65939-65-3Relevant academic research and scientific papers
Aryl and ethoxycarbonyl derivatives of pyrroles, 2H pyrroles and 3,4-dihydropyrroles and their immunoactivity of human T lymphocytes
Birouk,Harraga,Panouse-Perrin,Robert,Damelincourt,Theobald,Mercier,Panouse
, p. 91 - 99 (2007/10/02)
Several pyrroles, 2H pyrroles, 3,3-dihydropyrroles substituted in various positions with phenyl and ethoxycarbonyl groups, were prepared in order to study in vitro their immunoactivity on human T lymphocytes. The best action was observed when on the pyrrole cycle, a carboxylic chain in position 2, an aromatic cycle in 5, and a substituent in 3, particularly a phenyl or a carboxylic ester were simultaneously found to exist. A conformational approach, performed by magnetic anisotropy quantification of phenyls, using Johnson and Bovey increments, showed that the orthogonality of the substituent in 3 is important as regards the pyrrolic cycle. Thus, the ethyl 3,5-diphenylpyrrole-2-carboxylate ester 8 appears to be the most interesting as it is more efficient than the levamisole chlorhydrate in the tests connected with the lymphoblastic transformation in presence of PHA (phyto-hemagglutinin) and related to the mobilisation of CD2 receptors.
The Synthesis and Chemistry of Azolenines. Part 4. Preparation and Rearrangement of some 3,5-Diaryl-2H-pyrrole-2,2-dicarboxylic Esters
Sammes, Michael P.,Chung, Margaret W. L.,Katritzky, Alan R.
, p. 1773 - 1780 (2007/10/02)
Oxidation of diethyl 3,5-diaryl-3,4-dihydro-2H-pyrrole-2,2-dicarboxylates (3) with chloranil in refluxing xylene gives not the 3,5-diaryl-2H-pyrrole-2,2-dicarboxylates (4) as reported by an earlier group, but instead the rearranged, isomeric, 1H-pyrrole-1,2-dicarboxylates (5). 2H-Pyrroles (4) may be obtained from the dihydropyrroles (3) using DDQ in benzene at room temperature; they rearrange to the isomers (5) in boiling xylene via an acyl -sigmatropic shift from carbon to nitrogen, a novel process in the 2H-pyrrole series.Thermal analyses indicate that the rearrangement is concerted with negligible charge separation in the transition state.Other novel 3,5-diaryl-1H-pyrrole-2-carboxylic acid derivatives are described.
