119113-94-9Relevant academic research and scientific papers
A new entry to the synthesis of primin via a B-alkyl suzuki-miyaura cross-coupling reaction
Watanabe, Kazuhiro,Sugizaki, Tomohiro,Tozawa, Yumi,Katoh, Tadashi
, p. 985 - 989 (2013/08/23)
Primin, a biologically active benzoquinone natural product, was efficiently synthesized in 56% overall yield in six steps starting from commercially available 5-iodovanillin. The synthetic method involves crucial steps, including a B-alkyl Suzuki-Miyaura
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.″
Facile syntheses of building blocks for the construction of phosphotyrosine mimetics
Cockerill, G. Stuart,Easterfield, Howard J.,Percy, Jonathan M.,Pintat, Stephane
, p. 2591 - 2599 (2007/10/03)
The copper-catalysed zinc phosphonate chemistry described by Yokomatsu and Shibuya can be used to enter the classical organometallic coupling repertoire via Stille and Suzuki-Miyaura couplings. 1,4-Diiodobenzene underwent coupling with the organozinc reag
