L. Chromatographies-sur-couche-mince, M. , and A. Uv, CCM) ont été effectuées sur deux types de support, silice ou alumine

. Le-diméthylformamide, DMF) est dégazé par bullage d'argon, séché sur CaH 2 et distillé sous vide poussé à ~35 °C, puis conservé sous argon à l

L. Ganciclovir, 394 mg ; 1,54 mmol ; 1,000 éq.) est mis en suspension dans le DMF dégazé à l'argon et distillé sur CaH

. La-triéthylamine, mg ; 0,04 mmol ; 0,025 éq.) sont ajoutés, et le mélange sous agitation magnétique est chauffé à 40 °C sous argon. Le chlorure de p-anisyldiphénylméthane (1,020 g ; 3,30 mmol ; 2,100 éq.) est alors ajouté par portion, et le mélange devenant presque limpide prend une teinte orange-rouille. Au bout de 2,5 heures d'agitation sous argon à 40 °C, un contrôle CCM (SiO 2 ; DCM/MeOH 90:10) montre la formation de trois produits de polarité croissante, dont l'intermédiaire est majoritaire, Du MeOH (1 mL) est alors ajouté au milieu réactionnel avant d'évaporer le DMF sous vide poussé. Le résidu huileux repris dans le DCM (50 mL) est lavé par une solution saturée de NaHCO 3 et la phase organique est séchée sur Na

. Puis-filtrée-sur-coton, Après évaporation du filtrat, le solide brut obtenu est chromatographié sur gel de silice élué par un gradient DCM 100% => DCM/MeOH 90:10 pour donner 626 mg du ganciclovir désiré N(2)-O(3')-bis-tritylé (solide blanc

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. Conjugué-calixarène-mono-aciclovir-n-tritylé, 23-tétra-(tert-butyl)-25-[3, p.28

D. Meoh, Le synthon aciclovir 10 (440 mg ; 0,88 mmol ; 1,20 éq.) est alors ajouté au milieu, suivi par la 1,1,3,3-tétraméthylguanidine (0,64 mL15 mmol éq.) faisant apparaitre une légère coloration jaune. Après 15 heures dans ces conditions, le solvant est évaporé et le résidu huileux dissout dans le DCM (50 mL) est lavé par une solution aqueuse d'acide citrique 5% (50 mL), La phase organique est séchée par Na 2 SO 4 , filtrée sur coton et évaporée. Le résidu solide est chromatographié sur gel de silice élué par un gradient DCM 100% => DCM/MeOH 96:4 permet d'obtenir 151 mg du conjugué calixarène-aciclovir 20 (17%), p.0

. Le-solide-blanc-est-trituré-dans-le-n-pentane, mL), passé dans un bain à ultra-son et filtré sur RMN 1 H (400 MHz, DMSO-d 6 ) : 1,120 (s, 18 H, C(CH 3 ) 3 B) A), pp.149-167

A. and J. Hz, 668 (s, 6 H, NHC(Ph) 2 (PhOCH 3 )), OCH 2 CH 2 CH 2 OCO), pp.330058422-4815016634822836128

. Conjugué-calixarène-mono-aciclovir, 23-tétra-(tert-butyl)-25-[3-[(5'-O-aciclovir)- oxycarbonyl]-propoxy]-26, p.28

N. Aroh, 5 (? as (CH 3 ) : tertbutyl )(C=O) : carbodiester) ; large 1634,0 (Amide I et II + ?(C=O): amide Guanine + CF 3 (C=O)O), ) : Alkyl-O), pp.170-175

. Ar, CH 3 ) 3 C) (C(CH 3 ) 3 A), Ar(A)CH 2 Ar, p.195

C. Les-composés, mCX1 ont été synthétisés selon les procédures mises au point par Maxime Mourer, sans modifications particulières

