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Amides from Piper capense with CNS Activity – A Preliminary SAR Analysis
Department of Medicinal Chemistry, Faculty of Pharmaceutical Sciences, University of Copenhagen, Universitetsparken 2, DK-2100 Copenhagen, Denmark
Research Centre for Plant Growth and Development, School of Biological and Conservation Sciences, University of KwaZulu-Natal, Pietermaritzburg, Private Bag X01, Scottsville 3209, South Africa
* Author to whom correspondence should be addressed.
Received: 8 September 2009; in revised form: 25 September 2009 / Accepted: 25 September 2009 / Published: 25 September 2009
Abstract: Piper capense L.f. (Piperaceae) is used traditionally in South Africa as a sleep inducing remedy. Bioassay-guided fractionation of the roots of P. capense led to the isolation of piperine (1) and 4,5-dihydropiperine (2), which showed moderate affinity for the benzodiazepine site on the GABAA receptor (IC50 values of 1.2 mM and 1.0 mM, respectively). The present study suggests that strict structural properties of the amides are essential for affinity. Taken together, these observations suggest that the carbon chain must contain not less than four carbons, and that a conjugated double bond, adjacent to the amide group, is necessary for binding to the receptor and that the amine part should be bulky.
Keywords: Piper capense; piperine; GABA; benzodiazepine; epilepsy; multi target effect
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Pedersen, M.E.; Metzler, B.; Stafford, G.I.; Van Staden, J.; Jäger, A.K.; Rasmussen, H.B. Amides from Piper capense with CNS Activity – A Preliminary SAR Analysis. Molecules 2009, 14, 3833-3843.
Pedersen ME, Metzler B, Stafford GI, Van Staden J, Jäger AK, Rasmussen HB. Amides from Piper capense with CNS Activity – A Preliminary SAR Analysis. Molecules. 2009; 14(9):3833-3843.
Pedersen, Mikael E.; Metzler, Bjørn; Stafford, Gary I.; Van Staden, Johannes; Jäger, Anna K.; Rasmussen, Hasse B. 2009. "Amides from Piper capense with CNS Activity – A Preliminary SAR Analysis." Molecules 14, no. 9: 3833-3843.