89942-36-9Relevant articles and documents
Electronic control of product distribution in the [5+5]-coupling of ortho-alkynylbenzaldehyde derivatives and γ,δ-unsaturated carbene complexes
Camacho-Davila, Alejandro,Gamage, Lalith S.R.,Wang, Zhipeng,Herndon, James W.
supporting information; scheme or table, p. 4954 - 4960 (2010/08/19)
The coupling of highly oxygenated ortho-alkynylbenzaldehyde derivatives with γ,δ-carbene complexes was evaluated systematically. In all of the electron-rich systems investigated the exclusive product of the reaction is the dihydrophenanthrene derivative.
The taming of capsaicin. Reversal of the vanilloid activity of N-acylvanillamines by aromatic iodination
Appendino, Giovanni,Daddario, Nives,Minassi, Alberto,Moriello, Aniello Schiano,De Petrocellis, Luciano,Di Marzo, Vincenzo
, p. 4663 - 4669 (2007/10/03)
Aromatic iodination ortho to the phenolic hydroxyl reverts the activity of the ultrapotent vanilloid agonist resiniferatoxin (RTX, 1a), generating the ultrapotent antagonist 5′-iodoRTX (1b). To better understand the role of iodine in this remarkable switch of activity, a systematic investigation on the halogenation of vanillamides, a class of compounds structurally simpler than resiniferonoids, was carried out. The results showed that (a) the antagonistic activity depends on the site of halogenation and is maximal at C-6′, (b) iodine is more efficient than chlorine and bromine at reverting the agonistic activity, and (c) iodine-carbon exchange decreases antagonist activity. Iodine-induced reversal of vanilloid activity was also observed in vanillamides more powerful than capsaicin, but a poor correlation was found between agonistic and antagonistic potencies, suggesting that differences exist in the way vanillamides and their 6′-iodo derivatives bind to TRPV1.″
