021-8820,1881-1469
DOI: 10.7164/antibiotics.49.944