- N-SUBSTITUTED 3,4-BIS (CATECHOL) PYRROLE COMPOUNDS, AND THE PREPARATION AND USE THEREOF IN THE TREATMENT OF CANCER
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The present invention relates to a compound of formula (I) in which: —m is an integer from 0 to 3, preferably from 0 to 2; n is an integer from 0 to 3, preferably from 0 to 2; m+n≧1; EAG is an electro-attractive group chosen independently from among a halogen atom, an NO2, CF3, CCI3, CN, CO2H, (C═O)NR2, CH═NR, (C═S)OR, (C═O)SR, CS2R, SO2R, SO2NR2, SO3R, P(O)(OR)2, P(O)(R)2, B(OR)2 group where R is a (C1-C6) alkyl radical, a phenyl group or a hydrogen atom; A is a saturated or unsaturated, linear or branched hydrocarbon chain including 1 to 10 atoms of carbon; and R1 and R2 each represent independently from one another a hydrogen atom, a CO-(Ci-C6)-alkyl, (C1-C6) alkyl, phenyl or phenyl-(C1-C6)-alkyl group, in which R1 and R2 form, together with the nitrogen atom they carry, a 5- to 15-member heterocycle, optionally substituted by a (C1-C6) alkyl group; including its stereoisomers and the mixtures thereof, or a pharmaceutically acceptable salt of same.
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Paragraph 0050; 0051
(2015/12/26)
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- A concise formation of N-substituted 3,4-diarylpyrroles-synthesis and cytotoxic activity
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A short synthesis of N-substituted 3,4-diarylpyrroles by condensation of a phenacyl halide with a primary amine and a phenylacetaldehyde is reported. The key step is an intramolecular cyclization of an in situ generated enamine onto a ketone. Using differently substituted aromatic reactants and N-(3-aminopropyl)azatricyclodecane as the amine component, the preparation of analogs of the cytotoxic marine alkaloid halitulin could be achieved. The cytotoxicity of some of the compounds obtained by this method was studied, and one of them proved to be a very potent derivative, acting at a nanomolar concentration, in a caspase-independent cell death mechanism.
- Egorov, Maxim,Delpech, Bernard,Aubert, Genevieve,Cresteil, Thierry,Garcia-Alvarez, Maria Concepcion,Collin, Pascal,Marazano, Christian
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p. 1518 - 1524
(2014/03/21)
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