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

1-R-4-Hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylic acids 2-nitrobenzylidenehydrazides are reduced to the corresponding quinoline-3-carboxamides by zinc in glacial acetic acid but in refluxing triethylphosphite they are converted to the symmetrical N,N′-di(4-hydroxy-2-oxo-1,2-dihydro-3-quinolinoyl)hydrazines. A study of the antitubercular activity of the synthetic compounds has been carried out. __________ Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1687–1692, November, 2007.     

4-hydroxy-2-quinolones. 110. Bromination of 1-r-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylic acid anilides

1-R-4-Hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylic acid anilides have been prepared. It has been shown experimentally that these compounds are brominated by molecular bromine in glacial acetic acid at position 4 of the anilide fragment. The antitubercular properties of the compounds synthesized are discussed. __________ Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1508–1516, October, 2006.     

4-Hydroxy-2-quinolones 126. 1-Hydroxy-3-oxo-5,6-dihydro-3H-pyrrolo[3,2,1-<Emphasis Type="Italic">ij</Emphasis>]quinoline-2-carboxylic acid hydrazide and its derivatives

A preparative method has been developed for the synthesis of 1-hydroxy-3-oxo-5,6-dihydro-3H pyrrolo[3,2,1-ij]quinoline-2-carboxylic acid hydrazide and its derivatives. The results of a study of the antitubercular activity of the synthesized compounds are presented. __________ Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1196–1203, August, 2007.     

4-Hydroxy-2-quinolones. 111. Simple synthesis of 1-substituted 4-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylic acids

A preparative method of obtaining 1-substituted 4-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylic acids is proposed. Features of their spatial structure have been studied. __________ Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 69–74, January, 2007.     

4-Hydroxy-2-quinolones. 108. N-R-amides of 9-fluoro-1-hydroxy-5-methyl-3-oxo-6,7-dihydro-3H,5H-pyrido[3,2,1-ij]quinoline-2-carboxylic acid and their antitubercular activity

The reaction of 6-fluoro-2-methyl-1,2,3,4-tetrahydroquinoline with triethylmethanetricarboxylate gives di(9-fluoro-1-hydroxy-5-methyl-3-oxo-6,7-dihydro-3H,5H-pyrido[3,2,1-ij]quinolin-2-yl)methane and ethyl 9-fluoro-1-hydroxy-5-methyl-3-oxo-6,7-dihydro-3H,5H-pyrido[3,2,1-ij]quinoline-2-carboxylate from which alkyl-, dialkylaminoalkyl-, and hetarylamides as well as hydrazides were prepared. The structure and antitubercular properties of the compounds synthesized are discussed. __________ Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1391–1407, September, 2006.     

4-Hydroxy-2-quinolones 150*. Efficient synthesis,structure, and biological activities of 4-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylic acid alkyl amides

A simple and efficient method for preparing 4-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylic acid alkyl amides is proposed. The results of a study of the diuretic activity of the compounds synthesized are reported. *For communication 149 see [1]. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1841-1848, December, 2008.     

4-Hydroxy-2-quinolones. 97. Simple synthesis of the esters of 4-halo-substituted 2-oxo-1,2-dihydroquinoline-3-carboxylic acids

Short term treatment of 3-ethoxycarbonyl-4-morpholino-2-oxo-1,2-dihydroquinoline with aqueous solutions of hydrohalogen acids leads to the formation of the ethyl esters of 4-halo-substituted 2-oxo-1,2-dihydroquinoline-3-carboxylic acids. Hydrolysis in HF is possible on extended boiling only to the 4-hydroxy derivative. __________ Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 1022–1025, July, 2006.     

4-hydroxy-2-quinolones. 153*. Synthesis of hetarylamides of 4-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylic acid

4-Methyl-2-oxo-1,2-dihydroquinoline-3-carboxylic acid hetarylamides can be prepared by two fundamentally different routes with allowance made for the thermal stability of the starting hetarylamines. * For Communication 152 see [1]. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 426–432, March, 2009.     

4-hydroxy-2-quinolones. 96. Synthesis and properties of 4-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylic acid

Alkaline hydrolysis of the ethyl ester of 4-(cyanoethoxycarbonylmethyl)-2-oxo-1,2-dihydroquinoline-3-carboxylic acid is accompanied by decarboxylation with loss of two molecules of CO₂ and leads to 4-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylic acid. __________ Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 887–893, June, 2006.     

4-Hydroxy-2-quinolones 140. Synthesis and diuretic activity of arylalkylamides of 4-methyl-2-oxo-1,2-dihydro-quinoline-3-carboxylic acid

The interaction of 4-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylic acid with thionyl chloride in oxygen-containing solvents leads to the formation of a significant amount of colored side products, consequently it was proposed the reaction be carried out in carbon tetrachloride. The synthesis of a series of amides was effected by the amidation of the obtained acid chloride with appropriate primary arylalkylamines. Results are presented of a study of the effect of the synthesized compounds on the urine-excreting function of the kidney. __________ Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 78–87, January, 2008.     

