Preparation,anticholinesterase activity and molecular docking of new lupane derivatives |
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| Institution: | 1. INQUISUR-CONICET, Departamento de Química, Universidad Nacional del Sur, Av. Alem 1253, B8000CPB Bahía Blanca, Argentina;2. UMYMFOR (CONICET-UBA), Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Ciudad Universitaria, Pabellón 2, 1428 Buenos Aires, Argentina;3. Instituto Universitario de Bio-Orgánica (CIBICAN), Av. Astrofísico Francisco Sánchez 2, 38206, Departamento de Química Orgánica, Universidad de La Laguna, Tenerife, Spain;1. IIB-INTECH (sede Chascomús) – UNSAM-CONICET. Intendente Marino Km 8,2. CC 164, 7130 Chascomús, Buenos Aires, Argentina;2. CIHIDECAR – CONICET, Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pabellón 2, 3p, Ciudad Universitaria, 1428 Buenos Aires, Argentina;1. Université de Toulouse; UPS; UMR 152 Pharma-Dev; Université Toulouse 3, Faculté des Sciences Pharmaceutiques, F-31062 Toulouse cedex 09, France;2. Institut de Recherche pour le Développement (IRD); UMR 152 Pharma-Dev; F-31062 Toulouse cedex 09, France;3. LAAS-CNRS, 7 avenue du Colonel Roche, F-31077 Toulouse cedex 4, France |
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| Abstract: | A set of twenty one lupane derivatives (2–22) was prepared from the natural triterpenoid calenduladiol (1) by transformations on the hydroxyl groups at C-3 and C-16, and also on the isopropenyl moiety. The derivatives were tested for their inhibitory activity against acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) and some structure–activity relationships were outlined with the aid of enzyme kinetic studies and docking modelization. The most active compound resulted to be 3,16,30-trioxolup-20(29)-ene (22), with an IC50 value of 21.5 μM for butyrylcholinesterase, which revealed a selective inhibitor profile towards this enzyme. |
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| Keywords: | Alzheimer’s disease Cholinesterase inhibitors Lupane derivatives Triterpenoids Molecular modeling |
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