SYNTHESIS OF SUBSTITUTED QUINOLINE-3-CARBALDEHYDES

Dehalogenation of а series substituted 2-chloroquinoline-3-carbaldehydes was investigated. It was found that zinc dust in alkali ethanol practically do not react with 2-chloro-3-(1,3-dioxolan)-2-yl-7-methylquinolines for a 5 day at ambient temperature. Increase temperature to boiling point of reaction mixture lead to increase yield 7-methylquinoline-3-carbaldehyde to 12.5%. This reaction with 2-chloro-3-dimetoxymetyl-7-methylquinoline give 26.5 above aldehyde. Replacement of ethanol to methanol give only traces of desired aldehyde. Neither 2-chloro-7-methylquinoline-3-carbaldehyde, nor his acetals do not react with sodium dithionite. Furthermore for activation of halogen we replaced chloraldehydes to iodoaldehydes by Finkelstein reaction, then protect aldehyde function by formation of dimethylacetals and treatment his by sodium dithionite in mixture pyridine-water. Desired aldehydes was obtained with poor to moderate yields. Increasing yields of this reaction is goal our further investigations

НОВИЙ ПІДХІД ДО СИНТЕЗУ 5-(4-ЦІАНОФЕНІЛ)-10,15,20-ТРИФЕНІЛПОРФІРИНА

The interaction of diazonium salt of easily accessible 5-(4-aminophenyl)-10,15,20-triphenylporphyrin with hydroiodic acid leads to corresponding 5-(4-iodophenyl)-10,15,20-triphenylporphyrin. Substitute of iodine by cyano group was carried out by treatment of Zn complex of mono-iodophenylporphyrin by copper (I) cyanide in DMF.Взаємодія діазонієвої солі 5-(4-амінофеніл)-10,15,20-трифенілпорфірина з йодистоводневою кислотою призводила до 5-(4-йодфеніл)-10,15,20-трифенілпорфіри-на. Заміну йоду на ціаногрупу здійснювали обробкою цинкового комплексу останнього ціанідом міді (I) у диметилформаміді

СИНТЕЗ ТА ВЛАСТИВОСТІ МЕЗО-ФОРМІЛПОРФІРИНІВ

Взаємодією пірола з сумішшю метилаля та 3,5-дитретбутилбензальдегіда або хі-нолін-6-карбальдегіда з наступним хроматографічним поділом отримані 5-метил-10,15,20-три(3,5-дитретбутилфеніл)-порфірин та 5-метил-10,15,20-три(6-хінолініл)-порфирин. Мезо-метилпорфірини були окислені діоксидом селена до відповідних лезо-формілпорфіринов. Обробкою 5-форміл-10,15,20-три(6-хінолініл)порфірина метиловым эфиром яара-толуолсульфокислоти був вперше отриманий водорозчинний порфірин з альдегідною групою

SYNTHESIS AND PROPERTIES OF STERICALLY HINDERED WATER SOLUBLE PORPHYRINE

5,10,15,20-(2-methoxy-3-quinolinyl)porphyrine, which was a mixture of atropisomers, was obtained by condensation of 2-methoxyquinoline-3-carbaldehyde with pyrrole in propionic acid. Quaternization of nitrogen atoms of peripheric substituents in this compound lead to water soluble sterically hindered porphyrine

SYNTHESIS OF WATER SOLUBLE BACTERIOCHLORINE

Reduction of meso-tetra(6-quinolinyl)porphyrine by diimide, which was obtained by oxydation of hydrazine-hydrate by sodium periodate in mixture pyridine-methanol-water, lead to corresponding bacteriochlorine, which was transformed in water soluble form by quaternization of peripheric substituents by methyl ester of para-toluenesulphonic acid in inert atmosphere

SYNTHESIS OF PORPHYRINS WITH ADDITIONAL COORDINATION SITES ON PERIPHERY OF MACROCYCLE

The metalloporphyrins containing fragments of 1,3-nitroketones on periphery of macrocycle was obtained by nitration of copper complexes of isomeric ketoporphyrins by mixture of nitrogen oxide NO2 and dinitrogene tetroxide N2O4. Catalytic reduction of nitro groups in these compounds by palladium on carbon leads to corresponding 1,3-enaminocetones, which capable to exo-coordination with ions of transition metals

