Improved method for the synthesis of norfloxacin

Mokrushina, G. A.; Kotovskaya, S. K.; Baskakova, Z. M.; Petrova, G. M.; Kolmakova, T. V.; Charushin, Valery N.; Русинов, В. Л.; Чупахин, О. Н.

doi:10.1007/bf02334643

Cited by 4 publications

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“…The fluorine atom at position 7 of 6,7-difluoro-substituted 4-quinolones 100 can be substituted selectively by a piperazine residue while the fluorine atom at position 6 is not affected [95,96]. If the amine cannot be brought directly into reaction with the 7-fluoro-substituted 4-quinolone, e.g., on account of low nucleophilicity, the approach [98,99] based on the synthesis of the azide 106 and its subsequent reaction with the heterocyclic amines can be used.…”

Section: Insertion Of a Substituent At Position 7 With The Formation mentioning

confidence: 99%

The methods of synthesis, modification, and biological activity of 4-quinolones (review)

Boteva

Красных

2009

Chem Heterocycl Comp

109

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Data on methods for the construction of the 4-quinolone skeleton and modification of the substituents around it are reviewed. The "structure-activity" relationships of 4-quinolones are examined with respect to antibacterial and antitumor activity.Keywords: 4-quinolones, biological activity. 4-Quinolones have been a subject of research for many scientific teams, and this is reflected in the numerous reviews and monographs devoted to various aspects of the subject. One of the early reviews [1] concerns aspects of the synthesis of individual representatives of the group of 4-quinolones and comparative characterization of their antimicrobial activity. Basic approaches to construction of the fluoroquinolone skeleton and also variation of the substituents at various positions of the ring were examined in the review [2]. The relationship between the structure and antibacterial activity is discussed in [3], and methods for the synthesis of polycyclic derivatives of 4-quinolones based on the annelation of rings to the various faces of the quinoline skeleton are discussed in the review [4]. The reviews [5, 6] were devoted to identification of the structural modifications of 4-quinolones responsible for their conversion from antibacterial agents to antitumor agents. The molecular and biological aspects of the antibacterial action of 4-quinolone-3-carboxylic acids are examined in [7], and issues concerned with the clinical application of 4-quinolones are discussed in the reviews [8][9][10][11][12] and in the monograph [13]. The synthesis and the "structure-activity" relationships of the bioisosteres of 4-quinolones -2-pyridones -are examined in the review [14].The aim of the present review was to classify existing methods for the synthesis not only of fluoroquinolones but also of any 4-quinolones, to demonstrate the effects of modification of the molecule at all positions, to summarize data on the various types of activity, and to examine the "structure-activity" relationship with respect to antibacterial and antitumor activity.

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Section: Insertion Of a Substituent At Position 7 With The Formation mentioning

confidence: 99%

The methods of synthesis, modification, and biological activity of 4-quinolones (review)

Boteva

Красных

2009

Chem Heterocycl Comp

109

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“…To demonstrate the utility of these quinolone skeletons in the synthesis of known therapeutic agents, we converted intermediates 6.12 and 6.13 into ciprofloxacin and norfloxacin, respectively, through S N Ar and hydrolysis steps, as shown in Scheme 4. 11,40,41 Similarly, the reaction of 7.7 with piperidine in N-methyl-2-pyrrolidinone at 120°C for ten hours gave the 2-quinolone derivative 9 in 78% isolated yield, demonstrating the possibility of using derivatives such as 6.7-6.10 and 7.7-7.10 to prepare new libraries of quinolones (Scheme 4).…”

Section: -mentioning

confidence: 97%

Direct Transformation of Baylis-Hillman Acetates into N-Substituted Quinolones through an SN2′ → SNAr → (Δ3,4-Δ2,3 Shift) → Oxidation Sequence

Napoleon¹,

Manheri²

2011

Synthesis

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When subjected to tandem S N 2¢-S N Ar cyclization in the presence of alkyl or aralkyl amines, Baylis-Hillman acetates gave the corresponding 1,2-dihydroquinolines, which on simple exposure to light and oxygen afforded the corresponding 4-and 2-quinolones through sensitized oxidation or a D 3,4 -D 2,3 shift → oxidation cascade. The mechanism of the oxidation step, the stabilities of the 1,2-and 1,4-dihydroquinolines in solution and in the solid state, and the synthetic elaboration of the key intermediates to known therapeutic agents are discussed.

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The complexes of metal ions with fluoroquinolones

Serafin

Stańczak

2009

Russ J Coord Chem

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Improved method for the synthesis of norfloxacin

Cited by 4 publications

References 0 publications

The methods of synthesis, modification, and biological activity of 4-quinolones (review)

The methods of synthesis, modification, and biological activity of 4-quinolones (review)

Direct Transformation of Baylis-Hillman Acetates into N-Substituted Quinolones through an SN2′ → SNAr → (Δ3,4-Δ2,3 Shift) → Oxidation Sequence

The complexes of metal ions with fluoroquinolones

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