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A N Maslivets - One of the best experts on this subject based on the ideXlab platform.
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Synthesis of Imidazole Spiro Compounds From 5-Alkoxycarbonyl-1H-Pyrrole-2,3-Diones and Phenylurea
Chemistry of Heterocyclic Compounds, 2016Co-Authors: Aleksei Yu. Dubovtsev, P S Silaichev, E S Denislamova, Maksim V. Dmitriev, A N MaslivetsAbstract:5-Alkoxycarbonyl-substituted 1 H -pyrrole-2,3-diones react with phenylurea, forming alkyl 4-hydroxy-5-oxo-2-[(phenylcarbamoyl)amino]-2,5-dihydro-1 H -Pyrrole-2-Carboxylates, which cyclize in the presence of sodium methoxide, giving 8-hydroxy-3-phenyl-1,3,6-triazaspiro[4.4]-non-8-ene-2,4,7-triones. The crystal structures of 8-hydroxy-9-(4-methylbenzoyl)-3-phenyl-6-( p -tolyl)-1,3,6-triazaspiro[4.4]non-8-ene-2,4,7-trione and methyl 8-hydroxy-2,4,7-trioxo-3,6-diphenyl-1,3,6-triazaspiro[4.4]non-8-ene-9-carboxylate were studied.
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Reaction of methyl 3-aroyl-1-aryl-4,5-dioxo-4,5-dihydro-1H-Pyrrole-2-Carboxylates with arylhydrazines. synthesis of isomeric 5-arylcarbamoyl-4-aroyl- and 5-aryl-4-aryloxamoyl-1H-pyrazoles
Russian Journal of Organic Chemistry, 2016Co-Authors: A. Yu. Dubovtsev, Maksim V. Dmitriev, A. A. Moroz, A N MaslivetsAbstract:Methyl 3-aroyl-1-aryl-4,5-dioxo-4,5-dihydro-1H-Pyrrole-2-Carboxylates reacted with arylhydrazines to give methyl 3-aroyl-1-aryl-2-(2-arylhydrazinyl)-4-hydroxy-5-oxo-2,5-dihydro-1H-Pyrrole-2-Carboxylates which underwent thermal recyclization into isomeric methyl 1-aryl-5-(arylcarbamoyl)-4-aroyl-1H-pyrazole- 3-carboxylates and methyl 1,5-diaryl-4-[2-oxo-2-(arylamino)acetyl]-1H-pyrazole-3-carboxylates.
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Synthesis of spiro[imidazole-2,2′-pyrroles] by reaction of 4,5-dioxo-4,5-dihydro-1H-Pyrrole-2-Carboxylates with urea
Russian Journal of Organic Chemistry, 2016Co-Authors: A. Yu. Dubovtsev, P S Silaichev, Z G Aliev, M. A. Zheleznova, A N MaslivetsAbstract:Substituted alkyl 4,5-dioxo-4,5-dihydro-1H-Pyrrole-2-Carboxylates reacted with urea to give alkyl 2-(carbamoylamino)-4-hydroxy-5-oxo-2,5-dihydro-1H-Pyrrole-2-Carboxylates which underwent intramolecular cyclization to 8-hydroxy-1,3,6-triazaspiro[4.4]non-8-ene-2,4,7-triones by the action of sodium methoxide.
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Five-membered dioxo heterocycles: CIV. Reaction of methyl 1-aryl-3-benzoyl-4,5-dioxo-4,5-dihydro-1H-Pyrrole-2-Carboxylates with cyclic enehydrazines. Crystal and molecular structure of N-[3′-benzoyl-1′-(4-chlorophenyl)-4′-hydroxy-6,6-dimethyl-2,4,5′-
Russian Journal of Organic Chemistry, 2014Co-Authors: E S Denislamova, Z G Aliev, A N MaslivetsAbstract:Methyl 1-aryl-3-benzoyl-4,5-dioxo-4,5-dihydro-1H-Pyrrole-2-Carboxylates reacted with N′-(5,5-dimethyl-3-oxocyclohex-1-en-1-yl)benzohydrazides and N′-(5,5-dimethyl-3-oxocyclohex-1-en-1-yl)-2,2-diphenylacetohydrazide to give substituted N-[1′-aryl-3′-benzoyl-4′-hydroxy-6,6-dimethyl-2,4,5′-trioxo-1′,4,5,5′,6,7-hexahydrospiro[indole-3,2′-pyrrol]-1(2H)-yl]benz- and -diphenylacetamides.
