Benzimidazo[l,2-a]pyrazolo[l,5-c]quinazoline: a novel heterocyclic system

Lipunova, G. N.; Mokrushina, G. A.; Granovskaya, E. B.; Chasovskikh, O. M.; Charushin, V. N.

doi:10.1070/mc1996v006n01abeh000557

Cited by 12 publications

(8 citation statements)

References 2 publications

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“…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%

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: Type Dmentioning

confidence: 99%

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

Boteva

Красных

2009

Chem Heterocycl Comp

107

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“…When acrylate 179a was heated with TEBAC in acetonitrile, bicyclic derivative 181a was isolated (Scheme 57). 89 Alternative Analogously, room temperature reactions of acrylates 174 with aminoazoles 184 in ethanol give ethyl 3 azolyl amino 2 polyfluorobenzoylacrylates 185, which undergo cyclization in boiling acetonitrile in the presence of KF. For instance, 1 substituted quinolone 186 is obtained from ethyl 2 pentafluoro 3 (pyrazol 3 yl)aminobenzoyl acrylate 185b.…”

Section: Polyfluorobenzoyl Isothiocyanatesmentioning

confidence: 99%

“…This ester is Room temperature reactions of ethyl 3 ethoxy 2 [tetra (penta)fluorobenzoyl]acrylates 174a,b with heterylhydr azines in toluene yield compounds 179a-g (Scheme 57). 89 The tendency of the latter toward amino imine tauto merism allows cyclization with [i,j] annulation of quino lines to the triazine ring. Pentacyclic derivatives 180a-g are obtained by cyclization of acrylates 179a-g in boiling acetonitrile in the presence of DBU, triethylbenzyl ammonium chloride (TEBAC), or KF, or by heating in dioxane in the presence of NaH.…”

Section: Polyfluorobenzoyl Isothiocyanatesmentioning

confidence: 99%

Fluoroarenes in the synthesis of benzoannulated nitrogen-containing heterocycles

Layeva¹,

Носова²,

Lipunova³

et al. 2008

Russ Chem Bull

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“…In the reaction of 3-acetyl (benzoyl)-substituted 5-oxo-7,8-difluoro-5,9a-dihydropyrazolo[1,5-a]quinolin-4-carboxylates and 5-methoxy derivative 91 with bromine, the ipsosubstitution of acetyl (benzoyl) group takes place [85,86]. [93,94].…”

Section: Scheme 22mentioning

confidence: 99%