23512-46-1Relevant articles and documents
Synthesis of piperamides and new analogues from natural safrole
De Araújo Jr., Jo?o X.,Barreiro, Eliezer J.,Parente, José P.,Fraga, Carlos A. M.
, p. 263 - 273 (1999)
Species of the Piper genus are amply known for their biological activities. This paper describes a new synthetic route for the preparation of piperamides and analogues, using as an efficient precursor, the Brazilian natural product safrole (1). The amides (6a-c) were obtained in 25-32% overall yield.
Amides from Piper capense with CNS activity - A preliminary SAR analysis
Pedersen, Mikael E.,Metzler, Bjorn,Stafford, Gary I.,Van Staden, Johannes,Jaeger, Anna K.,Rasmussen, Hasse B.
experimental part, p. 3833 - 3843 (2009/12/26)
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.
Three-component synthesis of (E)-α,β-unsaturated amides of the piperine family
Schobert,Siegfried,Gordon
, p. 2393 - 2397 (2007/10/03)
Selective formation of (E)-α,β-unsaturated amides by intermolecular three-component reaction between aldehydes, amines (1° or 2°) and ketenylidenetriphenylphosphorane (Ph3P=C=C=O) is described. Natural amides such as fagaramide and piperines could be prepared from immediately available educts. The method is shown to be extendable to the preparation of thioesters from thiols and aldehydes.
