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Носова, Э. В.; Sidorova, L. P.; Lipunova, G. N.; Mochul’skaya, N. N.; Chasovskikh, O. M.; Charushin, Valery N.

doi:10.1023/a:1020965312463

Cited by 9 publications

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“…In toluene in the presence of potassium carbonate compounds 67 undergo intramolecular cyclization with participation of the oxygen atom of the amide group, leading to the formation of an oxadiazine ring in the tricyclic 4-quinolone 68 [87].…”

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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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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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“… General approaches to the formation of functional derivatives of FQs [ 25 , 26 , 27 , 28 , 29 , 30 , 31 , 32 , 33 , 34 , 35 , 36 , 37 , 38 , 39 , 40 , 41 , 42 , 43 , 44 , 45 , 46 , 47 , 48 , 49 , 50 , 51 , 52 , 53 , 54 , 55 , 56 , 57 , 58 , 59 , 60 , 61 , 62 , 63 ]. …”

Section: Figures Schemes and Tablementioning

confidence: 99%

“…They can be introduced into C-3 via the formation of different functional derivatives of carboxylic acids that are presented in Scheme 1 . For instance, alkylation offers an opportunity to further obtain hydrazine derivatives [ 25 , 26 , 27 , 28 , 29 , 30 , 31 , 32 , 33 , 34 , 35 , 36 , 37 , 38 , 39 , 40 , 41 , 42 , 43 , 44 , 45 , 46 , 47 , 48 , 49 , 50 , 51 , 52 , 53 , 54 , 55 ]. The carboxylic group can be easily turned into an amide group with the subsequent formation of nitriles [ 56 ].…”

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confidence: 99%

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A Comprehensive Review on Chemical Synthesis and Chemotherapeutic Potential of 3-Heteroaryl Fluoroquinolone Hybrids

et al. 2023

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Fluoroquinolones have been studied for more than half a century. Since the 1960s, four generations of these synthetic antibiotics have been created and successfully introduced into clinical practice. However, they are still of interest for medicinal chemistry due to the wide possibilities for chemical modification, with subsequent useful changes in the pharmacokinetics and pharmacodynamics of the initial molecules. This review summarizes the chemical and pharmacological results of fluoroquinolones hybridization by introducing different heterocyclic moieties into position 3 of the core system. It analyses the synthetic procedures and approaches to the formation of heterocycles from the fluoroquinolone carboxyl group and reveals the most convenient ways for such procedures. Further, the results of biological activity investigations for the obtained hybrid pharmacophore systems are presented. The latter revealed numerous promising molecules that can be further studied to overcome the problem of resistance to antibiotics, to find novel anticancer agents and more.

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“…7-Pyrrolidino-4-oxo-6-fluoro-1,4-dihydroquinoline- 3-carboxylic acid hydrazide (Ij) was obtained using a method developed in [15]. The synthesis of previously unreported compounds Ia -Ic, Ik, Il, and IIh is described below.…”

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Fluorinated quinolones possessing antituberculous activity

Lipunova¹,

Носова²,

Кравченко³

et al. 2004

Pharm Chem J

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In recent years, statistics have shown a considerable increase in the incidence of tuberculosis, which has reached one of the first places with respect to lethality among patients with infectious diseases [1]. The rapid development of drug resistance in microbes, the toxicity and side effects of the existing antituberculous agents, and the lack of bactericidal preparations effective against stable mycobacteria -all these factors stimulate the effort directed toward the search for and development of new drugs.An important group of modern antibacterial drugs, so-called fluoroquinolones, is represented by synthetic derivatives of 4-oxo-6-fluoro-1,4-dihydroquinoline-3-carboxylic acid [2 -4]. Thorough investigation into the properties of fluoroquinolones, especially those with polycyclic structures, revealed some new features of their biological activity spectrum such as antitumor and antiviral properties, including activity with respect to hepatitis C and HIV infection [5 -7]. Since some derivatives of ofloxacin and ciprofloxacin have demonstrated high tuberculostatic properties [8,9], it would be expedient to continue the search for new antituberculous agents in this group of compounds.Previously, we have developed methods for the synthesis of fluoroquinolonecarboxylic acid derivatives of types I -III [10 -12]. This paper presents the results of characterization of a series of such compounds with respect to their tuberculostatic activity.(R 1 , R 2 , R 3 , R 4 , and X are specified in Tables 1 and 2).Quinolones I were obtained using a scheme analogous to that of pefloxacin synthesis, via modification of the initial structure at positions 1, 3, and 7. In particular, quinolonecarboxylic acid Ia, containing the (7-fluoroquinoxalin-6-yl)-amino group in position 1, was obtained by heating 3-ethoxy-2-tetrafluorobenzoylacrylic acid ethyl ester with a hydrazine derivative of quinoxaline in toluene, followed by hydrolysis of the ester group on heating in a mixture of hydrochloric and acetic acids, and by substitution of the pyrrolidine residue for the fluorine atom at position 7. Compounds Ih, Ii, Ik, and Il were synthesized in the same way proceeding from the corresponding acrylates. 3-(4-Dimethylaminophenylmethinimino)carbamoyl derivative Ib was obtained via interaction of 7-morpholino-6-fluoro-1-ethyl-4-oxo-1,4-dihydroquinoline-3-carboxylic acid hydrazide with p-dimethylaminobenzaldehyde. 6-Fluoroquinolone Ic (containing the 1,2,3-triazoline fragment in position 7) was obtained via the reaction of 1,3-dipolar cycloaddition of cyclopentanone enamine to 7-azido-6-fluoro-4-oxoquinoline-3-carboxylic acid ethyl ester (see experimental part below). 7-Isoxazolidinyl-substituted 4-oxo-6-fluoro-1,4-dihydroquinoline-3-carboxylic acids (Id -Ig) were synthesized via the reactions of 1,3-dipolar cycloaddition of 4-oxo-6-fluoro-1-ethyl-1,4-dihydroquinoline-3-carboxylic acid 7-azomethinoxide with various unsaturated compounds as described in [11].The synthesis of annelated 1,3,4-thia(oxa)diazino[6,5,4-i, j ]quinolones (II, III) was base...

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Cited by 9 publications

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

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

A Comprehensive Review on Chemical Synthesis and Chemotherapeutic Potential of 3-Heteroaryl Fluoroquinolone Hybrids

Fluorinated quinolones possessing antituberculous activity

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