Amides from Piper capense with CNS activity: a preliminary SAR analysis
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Amides from Piper capense with CNS activity : a preliminary SAR analysis. / Pedersen, Mikael Egebjerg; Metzler, Bjørn; Stafford, Gary Ivan; van Staden, Johannes; Jäger, Anna Katharina; Rasmussen, Hasse Bonde.
In: Molecules, Vol. 14, No. 9, 2009, p. 3833-3843.Research output: Contribution to journal › Journal article › Research › peer-review
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TY - JOUR
T1 - Amides from Piper capense with CNS activity
T2 - a preliminary SAR analysis
AU - Pedersen, Mikael Egebjerg
AU - Metzler, Bjørn
AU - Stafford, Gary Ivan
AU - van Staden, Johannes
AU - Jäger, Anna Katharina
AU - Rasmussen, Hasse Bonde
N1 - Keywords: Piper capense; piperine; GABA; benzodiazepine; epilepsy; multi target effect
PY - 2009
Y1 - 2009
N2 - 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 GABA(A) receptor (IC(50) 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.
AB - 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 GABA(A) receptor (IC(50) 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.
KW - Former Faculty of Pharmaceutical Sciences
U2 - 10.3390/molecules14093833
DO - 10.3390/molecules14093833
M3 - Journal article
C2 - 19783959
VL - 14
SP - 3833
EP - 3843
JO - Molecules
JF - Molecules
SN - 1420-3049
IS - 9
ER -
ID: 14856700