58493-50-8Relevant academic research and scientific papers
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.
Lipophilicity of capsaicinoids and capsinoids influences the multiple activation process of rat TRPV1
Morita, Akihito,Iwasaki, Yusaku,Kobata, Kenji,Iida, Tohko,Higashi, Tomohiro,Oda, Kyoko,Suzuki, Asami,Narukawa, Masataka,Sasakuma, Shiho,Yokogoshi, Hidehiko,Yazawa, Susumu,Tominaga, Makoto,Watanabe, Tatsuo
, p. 2303 - 2310 (2007/10/03)
Analogs of capsaicin, such as capsaicinoids and capsinoids, activate a cation channel, transient receptor potential cation channel vanilloid subfamily 1 (TRPV1), and then increase the intracellular calcium concentration ([Ca2+]i). Th
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.
Vanilloids. 1. Analogs of Capsaicin with Antinociceptive and Antiinflammatory Activity
Janusz, John M.,Buckwalter, Brian L.,Young, Patricia A.,LaHann, Thomas R.,Farmer, Ralph W.,et al.
, p. 2595 - 2604 (2007/10/02)
As part of a program to establish structure-activity relationships for vanilloids, analogs of the pungent principle capsaicin, the alkyl chain portion the parent structure (and related compounds derived from homovanillic acid) was varied.In antinociceptive and antiinflammatory assays (rat and mouse hot plate and croton oil-inflamed mouse ear), compounds with widely varying alkyl chain structures were active.Short-chain compounds were active by systemic administration in the assays mentioned above but they retained the high pungency and acute toxicity characteristic of capsaicin.In contrast, the long chain cis-unsaturates, NE-19550 (vanillyloleamide) and NE-28345 (oleylhomovanillamide), were orally active, less pungent, and less acutely toxic than capsaicin.The potential of these compounds as antiinflammatory/analgesic agents is discussed in light of recent data on the mechanism of action of vanilloids on sensory nerve fibers.