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Five-membered dioxoheterocycles: XCIX. Reaction of 1-aryl-4-aroyl-5-methoxycarbonyl-1H-pyrrole-2,3-diones with indoles. Crystal and molecular structure of substituted 2-(indol-3-yl)pyrrole
Russian Journal of Organic Chemistry, 2014Co-Authors: E S Denislamova, P A Slepukhin, A N MaslivetsAbstract:1-Aryl-4-aroyl-5-methoxycarbonyl-1 H -pyrrole-2,3-diones react with indole and 2-methylindole with the formation of methyl 1-aryl-3-aroyl-4-hydroxy-2-(1 H -indol-3-yl)-5-oxo-2,5-dihydro-1 H -Pyrrole-2-Carboxylates. Crystal and molecular structure of methyl 3-benzoyl-4-hydroxy-2-(2-methyl-1 H -indol-3-yl)-5-oxo-1-phenyl-2,5-dihydro-1 H -Pyrrole-2-Carboxylate was examined.
Alison Thompson - One of the best experts on this subject based on the ideXlab platform.
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Synthesis and reactivity of 2-thionoester pyrroles: a route to 2-formyl pyrroles
RSC Advances, 2019Co-Authors: Min Joon Kim, Sophie M. Gaube, Michael H. R. Beh, Craig D. Smith, Alison ThompsonAbstract:2-Functionalised pyrroles exhibit considerable synthetic utility. Herein, the synthesis and reactivity of 2-thionoester (–C(S)OR) pyrroles is reported. 2-Thionoester pyrroles were synthesised using a Knorr-type approach from aliphatic starting materials. 2-Thionoester pyrroles were reduced to the corresponding 2-formyl pyrroles, or the deuterated formyl variant, in one step using RANEY® nickel, thereby removing the need for the much-utilised hydrolysis/decarboxylation/formylation steps that are typically required to convert Knorr-type 2-carboxylate pyrroles into 2-formyl pyrroles. 2-Thionoester pyrroles proved tolerant of typical functional group interconversions for which the parent 2-carboxylate pyrroles have become known.
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Thionation reactions of 2-pyrrole carboxylates
RSC Advances, 2016Co-Authors: Brandon R. Groves, Deborah A. Smithen, T. Stanley Cameron, Alison ThompsonAbstract:Reaction of 2-pyrrole carboxylates with Lawesson's reagent at elevated temperatures results in the corresponding thionoesters, concurrent with the production of a new class of pyrrole annulated with the (1,3,2)-thiazaphospholidine unit. X-ray crystallography was used to identify the pyrrolic thiazaphospholidine, which was found to have unique structural features compared to literature analogues. Addition of BF3·OEt2 to the thionation procedure was found to produce the corresponding F-BODIPY, constituting a four-step reaction in one-pot. The scope and limitations of these reactions involving the promiscuous Lawesson's reagent are discussed herein.
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Microwave-Accelerated Synthesis of Benzyl 3,5-Dimethyl-Pyrrole-2-Carboxylate.
