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SYNTHESE DE NOUVELLES QUINONES HETEROCYCLIQUES PAR APPLICATION DES REACTIONS DE CYCLOADDITIONS DE DIELS-ALDER ET 1,3-DIPOLAIRE. EVALUATION IN VITRO DE LEUR ACTIVITE SUR TOXOPLASMA GONDII

Abstract : Toxoplasmosis is an ubiquitous anthropozoonosis induced by Toxoplasma gondii. Despite of several researchs, the whole stock of drugs remain restricted. The aim of the works in this report is the synthesis of carbazolequinones and valuation of efficacy against T. gondii. Natural carbazolequinones like Calothrixines exhibit antiparasitic et cytoxotoxic properties. The para- and ortho-quinones like benzo-, isoxazolo- and triazolo-carbazolequinones synthesis was investigate by regioselective [4+2] or 1,3-dipolar cycloaddition. The strategy of synthesis from monobromide dipolarophile can in fact have an access to required regioisomer with selectivity. Proofs of regiochemistry was made by NMR 1H NOE and study of correlation by 1H-13C HMBC. Concerning biological assessment, compounds inhibit the growth of T. gondii like sulfadiazine and pyrimethamine with cytotoxicity against myelomonocytic THP1 cells. Any synthesised compounds inhibit PNP, key enzyme of purine salvage pathway, unique way for the parasit to have access to puric basis. The inhibition of growth of T. gondii by our compounds isn't due to inhibition of PNP.
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https://tel.archives-ouvertes.fr/tel-00281991
Contributor : Muriel Compain-Batissou Cudel <>
Submitted on : Wednesday, May 28, 2008 - 6:27:38 PM
Last modification on : Monday, October 19, 2020 - 10:53:14 AM
Long-term archiving on: : Friday, May 28, 2010 - 8:08:14 PM

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Muriel Compain-Batissou Cudel. SYNTHESE DE NOUVELLES QUINONES HETEROCYCLIQUES PAR APPLICATION DES REACTIONS DE CYCLOADDITIONS DE DIELS-ALDER ET 1,3-DIPOLAIRE. EVALUATION IN VITRO DE LEUR ACTIVITE SUR TOXOPLASMA GONDII. Chimie. Université Claude Bernard - Lyon I, 2007. Français. ⟨tel-00281991⟩

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