4-Hydroxyquinolones-2

Украинец, И. В.; Bezuglyi, P. A.; Treskach, V. I.; Kornilov, M. Yu.; Туров, А. В.; Maslennikov, A. I.; Gladchenko, S. V.; Krivobok, V. I.

doi:10.1007/bf00531325

Cited by 9 publications

(9 citation statements)

References 2 publications

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“…After dilution with water (see example of obtaining amide 19c, method A) the reaction mixture was acidified with dilute HCl to pH 3-4 and left at room temperature for 4-5 h. The solid amide 27, which precipitated, was filtered off, washed with water, and dried. Yield A mixing test with a sample of amide 27 obtained by amidation of the ethyl ester of 1-H-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylic acid with propylamine [13] gave no depression of melting point. The 1 H NMR spectra of these compounds were identical.…”

Section: Methodsmentioning

confidence: 99%

“…The amidation of 1-H-4-amino-2-oxo-1,2-dihydroquinoline-3-carboxylic acid (20, Scheme 3) was also unsuccessful. Boiling equimolar quantities of acid and amine in DMF, used successfully in the synthesis of alkylamides of 1-H-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylic acid [13], was accompanied in this case by the decarboxylation of the 4-aminoacid 20 with the formation of 1-H-4-amino-2-oxo-1,2-dihydroquinoline (21).…”

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confidence: 99%

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4-Hydroxy-2-quinolones. 93. Synthesis and biological properties of 2-hydroxy-4-imino-1,4-dihydroquinoline-3-carboxylic acid N-R-amides

Украинец

Сидоренко

Gorokhova

et al. 2006

Chem Heterocycl Compd

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Various methods of synthesizing amides of 2-hydroxy-4-imino-1,4-dihydroquinoline-3-carboxylic acids have been studied. Results of investigations on the antitubercular and antiinflammatory activity of the obtained compounds are discussed.Amides are a class of organic compounds which are rightfully considered to be most convenient for carrying out investigations devoted to the search for rules on structure-pharmacological activity links. The basis for such a conclusion is the fact that the amide group is an important component of many biologically active substances, both natural and synthetic. The enormous variety of methods and procedures used in the synthesis of amides, and also the practically unlimited selection of starting materials, enables systematic changes to be introduced into the structure of the final compounds, thereby purposefully changing their physicochemical and biological properties.Proceeding from this, one of the stages of our investigations was devoted to the amide of 4-amino-2-oxoquinoline-3-carboxylic acids. As one of the proposed variants of obtaining such compounds we studied the possibility of synthesizing amides of 1H-4-chloro-2-oxo-1,2-dihydroquinoline-3-carboxylic acid 1, which then might be transformed into the 4-amino derivative by any suitable method.Previous attempts to obtain amides 1 by the reaction of 4-chloro acid 2a with amines in the presence of N,N'-dicyclohexylcarbodiimide were unsuccessful [2]. Activation of the acid component of acid 2a with N,N'-carbonyldiimidazole (CDI) also gave no positive result. It turned out that on interacting 4-chloro-2-oxo-1,2-dihydroquinoline-3-carboxylic acid (2a) with N,N'-carbonyldiimidazole in anhydrous DMF the vigorous evolution of CO 2 characteristic of this reaction was observed, obviously indicating the formation of acylimidazole 3 (Scheme 1).

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Section: Methodsmentioning

confidence: 99%

Section: + +mentioning

confidence: 99%

4-Hydroxy-2-quinolones. 93. Synthesis and biological properties of 2-hydroxy-4-imino-1,4-dihydroquinoline-3-carboxylic acid N-R-amides

Украинец

Сидоренко

Gorokhova

et al. 2006

Chem Heterocycl Compd

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“…1-R-4-Hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylic Acids Hydrazides 2 were prepared by the method in [16]. ).…”

Section: Methodsmentioning

confidence: 99%

4-Hydroxy-2-quinolones 132. Synthesis, chemical, and biological properties of 1-R-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylic acids 2-nitrobenzylidenehydrazides

Украинец

Сидоренко

Golovchenko

2007

Chem Heterocycl Comp

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“…In all cases DMSO-d 6 was used as solvent and TMS as internal standard. The 1R-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylic acid hydrazides 1a-i were synthesized by our reported method [23].…”

Section: Methodsmentioning

confidence: 99%

4-Hydroxy-2-quinolones 171*. Synthesis, isomerism, and antitubercular activity of 1-R-4-hydroxy-2-oxo-1,2-dihydro-quinoline-3-carboxylic acid alkylidenehydrazides

Украинец

Liu

Ткач

et al. 2009

Chem Heterocycl Comp

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Alkylidenehydrazides have been synthesized by the reaction of 1-R-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylic acid hydrazides with lower dialkyl ketones in order to reveal a structureantitubercular activity relationship. It was shown by 1 H NMR spectroscopy that hydrazones obtained from the unsymmetrical ketone -methyl ethyl ketone -exist primarily in the E-isomer form. It was found that the presence of two aliphatic substituents in the alkylidene fragment of the compounds investigated leads to a marked lowering of antimic obacterial properties. rKeywords: hydrazones, 1-R-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylic acids, isomerism, antitubercular activity.The chemical modification of known medicines is one of the most widely used procedures at this time for the elimination of particular limitations [2]. One of the most significant examples of the success and promise of this route for resolving problems in the discovery and development of more efficient medicines for treating tuberculosis is isoniazid which has been well known for a long time. For more than 50 years this preparation has remained as one of the main chemotherapeutic agents for treatment of different forms of tuberculosis. Additionally, numerous hydrazones were synthesized on its basis by reactions with different aldehydes and ketones, which successfully are used in medical practice [2, 3] and which are characterized by improved pharmaceutical and/or pharmacokinetic properties. What is particularly importantly that new hydrazones are continuosly designed [4][5][6][7][8][9][10][11][12][13][14].

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4-Hydroxyquinolones-2

Cited by 9 publications

References 2 publications

4-Hydroxy-2-quinolones. 93. Synthesis and biological properties of 2-hydroxy-4-imino-1,4-dihydroquinoline-3-carboxylic acid N-R-amides

4-Hydroxy-2-quinolones. 93. Synthesis and biological properties of 2-hydroxy-4-imino-1,4-dihydroquinoline-3-carboxylic acid N-R-amides

4-Hydroxy-2-quinolones 132. Synthesis, chemical, and biological properties of 1-R-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylic acids 2-nitrobenzylidenehydrazides

4-Hydroxy-2-quinolones 171*. Synthesis, isomerism, and antitubercular activity of 1-R-4-hydroxy-2-oxo-1,2-dihydro-quinoline-3-carboxylic acid alkylidenehydrazides

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