1193-62-0Relevant articles and documents
Nucleophilic and electrophilic cyclization of N-alkyne-substituted pyrrole derivatives: Synthesis of pyrrolopyrazinone, pyrrolotriazinone, and pyrrolooxazinone moieties
Yenice, I??l,Basceken, Sinan,Balci, Metin
, p. 825 - 834 (2017)
Intramolecular nucleophilic and electrophilic cyclization of N-alkyne-substituted pyrrole esters is described. Efficient routes towards the synthesis of pyrrolopyrazinone, pyrrolotriazinone and pyrrolooxazinone have been developed. First, N-alkyne-substituted pyrrole ester derivatives were synthesized. Introduction of various substituents into the alkyne functionality was accomplished by a copper-catalyzed cross-coupling reaction. Nucleophilic cyclization of N-alkyne-substituted methyl 1H-pyrrole-2-carboxylates with hydrazine afforded the 6-exo-dig/6-endo-dig cyclization products depending on the electronic nature of the substituents attached to the alkyne. On the other hand, cyclization of N-alkyne-substituted methyl 1H-pyrrole-2-carboxylates with iodine only resulted in the formation of the 6-endo-dig cyclization product regardless of the substitution of the alkyne functionality.
Isomeric chiral pyrrole diamides and their efficacy in enantioselective sensing of tartrate in sol–gel medium
Ghosh, Kumaresh,Majumdar, Anupam
, p. 3629 - 3634 (2016)
Pyridinium motif-based chiral pyrrole diamide clefts 1 and 2 have been designed and synthesized for chiral recognition of hydroxycarboxylates in sol–gel medium. Of the two isomeric chiral receptors, receptor 1 shows selective sensing of D-tetrabutylammonium tartrate over its mirror image isomer in CH3CN. The isomeric receptor 2 did not show any enantioselectivity in the recognition. Moreover, the receptor 1 validates prompt visual sensing of D-tartrate through gelation. The recognition properties of the receptors have been studied by fluorescence, UV–vis,1H NMR and CD spectroscopic methods.
Computer Modeling and Synthesis of Potential Inhibitors of Tyrosine Kinase BCR-ABL with the T315I Mutation
Fedarkevich, A. N.,Sharko, O. L.,Shmanai, V. V.
, p. 187 - 198 (2020)
Abstract—: A comparative analysis of the interaction of the chimeric protein BCR-ABL, of the normal type and with the T315I mutation, with known inhibitors as well as compounds potentially capable of inhibiting the mutant protein has been carried out by computer modeling. It has been shown that the compounds proposed are incorported into the structure of the protein with the retention of the basic hydrogen bonds and intermolecular interactions. Two structures containing the pyrrole cycle have been synthesized, which, according to the results of computer modeling, appear to be most promising.
Highly stable self-association of 5-(guanidiniocarbonyl)-1H-pyrrole- 2carboxylate in DMSO - The importance of electrostatic interactions
Schmuck, Carsten
, p. 2397 - 2403 (1999)
The zwitteriomc compound 5-(guanidiniocarbonyl)-1H-pyrrole-2-carboxylate (1) self-assembles to form dimers, which are completely stable in DMSO even at 170 °C or at concentrations of 0.001 mM. This high stability stems from a combination of multiple weak interactions. NMR titrations of 1H-pyrrole-2- carboxylate (5) with (1H-pyrrole-2-carbonyl)-guanidinium (6) and [5- (methoxycarbonyl)-1H-pyrrole-2-carbonyl]guanidinium (8) led to binding constants of K ? 106 mol-1 in DMSO and K ? 103 mol-1 in 40% water/DMSO for carboxylate binding by the 2-(guanidiniocarbonyl)pyrrole moiety. The stability constant for the dimer 12 in DMSO could therefore be estimated as K ? 1012 mol-1. In solution, the self-association process of 1 can be completely disrupted by protonation of the carboxylate group. In the solid state, however, the hydrochloride salt 1+ also exists as a similar but only very weakly hydrogen-bonded dimer.
Vanadate(v)-dependent bromoperoxidase immobilized on magnetic beads as reusable catalyst for oxidative bromination
Wischang, Diana,Hartung, Jens,Hahn, Thomas,Ulber, Roland,Stumpf, Tobias,Fecher-Trost, Claudia
, p. 102 - 108 (2011)
Vanadate(v)-dependent bromoperoxidase I (Ascophyllum nodosum) was immobilized on magnetic micrometre-sized particles in quantitative yields, with up to 40% retention of initial bromoperoxidase (BPO) activity. The immobilized enzyme was stable with a half-life time of about 160 days. It served as reusable catalyst for bromide oxidation with H2O2 in up to 14 consecutive experiments. Reactivity that resulted from enzymatic bromide oxidation was applicable for methyl pyrrole-2-carboxylate conversion into derivatives of naturally occurring compounds (e.g. from Agelas oroides) with product selectivity of up to 75%.
Studies on the organic fluorine compounds. XXIV. Photochemical trifluoromethylation of aromatic compounds
Kobayashi,Kumadaki,Ohsawa,et al.
, p. 1247 - 1249 (1978)
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Sonnet
, p. 97 (1972)
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