58493-50-8Relevant articles and documents
Highly efficient synthesis of capsaicin analogues by condensation of vanillylamine and acyl chlorides in a biphase H2O/CHCl3 system
Wang, Bo,Yang, Fan,Shan, Yi-Fan,Qiu, Wen-Wei,Tang, Jie
supporting information; experimental part, p. 5409 - 5412 (2009/10/17)
Highly efficient synthesis of capsaicin analogues was developed using condensation of vanillylamine with acyl chlorides in a biphase H2O/CHCl3 system under mild conditions. For C4-C18 aliphatic or aromatic acyl chlorides, the yields were up to 93-96% with high purity after a simple work-up procedure, and only 1-1.16 equiv of acyl chloride was needed in the reaction.
N-acylvanillamides: Development of an expeditious synthesis and discovery of new acyl templates for powerful activation of the vanilloid receptor
Appendino, Giovanni,Minassi, Alberto,Morello, Aniello Schiano,De Petrocellis, Luciano,Di Marzo, Vincenzo
, p. 3739 - 3745 (2007/10/03)
A simple and general synthesis of vanillamides was developed and employed to screen acids from the fatty and isoprenoid pools for new acyl templates of biological relevance as capsaicin analogues. Potent activation of the human vanilloid receptor 1 (VR1) was observed for the vanillamides of certain polyfunctional acids from both pools, showing that the vanilloid activity of capsaicinoids can be substantially improved by introducing polar groups and/or unsaturations on the acyl moiety. The activity of the unsaturated analogues was maintained or even increased by cyclopropanation, while ω dimerization led to a substantial increase of activity. Because of the wide structural diversity of the library of compounds screened, these observations could not be translated into a single framework of structure-activity relationships. Nevertheless, a series of new highly active leads was identified, validating the pharmacological potential of the unnatural combination of natural building blocks to provide new bioactive compounds.
