New developments in redox chemical delivery systems by means of 1,4-dihydroquinoline-based targetor: Application to galantamine delivery to the brain

New developments in redox chemical delivery systems by means of 1,4-dihydroquinoline-based targetor: Application to galantamine delivery to the brain.

Mihaela-Liliana Ţînţaş,^a, Lénaïg Foucout,^a Sylvain Petit,^a Sylvain Oudeyer,^a Fabienne Gourand,,^b,c,d Louisa Barré,^b,c,d Cyril Papamicaël,*^a Vincent Levacher,*^a

^a Normandie Univ, COBRA, UMR 6014 et FR 3038; Univ Rouen; INSA Rouen; CNRS, IRCOF, 1 rue Tesnière, 76821 Mont Saint Aignan cedex, France, Fax: [phone]; Tel: [phone]; E-mail: [e-mail]

^b CEA, DSV/I2BM, LDM-TEP Group, GIP Cyceron, Bd Henri Becquerel, BP 5229, 14074 Caen Cedex, France

^c Université de Caen Basse-Normandie, Caen, France

^d CNRS, UMR ISTCT 6301, LDM-TEP Group, GIP Cyceron, Caen, France


Supporting Material

General information

Chromatographic purification of compounds was achieved with Silica gel 60 (40-63 µm). Thin layer chromatographies were carried out on silica gel 60 F₂₅₄ (1.1 mm) with spot detection under UV light or phosphomolybdic acid or ninhydrin or KMnO₄ oxidation. ¹H NMR spectra were recorded at 300 MHz on a Bruker AVANCE 300 using CDCl₃, CD₃CN or DMSO-d₆ as solvents and with the residual solvent signals as internal standards unless otherwise indicated. Data appear in the following order: chemical shifts in ppm, multiplicity (s, singlet; d, doublet; t, triplet; q, quartet; m, multiplet; br, broaded), coupling constant J in Hz and number of protons. ¹³C NMR spectra were acquired at 75 MHz operating with broad band ¹H decoupling. IR spectra were obtained with Perkin Elmer Spectrum 100 FT-IR spectrometer or Perkin Elmer FT-IR 1650 spectrometer. The melting points of powder compounds were measured on a STUART-Advanced apparatus. Microanalyses were carried out at the analytical laboratory of our Department (IRCOF) on a Thermo Fisher FLASH 2000 series analyser found within ±0.4% of the theoretical values. High resolution mass spectra were performed by the Mass Spectrometry Laboratory of the University of Rouen on a Waters LCT Premiere ESI-TOF spectrometer. All solid phase chemistry was carried out on a Quest 210 Parallel Synthesizer from Argonaut. In vitro AChE inhibitory activities were measured by the Centre d’Etudes et de Recherche sur le Médicament de Normandie (CERMN).

¹H and ¹³C NMR spectra of compound 2_____________________________________________________2

¹H and ¹³C NMR spectra of compound 3a____________________________________________________3

¹H and ¹³C NMR spectra of compound 3b____________________________________________________4

¹H and ¹³C NMR spectra of compound 3c____________________________________________________5

¹H and ¹³C NMR spectra of compound 4a____________________________________________________6

¹H and ¹³C NMR spectra of compound 3d____________________________________________________7

¹H NMR spectrum of compound 4b_________________________________________________________8

¹H NMR spectrum of compound 3e_________________________________________________________8

¹H NMR spectrum of compound 5a_________________________________________________________9

IR spectrum of compound 6a______________________________________________________________10

¹³C NMR (gel) of compound 6a____________________________________________________________10

IR spectrum of compound 6b______________________________________________________________11

IR spectrum of compound 6c______________________________________________________________12

¹H and ¹³C NMR spectra of compound 3g____________________________________________________13

¹H and ¹³C NMR spectra of compound 4d____________________________________________________14

¹H and ¹³C NMR spectra of compound 7a____________________________________________________15

¹H and ¹³C NMR spectra of compound 7b____________________________________________________16

¹H and ¹³C NMR spectra of compound 7c____________________________________________________17

¹H and ¹³C NMR spectra of compound 4e____________________________________________________18

¹H and ¹³C NMR spectra of compound 5b____________________________________________________19