ChemInform Abstract: Polycyclic Fluoroquinolinones

Mokrushina, G. A.; Nosova, E. V.; Lipunova, G. N.; Charushin, V. N.

doi:10.1002/chin.200037272

Cited by 8 publications

(12 citation statements)

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“…The effect of substituents at certain positions is unequivocal (3,4), while at certain positions, e.g., 6, it depends on the substituent at position 8. Thus, an unfavorable substituent at position 6 will be advantageous with the "right" substituents at positions 1, 3, and 8 [5].…”

Section: Methodsmentioning

confidence: 99%

“…Replacement of the N atom by an O or C atom deactivates the molecule [4]. The best is an ethyl group at the N atom and also its bioisosteres -cyclopropyl [64, 102-104, 110, 116], tert-butyl [64], methylamino, 2,(4)-(di)fluorophenyl, p-hydroxyphenyl [3], fluorocyclopropyl [97,13], 5-amino-2,4-difluorophenyl, 5-fluoro-2-pyridinyl, 2-amino-3,5-difluoro-2-pyridinyl [13], piperidinyl, piperazinyl [110], and 4-amino-2-fluorophenyl [73] substituents.…”

Section: Methodsmentioning

confidence: 99%

“…In addition, active researches have been carried out on other types of biological activity in 4-quinolones. The following types of activity have been observed in a series of papers: Antiviral with respect to hepatitis B, C, and HIV viruses [3,4,24] and herpes viruses [3,37], antiallergic [3], antimalarial [68,109], antitubercular [36,39,110], immunomodulating [38], antihypoxic [25], antidiabetic [46]. 4-Quinolones have antithrombocytic [111] and positive cardiotonic activity [24].…”

Section: Biological Activity Of 4-quinolonesmentioning

confidence: 98%

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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: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Biological Activity Of 4-quinolonesmentioning

confidence: 98%

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

Boteva

Красных

2009

Chem Heterocycl Comp

109

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“…2-Mercapto-5,6-difluorobenzimidazole 1 was shown to react with aromatic α-haloketones to give 2-phenacylthio-5,6-difluorobenzimidazoles 2. The latter were transformed by acylation and cyclodehydration in an acetic anhydride-pyridine system into benzo [4,5] [13]. Biological tests revealed that compound 4 (Ar = C 6 H 5 ) displayed a considerable activity toward the meastle virus [14].…”

Section: Fluorinated Benzazolesmentioning

confidence: 98%

“…have been advanced [2]. A great deal of publications focus on structural modifications of fluoroquinolones as inhibitors of the DNA-gyrase (bacterial topoisomerase), the enzyme that is responsible for cleavage and renovation of the double helix of bacterial DNA [3][4][5]. It has been shown that fluoroquinolones can influence the eucariot cells, sometimes showing a high cytotoxicity, and thus being of interest as anticancer agents [6,7].…”

Section: Introductionmentioning

confidence: 99%