ChemInform, 2007Co-Authors: Jasmine Regourd, Ian M. Comeau, Cory S. Beshara, Alison ThompsonAbstract:Benzyl 3,5-dimethyl-Pyrrole-2-Carboxylate, a very useful pyrrole in porphyrin and dipyrromethene synthesis, can be synthesized via the Knorr-type reaction, but in low yield. Alternative routes to benzyl 3,5-dimethyl-Pyrrole-2-Carboxylate have been developed involving the trans-esterification of ethyl 3,5-dimethyl-Pyrrole-2-Carboxylate and the de-acetylation of benzyl 4-acetyl-3,5-dimethyl-2-carboxylate, both precursors being easily obtained using the Knorr reaction. These traditional methods involve treatment of the known products with a strong basic solution or heating for extended periods which often lead to decomposition. The use of microwave energy to promote these two reactions proves to be an extremely efficient way to obtain benzyl 3,5-dimethyl-Pyrrole-2-Carboxylate quickly, in high yield, and in excellent purity with no need for recrystallization. Of particular note is the use of catalytic sodium methoxide in benzyl alcohol, rather than stoichiometric amounts of sodium benzoxide, to effect benzylation.
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Microwave‐accelerated synthesis of benzyl 3,5‐dimethyl‐pyrrole‐2‐carboxylate
Journal of Heterocyclic Chemistry, 2006Co-Authors: Jasmine Regourd, Ian M. Comeau, Cory S. Beshara, Alison ThompsonAbstract:Benzyl 3,5-dimethyl-Pyrrole-2-Carboxylate, a very useful pyrrole in porphyrin and dipyrromethene synthesis, can be synthesized via the Knorr-type reaction, but in low yield. Alternative routes to benzyl 3,5-dimethyl-Pyrrole-2-Carboxylate have been developed involving the trans-esterification of ethyl 3,5-dimethyl-Pyrrole-2-Carboxylate and the de-acetylation of benzyl 4-acetyl-3,5-dimethyl-2-carboxylate, both precursors being easily obtained using the Knorr reaction. These traditional methods involve treatment of the known products with a strong basic solution or heating for extended periods which often lead to decomposition. The use of microwave energy to promote these two reactions proves to be an extremely efficient way to obtain benzyl 3,5-dimethyl-Pyrrole-2-Carboxylate quickly, in high yield, and in excellent purity with no need for recrystallization. Of particular note is the use of catalytic sodium methoxide in benzyl alcohol, rather than stoichiometric amounts of sodium benzoxide, to effect benzylation.
Z G Aliev - One of the best experts on this subject based on the ideXlab platform.
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Synthesis of spiro[imidazole-2,2′-pyrroles] by reaction of 4,5-dioxo-4,5-dihydro-1H-Pyrrole-2-Carboxylates with urea
Russian Journal of Organic Chemistry, 2016Co-Authors: A. Yu. Dubovtsev, P S Silaichev, Z G Aliev, M. A. Zheleznova, A N MaslivetsAbstract:Substituted alkyl 4,5-dioxo-4,5-dihydro-1H-Pyrrole-2-Carboxylates reacted with urea to give alkyl 2-(carbamoylamino)-4-hydroxy-5-oxo-2,5-dihydro-1H-Pyrrole-2-Carboxylates which underwent intramolecular cyclization to 8-hydroxy-1,3,6-triazaspiro[4.4]non-8-ene-2,4,7-triones by the action of sodium methoxide.
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Five-membered dioxo heterocycles: CIV. Reaction of methyl 1-aryl-3-benzoyl-4,5-dioxo-4,5-dihydro-1H-Pyrrole-2-Carboxylates with cyclic enehydrazines. Crystal and molecular structure of N-[3′-benzoyl-1′-(4-chlorophenyl)-4′-hydroxy-6,6-dimethyl-2,4,5′-
Russian Journal of Organic Chemistry, 2014Co-Authors: E S Denislamova, Z G Aliev, A N MaslivetsAbstract:Methyl 1-aryl-3-benzoyl-4,5-dioxo-4,5-dihydro-1H-Pyrrole-2-Carboxylates reacted with N′-(5,5-dimethyl-3-oxocyclohex-1-en-1-yl)benzohydrazides and N′-(5,5-dimethyl-3-oxocyclohex-1-en-1-yl)-2,2-diphenylacetohydrazide to give substituted N-[1′-aryl-3′-benzoyl-4′-hydroxy-6,6-dimethyl-2,4,5′-trioxo-1′,4,5,5′,6,7-hexahydrospiro[indole-3,2′-pyrrol]-1(2H)-yl]benz- and -diphenylacetamides.
