1994
DOI: 10.1021/jm00050a016
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7-Azetidinylquinolones as Antibacterial Agents. 2. Synthesis and Biological Activity of 7-(2,3-Disubstituted-1-azetidinyl)-4-oxoquinoline- and -1,8-naphthyridine-3-carboxylic Acids. Properties and Structure-Activity Relationships of Quinolones with an Azetidine Moiety

Abstract: A series of 7-(2,3-disubstituted-1-azetidinyl)-1,4-dihydro-6-fluoro-4- oxoquinoline- and -1,8-naphthyridine-3-carboxylic acids, with varied substituents at the 1-, 5-, and 8-positions, was prepared to study the effects on potency and physicochemical properties of the substituent at position 2 of the azetidine moiety. The activity of the title compounds was determined in vitro against Gram-positive and Gram-negative bacteria, and the in vivo efficacy of selected derivatives was determined using a mouse infectio… Show more

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Cited by 47 publications
(21 citation statements)
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“…Since the desirable reaction did not proceed under the same conditions as described in Table 3, we focused on N-benzyl-3-bromoazetidine (13) 8) which can be exploited to synthesize various azetidine derivatives via suitable nucleophilic substitution reaction. The compound 13 was obtained via two steps of reactions involving the ringopening reaction of ABB (3) with HBr to give 3-bromoazetidine hydrobromide (12) followed by benzyl protection of the N1 group, but this reaction procedure resulted in a low yield (24% total yield).…”
Section: Resultsmentioning
confidence: 99%
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“…Since the desirable reaction did not proceed under the same conditions as described in Table 3, we focused on N-benzyl-3-bromoazetidine (13) 8) which can be exploited to synthesize various azetidine derivatives via suitable nucleophilic substitution reaction. The compound 13 was obtained via two steps of reactions involving the ringopening reaction of ABB (3) with HBr to give 3-bromoazetidine hydrobromide (12) followed by benzyl protection of the N1 group, but this reaction procedure resulted in a low yield (24% total yield).…”
Section: Resultsmentioning
confidence: 99%
“…13 C-NMR spectra were recorded on a JEOL JNM-AL300 (75 MHz) or JEOL JNM-AL400 (100 MHz) spectrometer with complete proton decoupling. Chemical shifts are given in d values (ppm) using tetramethylsilane (TMS) as an internal standard.…”
Section: Methodsmentioning
confidence: 99%
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