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Synthese Et Evaluation Biologique De Derives De L'aminobenzosuberone

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Synthese Et Evaluation Biologique De Derives De L'aminobenzosuberone Synthese et evaluation biologique de derives de l'aminobenzosuberone, inhibiteurs puissants et selectifs de l'aminopeptidase N ou CD13 Sarah Alavi To cite this version: Sarah Alavi. Synthese et evaluation biologique de derives de l'aminobenzosuberone, inhibiteurs puissants et selectifs de l'aminopeptidase N ou CD13. Chimie organique. Universit´ede Haute Alsace - Mulhouse, 2013. Fran¸cais. <NNT : 2013MULH4071>. <tel-01223670> HAL Id: tel-01223670 https://tel.archives-ouvertes.fr/tel-01223670 Submitted on 3 Nov 2015 HAL is a multi-disciplinary open access L'archive ouverte pluridisciplinaire HAL, est archive for the deposit and dissemination of sci- destin´eeau d´ep^otet `ala diffusion de documents entific research documents, whether they are pub- scientifiques de niveau recherche, publi´esou non, lished or not. The documents may come from ´emanant des ´etablissements d'enseignement et de teaching and research institutions in France or recherche fran¸caisou ´etrangers,des laboratoires abroad, or from public or private research centers. publics ou priv´es. THESE En vue de l’obtention du Présentée et soutenue Doctorat de l’Université de Haute-Alsace par : Sarah ALAVI Spécialité : Chimie Organique Le jeudi 28 novembre 2013 Synthèse et évaluation biologique de dérivés de l’amino-benzosubérone, inhibiteurs puissants et sélectifs de l’Aminopeptidase N ou CD13. Ecole Doctorale : Jean Henri-Lambert 494 – Pôle Chimie, Physique et Matériaux Unité de recherche : Laboratoire de Chimie Organique et Bioorganique (COB) – EA 4566 Directeurs de Thèse : Pr Céline TARNUS (COB – UHA Mulhouse) Dr Philippe BISSERET (COB – UdS Strasbourg) Rapporteurs : Dr Jean-Bernard BEHR (ICMR – Univ. Champagne-Ardenne Reims) Dr Siden TOP (Lab. Charles Friedel – ENSCP Paris) Examinateur : Pr Christine GERARDIN (LERMaB – UL Nancy) A la mémoire d’Adham Pirnia, A mes parents, Et à tous ceux qui me sont chers … AVANT-PROPOS Cette thèse a été réalisée au sein du Laboratoire COB dirigé par le Pr Céline Tarnus, tout d’abord à l’ENSCMu (de novembre 2009 à mai 2011) puis à l’Institut Jean-Baptiste Donnet (depuis juin 2011). Elle a été codirigée par le Pr Céline Tarnus et le Dr Philippe Bisseret, chargé de recherche CNRS. La Fondation pour l’ENSCMu, l’Université de Haute-Alsace et le laboratoire COB ont assuré le soutien financier de mes travaux de thèse. Dans le cadre de la Chaire ACTELION, j’ai eu l’opportunité de faire un stage d’échange international de 2 mois à la Faculté des Sciences Pharmaceutiques et Biomédicales de l’Université de Nagasaki sous la direction du Pr Masakasu Tanaka. 7 8 REMERCIEMENTS Effectuer une thèse est, pour beaucoup de mes confrères, un projet de recherche réalisé sur une période déterminée... Ma définition de la thèse est beaucoup plus personnelle et au travers de ce chapitre intitulé « Remerciements », j’en présenterai quelques alinéas. Mes premiers remerciements s’adressent tout naturellement au Pr Céline Tarnus, ma directrice de thèse qui au-delà des très bonnes relations professionnelles que nous avons entretenues, a su me faire confiance dès mon premier jour. Bien que très occupée par ses instances, elle a toujours su m’accueillir dans son bureau comme à son domicile pour répondre à mes innombrables questions. J’exprime également toute ma gratitude à Philippe Bisseret. Je ne mesure toujours pas la chance que j’ai eue de l’avoir en tant que directeur de thèse. Je suis très admirative de son savoir aussi bien en chimie que dans la vie de tous les jours en passant par l’art « cactéen ». Je remercie également les membres de ce jury, à savoir le Dr Jean-Bernard Behr, le Dr Siden Top et le Pr Christine Gerardin, pour l’intérêt qu’ils ont bien voulu porter à ce travail et d’avoir accepté d’honorer le jury de leur présence. A présent je me tourne auprès de tous ceux qui ont collaboré avec moi, de près comme de loin, tout au long de ma thèse. Tout d’abord, Didier, je te suis extrêmement reconnaissante pour toutes les heures que tu as consacrées à m’aider dans mes travaux de thèse. Ta détermination et ton génie en matière d’analyse spectroscopique sont exemplaires. Sans avoir fait le tour des labos du monde entier, je suis certaine que tu es le meilleur et inégalable. Cécile, depuis le déménagement du laboratoire, que tu as orchestré d’une main de maître, nos relations n’en sont que meilleures. Tout comme Didier, et bien que ton emploi du temps soit plus restreint, tu as toujours pris le temps de répondre à mes