4-Hydroxy-2-quinolones. 90. Synthesis and antitubercular activity of 4-methyl-2-thiazolylamides of halo-substituted 4-hydroxy-2-oxo-1,2-dihydro-3-quinolinecarboxylic acids

Several variants were studied for the synthesis of esters of halogen derivatives of 4-hydroxy-2-oxo-1,2-dihydro-3-quinolinecarboxylic acids, whose reaction with 2-amino-4-methylthiazole gives the corresponding hetarylamides. Results are given for a study of the antitubercular activity of these products. Communication 89, see ref. [1]. __________ Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 71–76, January, 2006.     

4-Hydroxy-2-quinolones. 92. Reaction of 1-R-4-chloro-3-ethoxycarbonyl-2-oxo-1,2-dihydroquinolines with anilines

A preparative method is proposed and the synthesis of 4-arylamino-2-oxo-1,2-dihydroquinolines has been effected. An X-ray structural investigation of 4-(4-chlorophenylamino)-2-oxo-1-propyl-1,2-dihydroquinoline-3-carboxylic acid has been carried out enabling the ease of decarboxylating such compounds to be substantiated. Results are given of a study of the anti-inflammatory activity of the synthesized compounds. __________ Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 386–395, March, 2006.     

4-Hydroxy-2-quinolones 138. Synthesis and study of structure-biological activity relationships in a series of 1-hydroxy-3-oxo-5,6-dihydro-3H-pyrrolo[3,2,1-<Emphasis Type="Italic">ij</Emphasis>]quinoline-2-carboxylic acid anilides

Two methods are discussed and the synthesis of a series of 1-hydroxy-3-oxo-5,6-dihydro-3H-pyrrolo[3,2,1-ij]quinoline-2-carboxylic acid anilides has been carried out. The antitubercular activity and the effect on the urinary function of the kidney have been studied for the compounds prepared. A structure-biological activity relationship is discussed. __________ Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1808–1819, December, 2007.     

4-hydroxy-2-quinolones. 109. Alkylation of 4-substituted ethyl 2-oxo-1,2-dihydro-quinoline-3-carboxylates

The alkylation of the ethyl esters of 4-methyl, 4-chloro-, and 4-amino substituted 2-oxo-1,2-dihydroquinoline-3-carboxylic acid by ethyl iodide in the system DMF/K₂CO₃ has been studied. Features of the structure of the starting compounds and their effect on the ratio of the N-and O-alkyl products formed are discussed. __________ Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1502–1507, October, 2006.     

4-Hydroxy-2-quinolones 113. Synthesis and antitubercular activity of N-R-amides of 4-hydroxy-6-methyl-2-oxo-1-propyl-1,2,5,6,7,8-hexahydroquinoline-3-carboxylic acid

A preparative method has been developed and the synthesis has been effected of anilides and heterylamides of 4-hydroxy-6-methyl-2-oxo-1-propyl-1,2,5,6,7,8-hexahydroquinoline-3-carboxylic acid. A comparative analysis has been carried out of the structure and antitubercular properties of the synthesized compounds and their analogs unsubstituted in the quinoline nucleus. __________ Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 405–414, March, 2007.     

4-Hydroxy-2-quinolones 142. 4-Methyl-2-oxo-1,2-dihydroquinoline-3-carboxylic acid anilides as potential diuretics

A large series of 4-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylic acid anilides has been prepared as potential diuretic agents. The effect of all of the synthesized compounds on the urinary function of the kidney has been investigated. The appearance of a “structure — diuretic activity” relationship is discussed. __________ Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 239–245, February, 2008.     

4-hydroxy-2-quinolones. 95. Synthesis, structure, and antitubercular properties of hetarylamides of 4-hydroxy-2-oxo-1,2,5,6,7,8-hexahydroquinoline-3-carboxylic acid

The optimal conditions for obtaining hetarylamides of 4-hydroxy-2-oxo-1,2,5,6,7,8-hexahydroquinoline-3-carboxylic acid are suggested on the basis of derivatographic investigations. The ¹H NMR spectra of the synthesized compounds, their spatial structure, and also the results of a study of their antitubercular properties are discussed. __________ Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 874–886, June, 2006.     

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

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. __________ Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 542–555, April, 2006.     

4-Hydroxy-2-quinolones. 107. Reaction of triethyl methanetricarboxylate with indoline

The first stage of the reaction of triethyl methanetricarboxylate with indoline is the formation of the diethyl ester of 2-(indoline-1-carbonyl)malonic acid, which then, depending on the conditions selected, may be converted into the ethyl ester of 2-(indoline-1-carbonyl)-3-(indolin-1-yl)-3-oxopropionic acid, methanetri-N-(indolin-1-yl)carboxamide, or the ethyl ester or (indolin-1-yl)amide of 1-hydroxy-3-oxo-5,6-dihydro-3H-pyrrolo[3,2,1-ij]quinoline-2-carboxylic acid. __________ Translated From Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1191–1197, August, 2006.     

4-Hydroxy-2-quinolones 120. Synthesis and structure of ethyl 2-hydroxy-4-oxo-4H-pyrido-[1,2-a]pyrimidine-3-carboxylate

An improved method for the preparation and purification of ethyl 2-hydroxy-4-oxo-4H-pyrido[1,2-a]-pyrimidine-3-carboxylates is proposed. According to ¹H and ¹³C NMR spectroscopic data the synthesized compounds exist in DMSO solution in the 2-hydroxy-4-oxo form while in the crystal (at least for the case of the unsubstituted derivative) X-ray analysis shows that it occurs in the bipolar 2,4-dioxo form. __________ Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 864–876, June, 2007.