153750-09-5Relevant articles and documents
Structure-activity relationships of the ultrapotent vanilloid resiniferatoxin (RTX): The side chain benzylic methylene
Appendino, Giovanni,Ech-Chahad, Abdellah,Minassi, Alberto,De Petrocellis, Luciano,Marzo, Vincenzo Di
scheme or table, p. 97 - 99 (2010/04/06)
The side chain benzylic methylene is a critical element for the vanilloid activity of resiniferatoxin (2a, RTX), and introduction of branching, oxygen functions, or isosteric substitution at this center proved detrimental, with a decrease of potency of 2-3 orders of magnitude compared to the natural product. Conversely, only a modest erosion of activity was observed upon α-methylation and α-methylenation of the side chain. Surprisingly, introduction of an iodine atom in the guaiacyl moiety of the oxygen isoster 2h led to an unexpected and remarkable (>1000-fold) increase of potency, affording 2i, a compound that outperforms RTX in terms of vanilloid agonism and represents the first one-digit picomolar ligand of a TRP channel discovered to date.
Phenyl alpha acyloxyalkanoic acids, derivatives and their therapeutic use
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, (2008/06/13)
Therapeutic as well as preventative measures to improve the cosmetic conditions or to alleviate the symptoms of dermatologic disorders with phenyl alpha acyloxyalkanoic acids and derivatives is disclosed. The cosmetic conditions and dermatologic disorders