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

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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: +33 2 355 224 69; Tel: +33 2 355 224 85; E-mail: Vincent.levacher@insa-rouen.fr

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





































































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