Nouvelle synthèse de dérivés hétérocycliques thiazoliques, sélénazoliques, coumariniques, thiocoumariniques et quinolonéiques. Étude et évaluation de leur activité potentielle anticancéreuse

Abstract : We performed the synthesis of thiazoles, selenazoles, thieno[2,3-d]thiazoles and thieno[2,3-d][1,3] selenazoles which are easily prepared from cyanamide and carbon disulfide. By this way, we have synthesized 4-amino-1,3-thiazoles et 1,3-selenazoles substituted in position 2 and 5 in two steps. Used these heterocycles, 4-halogeno-1,3-thiazoles et 1,3-selenazoles were synthesized by Doyle’s method. Lability of halogens in previous derivatives allowed to prepare new thieno[2,3-d]thiazoles and [1,3]selenazoles. Determination of the antiproliferative activity of these compounds has brought out two compounds, showing IC50 values in micromolar range on investigated cancer cell lines: MCF-7, PC-3, Hs683, U373, SKMEL-28, and A549. One particular compound showed a high activity of anti-Na+/K+-ATPase and anti-ROS. In addition in the second subject, we were interested in the development of the synthesis of two isomers (alpha and beta) of 4-butoxylvinyl-coumarins, -thiocoumarin and -2-quinolones by Heck coupling. We showed that, depending on the substituent in the position 4 of the heterocycle, the coupling was regioselective. These butoxyvinylic derivatives, characterized by dienic character, were studied for their reactivity, stereoselectivity and regioselectivity with several dienophiles in Diels-Alder cycloaddition. Among all the polyheterocyclic compounds prepared, we have identified the tetracyclic compounds with quinonic ring which have potential anticancer activity by inhibition of CDC25 phosphatase and on several tumor cell lines
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Zhanjie Xu. Nouvelle synthèse de dérivés hétérocycliques thiazoliques, sélénazoliques, coumariniques, thiocoumariniques et quinolonéiques. Étude et évaluation de leur activité potentielle anticancéreuse. Autre. Université de Lorraine, 2014. Français. ⟨NNT : 2014LORR0079⟩. ⟨tel-01750802⟩

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