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five membered 2 3 dioxo heterocycles lxxx recyclization of 1h pyrrole 2 3 diones into pyrazolo 1 5 a pyrimidines by the action of pyrazolamine crystalline and molecular structure of substituted pyrazolo 1 5 a pyrimidine
Russian Journal of Organic Chemistry, 2011Co-Authors: E S Denislamova, N V Bubnov, Z G AlievAbstract:Methyl 1-aryl-3-aroyl-4,5-dioxo-4,5-dihydro-1H-Pyrrole-2-Carboxylates reacted with 3-methyl-4-phenyl-1H-pyrazol-5-amine to give methyl 7-arylcarbamoyl-6-aroyl-2-methyl-3-phenylpyrazolo[1,5-a]-pyrimidine-5-carboxylates. The molecular and crystalline structures of methyl 6-benzoyl-7-(4-chlorophenylcarbamoyl)-2-methyl-3-phenylpyrazolo[1,5-a]pyrimidine-5-carboxylate were studied by X-ray analysis.
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five membered 2 3 dioxo heterocycles lxx spiro heterocyclization of 1h pyrrole 2 3 diones by the action of 1 5 binucleophiles crystalline and molecular structure of ethyl 1 benzyl 7 methoxy 3 3 dimethyl 1 2 dioxo 5 phenyl 1 2 2 3 4 10 hexahydro 1h sp
Russian Journal of Organic Chemistry, 2010Co-Authors: P S Silaichev, M V Dmitriev, Z G Aliev, A N MaslivetsAbstract:Ethyl 1-alkyl-4,5-dioxo-2-phenyl-4,5-dihydro-1H-pyrrole-3-carboxylates reacted with 3-arylamino-5,5-dimethylcyclohex-2-en-1-ones as carbon-centered 1,5-binucleophiles to give the corresponding substituted ethyl 1′-alkyl-3,3-dimethyl-1,2′-dioxo-5′-phenyl-1′,2,2′,3,4,10-hexahydro-1H-spiro[acridine-9,3′-pyrrole]-4′-carboxylates whose structure was proved by X-ray analysis.
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five membered 2 3 dioxoheterocycles lxvii pyrroledione pyrroledion recyclization of isopropyl 2 1 aryl 4 5 dioxo 2 phenyl 4 5 dihydro 1h pyrrol 3 yl 2 oxoacetates under the action of arylamines crystal and molecular structure of z isopropyl 2 hydroxy
Russian Journal of Organic Chemistry, 2010Co-Authors: P S Silaichev, M V Dmitriev, Z G AlievAbstract:Reactions of isopropyl 2-(1-aryl-4,5-dioxo-2-phenyl-4,5-dihydro-1H-pyrrol-3-yl)-2-oxoacetates with aromatic amines involve a pyrroledione-pyrroledione recyclization to form isopropyl 1-aryl-2-hydroxy-4,5-dioxo-3-[phenyl(arylamino)methylene]pyrrolidine-2-carboxylates. The crystal and molecular structure of (Z)-isopropyl 2-hydroxy-4,5-dioxo-1-phenyl-3-[phenyl(phenylamino)methylene]pyrrolidine-2-carboxylate was proved by XRD analysis.
Toru Nagasawa - One of the best experts on this subject based on the ideXlab platform.
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Conversion of Pyrrole to Pyrrole‐2‐carboxylate by Cells of Bacillus megaterium in Supercritical CO2.
ChemInform, 2010Co-Authors: Tomoko Matsuda, Toru Nagasawa, Tadao Harada, Yoichi Ohashi, Reiko Yanagihara, Kaoru NakamuraAbstract:Pyrrole was converted to Pyrrole-2-Carboxylate in supercritical CO2 using cells of Bacillus megaterium PYR 2910, and the yield of the carboxylation reaction in supercritical CO2 was 12 times higher than that under atmospheric pressure.
