Nitroquinolones with broad-spectrum antimycobacterial activity in vitro

Artico, M.; Mai, Antonello; Sbardella, Gianluca; Massa, S.; Montaldo, Chiara; Lostia, Stefania; Demontis, Francesca; Colla, Paolo La

doi:10.1016/s0960-894x(99)00251-6

Cited by 23 publications

(21 citation statements)

References 13 publications

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“…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. The insertion of phenyl, p-nitrophenyl [73], benzyl [13], and morpholinyl [110] substituents has an unfavorable effect.…”

Section: Methodsmentioning

confidence: 99%

“…The insertion of Hal [13], NO 2 [64], and NH 2 [60] at position 6 is favorable. The substituents can be arranged in the following order of increasing activity: F > H > NH 2 > Me > Br [13].…”

Section: Methodsmentioning

confidence: 99%

“…The cyclization of compounds 28 leading to the formation of 4-quinolones 29 can be realized in the presence of various reagents: sodium ethoxide in ethanol [61]; KF in DMF [60]; K 2 CO 3 or Li 2 CO 3 in DMF [26,55,56,58,60,[62][63][64] or acetonitrile or NaH in dioxane [57] or THF [62]; triethylamine in DMF [65], DMSO [59], or toluene [57,59,60].…”

Section: Type Dmentioning

confidence: 99%

“…Tricyclic compounds containing a 4-quinolone fragment [61], analogs of ofloxacin [63], and pentacyclic derivatives [66] can also be obtained by this method. At position 3 of the 4-quinolones there is usually a carboxyl or alkoxycarbonyl group [55,56,60,[63][64][65][66][67], although there may be a nitro group [59], a CN group [68], or H [58,69]. Moreover, the scheme can also used to obtain the quite rare 2-substituted 4-quinolones (carboxyl group [69], trifluoromethyl group [58]).…”

Section: Type Dmentioning

confidence: 99%

“…64 F + Attempts to bring the quinolone 62 into reaction with phenylhydrazine in ether were unsuccessful, while in alcohol they gave a mixture of unidentified substances [86].…”

mentioning

confidence: 99%

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

Boteva

Красных

2009

Chem Heterocycl Comp

107

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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: Type Dmentioning

confidence: 99%

Section: Type Dmentioning

confidence: 99%

“…64 F + Attempts to bring the quinolone 62 into reaction with phenylhydrazine in ether were unsuccessful, while in alcohol they gave a mixture of unidentified substances [86].…”

mentioning

confidence: 99%

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

Boteva

Красных

2009

Chem Heterocycl Comp

107

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ChemInform Abstract: Nitroquinolones with Broad‐Spectrum Antimycobacterial Activity in vitro.

et al. 1999

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Fighting tuberculosis: An old disease with new challenges

et al. 2005

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Tuberculosis (TB) caused by Mycobacterium tuberculosis remains a leading cause of mortality worldwide into 21st century. The mortality and spread of this disease has further been aggravated because of synergy of this disease with HIV. A number of anti-TB drugs are ineffective against this disease because of development of resistance strains. Internationally efforts are being made to develop new anti-tubercular agents. A number of drug targets from cell wall biosynthesis, nucleic acid biosynthesis, and many other biosynthetic pathways are being unraveled throughout the world and are being utilized for drug development. In this review, socioeconomic problems in developing countries, efforts to control this disease in different individuals, the targets (known already and newly discovered), existing anti-tubercular agents including natural products and lead molecules, and the future prospects to develop new anti-TB agents are described.

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Nitroquinolones with broad-spectrum antimycobacterial activity in vitro

Cited by 23 publications

References 13 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)

ChemInform Abstract: Nitroquinolones with Broad‐Spectrum Antimycobacterial Activity in vitro.

Fighting tuberculosis: An old disease with new challenges

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