Solid-phase synthesis of quinol fatty alcohols, design of N/O-substituted quinol fatty alcohols and comparative activities on axonal growth.
Following the promising activity of Q2FA15 on axonal growth, two new series of N/O-substituted QFAs were synthesized, based on a SN2-type reaction. O-alkylated QFA bearing 14 carbon atoms on the side chain (n=14) shows a very potent activity on axonal growth though lowered when compared to Q2FA15. While O-alkylation allows good retention of the biological activity, N-alkylation abolishes it nonetheless. A solid-phase-supported synthesis of Q2FA15 allowing the conception of new hybrid compounds is also described.
Hanbali
Mazen
M
Laboratoire de Chimie Organique des Substances Naturelles, LC3-UMR7177 CNRS-ULP, Université Louis Pasteur, 67084 Strasbourg Cedex, France.
Bagnard
Dominique
D
Luu
Bang
B
D000818:Animals; D001369:Axons / Q000187:drug effects*; D005233:Fatty Alcohols / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D006873:Hydroquinones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D051379:Mice
D005233:Fatty Alcohols; D006873:Hydroquinones