New 7‐substituted quinolone antibacterial agents. <b>II</b>. The synthesis of 1‐ethyl‐1,4‐dihydro‐4‐oxo‐7‐(pyrazolyl, isoxazolyl, and pyrimidinyl)‐1,8‐naphthyridine and quinolone‐3‐carboxylic acids

Domagala, John M.; Peterson, P.K.

doi:10.1002/jhet.5570260445

Cited by 23 publications

(8 citation statements)

References 12 publications

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“…The previous procedures to introduce nucleophiles at C-7 involved using DMF, DMSO, pyridine and heating at very high temperature [10]. This involves harsh conditions, long times and produced low yields, due to difficulties in separation and purification.…”

Section: Introduction Of Primary Amine Appendages At C-7mentioning

confidence: 99%

Synthesis and Antibacterial Properties of New 8-Nitrofluoroquinolone Derivatives

et al. 2007

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Abstract:The objective of this research was the preparation of new 8-nitrofluoroquinolone models and investigation of their antibacterial properties. The work initially involved large scale preparation of the synthon 7-chloro-1-cyclopropyl-6-fluoro-8-nitro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (3), followed by introduction of substituted primary amine appendages at the C-7 position to give derivatives 9a-g, in which the amino group is appended to substituted benzenes or aromatic heterocycles, is part of a primary α-amino acid or just a simple primary aliphatic amine. This nucleophilic aromatic substitution step was a very simple procedure since the 8-nitro group of the above synthon facilitated the addition of weak nucleophiles at C-7. All compounds prepared were fully identified and characterized using NMR, IR, EA and MS, and were consistent with expected structures. The prepared targets and the intermediates have shown interesting antibacterial activity against gram positive and/or gram negative strains. In particular, the p-toluidine, p-chloroaniline and aniline derivatives showed good activity against S. aureus with MIC range ≈ 2-5 µg/mL. In conclusion, more lipophilic groups seem to enhance activity against gram positive strains. Molecules 2007, 12 1241

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Section: Introduction Of Primary Amine Appendages At C-7mentioning

confidence: 99%

Synthesis and Antibacterial Properties of New 8-Nitrofluoroquinolone Derivatives

et al. 2007

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“…512 ± 524 For example, esters of nalidixic acid (276) were used for this purpose. 523,524 The reactions of these esters with tert-butoxybisdimethylaminomethane in Bu t OH produce enamines 277. The addition of the Vilsmeier reagent derived from DMF and thionyl chloride leads to the formation of enamines 278.…”

Section: Reactions Of 18-naphthyridine Derivativesmentioning

confidence: 99%

“…Treatment of the reaction mixture with hydrazine hydrate, hydroxylaminosulfonic acid or guanidine followed by hydrolysis of the reaction mixture gives rise to pyrazolyl- (279), isoxazolyl-(280) and pyrimidinyl-4-oxo-1,4dihydro-1,8-naphthyridine-3-carboxylic acid derivatives (281). 524 N N…”

Section: Reactions Of 18-naphthyridine Derivativesmentioning

confidence: 99%

Chemistry and biological activities of 1,8-naphthyridines

Литвинов¹

2004

Russ. Chem. Rev.

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“…Compound 2, as well as the other derivatives bearing a l,2,3,6-tetrahydro-4-pyridinyl or a 3-amino-l-cyclopentenyl substituent at C-7, were also prepared by a more convergent methodology involving a palladium-catalyzed cross-coupling of a 7-quinolyltriflate or a 7-chloro-l,8naphthyridine with the cyclic vinylstannanes 16 and 21. The syntheses of these novel tin reagents and their crosscoupled products have already been reported and are outlined in Schemes II and III.18"20 It is noteworthy that, for the preparation of naphthyridines 4-7, the 7-chloro substrate (e.g., 23) proved to be sufficiently reactive that it made unnecessary the formation of the corresponding triflate derivative.…”

Section: Chemistrymentioning

confidence: 99%

Quinolone antibacterials: synthesis and biological activity of carbon isosteres of the 1-piperazinyl and 3-amino-1-pyrrolidinyl side chains

Laborde¹,

Kiely²,

Culbertson³

et al. 1993

J. Med. Chem.

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A series of 6-fluoro-1,4-dihydro-4-oxo-3-quinoline- and 1,8-naphthyridinecarboxylic acids, substituted at the 7-position with carbon-linked side chains, was synthesized and evaluated for antibacterial activity and DNA-gyrase inhibition. Structural modifications focused on replacement of the heterocyclic nitrogen of the frequently found 1-piperazinyl and 3-amino-1-pyrrolidinyl side chains by an sp2- or an sp3-hybridized carbon. All new compounds displayed high in vitro and in vivo antibacterial activity. Potency relative to the standard nitrogenated agents was dependent on ring size and hybridization of the linking carbon atom of the side chain. Compounds with a 1,2,3,6-tetrahydro-4-pyridinyl substituent at C-7 were equipotent with their 1-piperazinyl analogs, whereas those having a 4-piperidinyl or a 3-amino-1-cyclopentenyl ring at C-7 were less active than the 1-piperazinyl or 3-amino-1-pyrrolidinyl substituted agents, respectively. This relative difference in antibacterial potency did not correlate with the observed activity against gyrase, where the majority of the new compounds were equally or more potent than their nitrogenated counterparts.

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New 7‐substituted quinolone antibacterial agents. II. The synthesis of 1‐ethyl‐1,4‐dihydro‐4‐oxo‐7‐(pyrazolyl, isoxazolyl, and pyrimidinyl)‐1,8‐naphthyridine and quinolone‐3‐carboxylic acids

Cited by 23 publications

References 12 publications

Synthesis and Antibacterial Properties of New 8-Nitrofluoroquinolone Derivatives

Synthesis and Antibacterial Properties of New 8-Nitrofluoroquinolone Derivatives

Chemistry and biological activities of 1,8-naphthyridines

Quinolone antibacterials: synthesis and biological activity of carbon isosteres of the 1-piperazinyl and 3-amino-1-pyrrolidinyl side chains

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