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Bioorg Med Chem. 2014 Jul 1;22(13):3341-50. doi: 10.1016/j.bmc.2014.04.050. Epub 2014 May 5.

Preparation, anticholinesterase activity and molecular docking of new lupane derivatives.

Author information

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.
4
INQUISUR-CONICET, Departamento de Química, Universidad Nacional del Sur, Av. Alem 1253, B8000CPB Bahía Blanca, Argentina. Electronic address: apmurray@uns.edu.ar.

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 21.5μM for butyrylcholinesterase, which revealed a selective inhibitor profile towards this enzyme.

KEYWORDS:

Alzheimer’s disease; Cholinesterase inhibitors; Lupane derivatives; Molecular modeling; Triterpenoids

PMID:
24835788
DOI:
10.1016/j.bmc.2014.04.050
[Indexed for MEDLINE]

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