questions avec la pointe de fermeté qu’on te connaît. Albert, même si de votre temps, toutes les réactions marchaient et que depuis rien ne va plus, je vous assure que j’ai fait de mon mieux pour suivre tous les conseils que vous 9 avez eu la gentillesse de me prodiguer et ce, même une fois que vous aviez pris votre retraite. J’ai hâte de vous revoir pour converser (tant bien que mal) en allemand. Manu, ou devrais-je dire PerManuTor, tu as été d’une grande patience avec moi, et surtout à mes débuts. Fabienne, nos bonnes relations étaient bien souvent extra professionnelles, et c’est tant mieux, il n’y a pas que la Science dans la vie… Marjorie, je ne sais plus si tu étudies la tribologie des bactéries ou le clonage des matériaux mais une chose est sûre, tu le fais avec brio ! Aline, je pense que même plusieurs jours après mon départ, je rêverais de bons de commande et d’ordres de mission, mais je me souviendrais surtout de ta gentillesse avec, parfois, un grain de malice. Sébastien, ou l’homme le plus jeune au monde connaissant le plus de choses, je ne sais pas si c’est ta grande taille ou ta grande envie de tout savoir qui fait de toi un scientifique exceptionnel, mais je ne doute pas un instant que tu feras (et fais déjà) de brillantes choses. Bien que je n’aie pas effectué ma thèse dans l’université la plus prestigieuse au monde, il est indéniable que mes collègues du COB sont extraordinaires. J’ai réellement eu une chance inouïe d’être dans une équipe regorgeant de scientifiques tous plus épatants les uns que les autres. Si Mulhouse se situait près de la mer ou proche de domaines skiables, notre université serait certainement au Top10 du classement mondial ! En effet, Nicolas, même si je n’ai pas étroitement travaillé avec toi, il est certain que tu es un emblème de l’excellence en chimie, ici… et ailleurs. Tu t’es d’ailleurs entouré de gens qui seront sûrement, un jour, à ta hauteur : Cédric, qui d’une certaine manière est déjà un Grand homme, Stéphane, le « djeuns zarb », Anne-K, une mycolactone pas comme les autres, Morgan, le « réparator d’évaporator rotatif » (et que je remercie au passage tout particulièrement pour les nombreuses fois où il m’a aidée), Théo, mon fournisseur officiel de plantes vertes et de précieux conseils, et enfin Samir, mon compagnon de thèse avec qui nous avons partagé une belle aventure au Japon. Durant ma thèse, j’ai non seulement eu l’opportunité de faire de l’enseignement mais aussi de mieux connaître des chercheurs qui sont également des pédagogues et ont bien d’autres cordes à leur arc. Un grand merci à Delphine, Samuel, Hélène, Anna, le Pr Serge Neunlist, Vice-Président de l’UHA, et le Pr Pierre Llopiz, directeur de l’ENSCMu pour m’avoir acceptée comme l’une des vôtres durant l’année 2012-2013. Après avoir été votre étudiante (préférée, je n’en doute pas !) durant les 8 années (voire plus) à l’UHA, je suis passée de votre côté et j’ai continué à apprendre à vos côtés. 10 Je ne peux évidemment pas oublier de remercier ceux qui étaient là quand je suis arrivée et qui sont devenus aujourd’hui de grands et vrais Docteurs ! Lionel, ton amitié compte beaucoup pour moi, et, je te remercie d’avoir supporté mes milliards de « désolée » et « Sarades ». Emel, nos voyages sont sans doute les meilleurs souvenirs que j’ai de nous. A quand notre périple sur la route de l’Orient Express ? Céline, j’ai failli parler de tes belles jambes… dire que tu es une femme formidable me semble plus approprié. Mira, ton élégance est à la hauteur de ta générosité de cœur et de tes irrésistibles petits gâteaux libanais. Et Hamid, j’ai envie de dire « Tout pareil » pour te dire merci. Je tiens aussi à remercier tout particulièrement mes collègues de fin de thèse. Ma chère VeryNice, je pense être ta plus grande fan, et à juste titre : tu es géniale ! Ton équipe à une chance inouïe de t’avoir et je suis certaine que tu es promise à un bel avenir. Bryce, ta bonne humeur et ton petit brin de folie font de toi un super collègue, ne change pas. Thomas, je ne connais pas de personne plus dévouée et serviable que toi. Je te remercie pour tout ce que tu as fait et feras pour moi, car je sais que je pourrais toujours compter sur toi. Germain, il serait de bon aloi que je t’adresse toute ma profonde gratitude et « remercititude » pour toute l’aide et le soutien que tu m’as généreusement apportés. Tu n’as jamais compté les heures pour m’aider et sans toi, il est certain que je n’y serai pas arrivée. Et ma chère Aurély… ma chère collègue de galère. Je ne sais pas si ce sont tes beaux yeux noisette à la pointe de miel, ou toutes les émotions que nous avons eues ensemble que je retiendrai.
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