СИНТЕЗ МЕТАЛОКОМПЛЕКСІВ ВОДОРОЗЧИННИХ ДИХІНОЛІНІЛПОРФІРИНІВ – ПОТЕНЦІЙНИХ АНТИМІКРОБНИХ АГЕНТІВ

At present, extensive research is being carried out on the phenomenon of resistance of microbes to antibiotics, including the newest of them. Among the most promising drug candidates for treatment such superbugs is derivatives of 5,15-disubstituted water-soluble porphyrins developed and patented by Destiny Pharma, UK. Here, we continued of our investigation of quinolinylporphyrins and report about synthesis of 5,15-di(n-propyl)-10,20-di(3-quinolinyl)porphyrine and its isomer - 5,10-di(n-propyl)-15,20-di(3-quinolinyl)porphyrine and their complexes with Fe and Mn. The porphyrins was obtained by mixed aldehydes condensation of mixture quinoline-3-carbaldehyde and n-butyraldehyde with pyrrole in propionic acid with small amount propionic anhydride. Above mentioned porphyrins was separated and purified by column chromatography on silica gel and their Fe and Mn complexes was synthesized in refluxing DMF by treatment respectively FeCl3 and Mn(CH3CO2)2. Water-soluble form of the metalloporphyrines was obtained by quaternization of nitrogen atom of quinolinyl substituents by methyl-paratoluenesulfonate for further investigation their antimicrobial properties.Конденсацією піролу з сумішшю н-масляного альдегіду та хінолін 3-карбальдегіду в пропіоновій кислоті отримана суміш порфіринів з н-пропільними та 3-хінолінільними замісниками з якої виділені 5,15-ди(н-пропіл), 10,20-ди(3-хінолініл)порфірин та 5,15-ди(н-пропіл),10,20-ди(3-хінолініл)порфірин. Взаємодією з солями заліза та марганцю в диметилформаміді отримані відповідні металокомплекси, які переведені в водорозчинну форму кватернізацією метиловим естером п-толуенсульфокислоти в нітрометані

Synthesis of metallocomplexes of water soluble bisquinolinylporhyrins as potential antimicrobial agents

At present, extensive research is being carried out on the phenomenon of resistance of microbes to antibiotics, including the newest of them. Among the most promising drug candidates for treatment such superbugs is derivatives of 5,15-disubstituted water-soluble porphyrins developed and patented by Destiny Pharma, UK. Here, we continued of our investigation of quinolinylporphyrins and report about synthesis of 5,15-di(n-propyl)-10,20-di(3-quinolinyl)porphyrine and its isomer - 5,10-di(n-propyl)-15,20-di(3-quinolinyl)porphyrine and their complexes with Fe and Mn. The porphyrins was obtained by mixed aldehydes condensation of mixture quinoline-3-carbaldehyde and n-butyraldehyde with pyrrole in propionic acid with small amount propionic anhydride. Above mentioned porphyrins was separated and purified by column chromatography on silica gel and their Fe and Mn complexes was synthesized in refluxing DMF by treatment respectively FeCl3 and Mn(CH3CO2)2. Water-soluble form of the metalloporphyrines was obtained by quaternization of nitrogen atom of quinolinyl substituents by methyl-paratoluenesulfonate for further investigation their antimicrobial properties

Aminomethanesulfonic Acids as Reaction Products in SO2–NH2Alk–CH2O–H2O Systems: Synthesis and Structure

An original procedure was proposed for the synthesis of a series of aminomethanesulfonic acids AlkNHCH2SO3 (Alk = n-Bu, n-Hept, n-Oct, Bn) and N-tris(hydroxymethyl)methylammonium hydroxymethanesulfonate. The structure of the compounds synthesized was examined by elemental analysis, X-ray diffraction, IR spectroscopy, and mass spectrometry