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Biological Kolbe-Schmitt carboxylation: Possible use of enzymes for the direct carboxylation of organic substrates
Future Directions in Biocatalysis, 2007Co-Authors: Toyokazu Yoshida, Toru NagasawaAbstract:Abstract The occurrence of the enzymes catalyzing the Kolbe-Schmitt carboxylation has been shown, and the characterization of these enzymes has been reviewed. Among them, 2,6-dihydroxybenzoate decarboxylase and Pyrrole-2-Carboxylate decarboxylase efficiently catalyze the reverse carboxylation reaction and accumulate high concentration of 2,6-dihydroxybenzoate from 1,3-dihydroxybenzene and Pyrrole-2-Carboxylate from pyrrole, respectively, in the presence of 3M KHCO 3 . The possible application of biological Kolbe-Schmitt carboxylation has been discussed. Primary structure analysis of the decarboxylases suggests the latent distribution of various unidentified enzymes, probably catalyzing the regioselective carboxylation of aromatic and heterocyclic compounds, in microorganisms.
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Conversion of pyrrole to Pyrrole-2-Carboxylate by cells of Bacillus megaterium in supercritical CO2.
Chemical Communications, 2001Co-Authors: Tomoko Matsuda, Toru Nagasawa, Tadao Harada, Yoichi Ohashi, Reiko Yanagihara, Kaoru NakamuraAbstract:Pyrrole was converted to Pyrrole-2-Carboxylate in supercritical CO2 using cells of Bacillus megaterium PYR 2910, and the yield of the carboxylation reaction in supercritical CO2 was 12 times higher than that under atmospheric pressure.
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Carbon dioxide fixation by reversible Pyrrole-2-Carboxylate decarboxylase and its application
Journal of Molecular Catalysis B-enzymatic, 2001Co-Authors: Marco Wieser, Toyokazu Yoshida, Toru NagasawaAbstract:Inducible Pyrrole-2-Carboxylate decarboxylase from Bacillus megaterium PYR2910 catalyzes the decarboxylation of Pyrrole-2-Carboxylate to stoichiometric amounts of pyrrole and CO2. A unique feature of the homodimeric enzyme is its requirement for an organic acid such as acetate, propionate, butyrate or pimelate. A catalytic mechanism including a cofactor function of the organic acid was proposed. Due to an equilibrium constant of 0.3–0.4 M, the enzyme also catalyzes the reverse carboxylation of pyrrole after the addition of bicarbonate. For the synthesis of Pyrrole-2-Carboxylate, the reverse reaction was optimized and the equilibrium shifted towards the carboxylate. The product yield was 230 mM (25.5 g/l) Pyrrole-2-Carboxylate from 300 mM pyrrole in a batch reaction and 325 mM (36.1 g/l) from 400 mM pyrrole in a fed batch reaction, using both whole cells and the purified enzyme in a pH 8.0 reaction mixture with bicarbonate saturation of 1.9 M.
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Carbon dioxide fixation by reversible Pyrrole-2-Carboxylate decarboxylase from Bacillus megaterium PYR2910
FEBS Journal, 1998Co-Authors: Marco Wieser, Toyokazu Yoshida, Noriko Fujii, Toru NagasawaAbstract:: Pyrrole-2-Carboxylate decarboxylase from Bacillus megaterium PYR2910 attains a balanced reaction equilibrium with an equilibrium constant of 0.3-0.4 M. Therefore, the enzyme catalyzes the reverse carboxylation of pyrrole after addition of bicarbonate. For the synthesis of Pyrrole-2-Carboxylate, the reverse reaction was optimized and the equilibrium was shifted towards the carboxylate. The product yield was 230 mM (25.5 g/l) Pyrrole-2-Carboxylate from 300 mM pyrrole in a batch reaction and 325 mM (36.1 g/l) from 400 mM pyrrole in a fed-batch reaction, using both whole cells and the purified enzyme in a pH 8.0 reaction mixture with bicarbonate saturation of 1.9 M. Kinetic studies indicated, that bicarbonate is the reactive species used by this carbon dioxide-fixation enzyme.