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A. Casnati, F. Sansone, and R. Et-ungaro, Peptido- and Glycocalixarenes:?? Playing with Hydrogen Bonds around Hydrophobic Cavities, Accounts of Chemical Research, vol.36, issue.4, pp.246-254, 2003.
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A. E. Motornaya, L. M. Alimbarova, E. A. Shokova, and V. V. Et-kovalev, Synthesis and antiherpetic activity of N-(3-amino-1-adamantyl)calix[4]arenes, Pharmaceutical Chemistry Journal, vol.33, issue.7, pp.68-72, 2006.
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C. Geraci, G. M. Consoli, E. Galante, E. Bousquet, M. Pappalardo et al., CS Immunoadjuvant: Synthesis, Characterization, and Anticancer Immunological Evaluation, Bioconjugate Chemistry, vol.19, issue.3, pp.751-758, 2008.
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G. M. Consoli, G. Granata, D. Garozzo, T. Mecca, and C. Et-geraci, Self-assembly of a nucleotide-calixarene hybrid in a triangular supramolecule, Tetrahedron Letters, vol.48, issue.45, pp.7974-7977, 2007.
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G. M. Consoli, G. Granata, E. Galante, I. Di-silvestro, L. Salafia et al., Synthesis of water-soluble nucleotide-calixarene conjugates and preliminary investigation of their in vitro DNA replication inhibitory activity, Tetrahedron, vol.63, issue.44, pp.10758-10763, 2007.
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S. J. Harris, D. Coveney, and B. Et-costello, Anti-viral compounds Preparation of alkylated pyrogallol calixarene type compounds as anti-viral compounds, WO 02/44121, 2002.

A. W. Coleman, L. G. Baggetto, A. N. Lazar, M. H. Michaud, and S. Et-magnard, Derivatives of calixarenes as anticancer agent, 2003.

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I. I. Stoikov, S. A. Repejkov, I. S. Antipin, and A. I. Et-konovalov, Lipophilic aminophosphonates and their calix[4]arene derivatives: synthesis and membrane transport of biorelevant species, Heteroatom Chemistry, vol.126, issue.146, pp.518-527, 2000.
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S. A. Fernandes, L. F. Cabeca, A. J. Marsaioli, and E. Et-paula, Investigation of tetracaine complexation with beta-cyclodextrins and p-sulphonic acid calix[6]arenes by nOe and PGSE NMR, Journal of Inclusion Phenomena and Macrocyclic Chemistry, vol.162, issue.1???2, pp.395-401, 2007.
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L. Nault, A. Cumbo, R. F. Pretot, M. A. Sciotti, and P. Et-shahgaldian, Cell transfection using layer-by-layer (LbL) coated calixarene-based solid lipid nanoparticles (SLNs), Chemical Communications, vol.9, issue.30, pp.5581-5583, 2010.
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Y. Wang, D. Xin, K. Liu, M. Zhu, and . Xiang, Heparin???Paclitaxel Conjugates as Drug Delivery System: Synthesis, Self-Assembly Property, Drug Release, and Antitumor Activity, Bioconjugate Chemistry, vol.20, issue.12, pp.2214-2221, 2009.
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K. Vemula-praveen, A. Gregory, M. Karp-jeffrey, and G. Et-john, Self-assembled prodrugs: An enzymatically triggered drug-delivery platform, Biomaterials, vol.30, issue.3, pp.383-393, 2009.
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F. Sansone, M. Segura, and R. Et-ungaro, Calixarenes in Bioorganic and Biomimetic Chemistry, Calixarenes, pp.496-512, 2001.

R. Zadmard and T. Et-schrader, Amino-Acid, Peptide and Protein Sensing. Calixarenes in Monolayers, Calixarenes in the Nanoworld, pp.287-309, 2007.
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D. M. Rudkevich, Self-Assembly in Solution, pp.155-180, 2001.
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V. Böhmer and A. Et-shivanyuk, CALIXARENES IN SELF-ASSEMBLY PHENOMENA, pp.203-240, 2000.
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W. Sliwa and C. Et-kozlowski, Part III: Supramolecular Calixarene Structures and Related Systems, pp.181-256, 2009.

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