Alexander F. Khlebnikov - One of the best experts on this subject based on the ideXlab platform.
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An isoxazole strategy for the synthesis of alkyl 5-amino-4-cyano-1H-Pyrrole-2-Carboxylates - versatile building blocks for assembling pyrrolo-fused heterocycles.
Organic & biomolecular chemistry, 2021Co-Authors: Anastasiya V. Agafonova, Liya D. Funt, Mikhail S. Novikov, Alexander F. KhlebnikovAbstract:A full atom-economical domino method has been developed for the preparation of alkyl 5-amino-4-cyano-1H-Pyrrole-2-Carboxylates by transannulation of 5-alkoxyisoxazoles with malononitrile under Fe(II) catalysis. Alkyl 5-amino-4-cyano-1H-Pyrrole-2-Carboxylates are excellent building blocks for various annulation reactions, leading to new derivatives of 1H-pyrrolo[1,2-a]imidazole and pyrrolo[2,3-d]pyrimidine. The DFT calculations of mechanistic details of alkyl 5-amino-4-cyano-1H-Pyrrole-2-Carboxylate formation are presented.
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an azirine strategy for the synthesis of alkyl 4 amino 5 trifluoromethyl 1h pyrrole 2 carboxylates
Synthesis, 2018Co-Authors: Liya D. Funt, Mikhail S. Novikov, Olesya A Tomashenko, Alexander F. KhlebnikovAbstract:1-(3,3,3-Trifluoro-2,2-dihydroxypropyl)pyridin-1-ium bromide serves as a trifluoromethyl-containing building block for the preparation of trifluoromethyl-substituted aminopyrroles based on the 2H-azirine ring expansion strategy. The primary products, 3-aryl-2-(methoxycarbonyl)-4-(pyridin-1-ium-1-yl)-5-(trifluoromethyl)pyrrol-1-ides, can be hydrogenated by H2/PtO2 to form alkyl 3-aryl-4-(piperidin-1-yl)-5-(trifluoromethyl)-1H-Pyrrole-2-Carboxylates and transformed into alkyl 4-amino-3-aryl-1-methyl-5-(trifluoromethyl)-1H-Pyrrole-2-Carboxylates via methylation/hydrazinolysis.
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4‐Diazo and 4‐(Triaz‐1‐en‐1‐yl)‐1H‐pyrrole‐2‐carboxylates as Agents Inducing Apoptosis
ChemistrySelect, 2017Co-Authors: Ekaterina E. Galenko, Mikhail S. Novikov, Alexander F. Khlebnikov, Alexey V. Galenko, Igor Kudryavtsev, Maxim A. Terpilowski, Maria K. Serebriakova, Andrey S. Trulioff, Nikolay V. GoncharovAbstract:New β-diazopyrrole and β-triazenylpyrrole derivatives were synthesized from isoxazoles and pyridinium salts in two and three steps, respectively. The apoptotic/necrotic difference for these compounds was estimated on THP-1 cell line. The most effective of the panel is methyl 3-diazo-2-(2,4-dimethylphenyl)-4-phenyl-3H-pyrrole-5-carboxylate which demonstrated cytotoxic activity from the lowest concentration of 3.3 μM with a steep rise of the apoptotic effect and the largest apoptotic/necrotic difference within the range of 3.3 to 33 μM. Moreover, this diazopyrrole showed the highest sum total of apoptotic and necrotic AUCs within the same low range of concentrations. Methyl 2-(4-bromophenyl)-3-diazo-4-(3-methoxyphenyl)-3H-pyrrole-5-carboxylate and methyl 5-(4-bromophenyl)-3-(3-methoxyphenyl)-4-(piperidin-1-yl/morpholin-4-yldiazenyl)-1H-Pyrrole-2-Carboxylates were found to be quite promising compounds which deserve further cytophysiological and mechanistic research using different cell lines.
