1126-20-1Relevant articles and documents
Formation of Dihydrobenzofurans by Radical Cyclization
Beckwith, Athelstan L. J.,Meijs, Gordon F.
, p. 136 - 137 (1981)
A survey of methods for the generation of aryl radicals from o-alkenyloxyarene diazonium salts demonstrates that dihydrobenzofuran derivatives can be efficiently formed by treatment of (1) or (2) with Bun3SnH-Et2O or with NaI-Me2CO; methods utilising the iodo-compound (3; X = I) are less effective.
Rabinowitz et al.
, p. 53 (1973)
Cyclodextrin-Promoted Radical Cyclization of o-(2-Propenyloxy)- and o-(2-Propynyloxy)-benzenediazonium Ions
Fukunishi, Koushi,Shimode, Mitsuo,Hisamune, Rie,Akita, Makoto,Kuwabara, Masaki,et al.
, p. 337 - 340 (1991)
Radical dediazoniation of o-(2-propenyloxy)- and o-(2-propynyloxy)benzenediazonium ions in the presence of β-cyclodextrin gives selectively dihydrobenzofurans under N2, while hydroxymethylated dihydrobenzofurans and 3-hydroxymethyl-benzofuran under air, respectively.
Hybridization of β-Adrenergic Agonists and Antagonists Confers G Protein Bias
Stanek, Markus,Picard, Louis-Philippe,Schmidt, Maximilian F.,Kaindl, Jonas M.,Hübner, Harald,Bouvier, Michel,Weikert, Dorothée,Gmeiner, Peter
, p. 5111 - 5131 (2019/05/28)
Starting from the β-adrenoceptor agonist isoprenaline and beta-blocker carvedilol, we designed and synthesized three different chemotypes of agonist/antagonist hybrids. Investigations of ligand-mediated receptor activation using bioluminescence resonance energy transfer biosensors revealed a predominant effect of the aromatic head group on the intrinsic activity of our ligands, as ligands with a carvedilol head group were devoid of agonistic activity. Ligands composed of a catechol head group and an antagonist-like oxypropylene spacer possess significant intrinsic activity for the activation of Gαs, while they only show weak or even no β-arrestin-2 recruitment at both β1- and β2-AR. Molecular dynamics simulations suggest that the difference in G protein efficacy and β-arrestin recruitment of the hybrid (S)-22, the full agonist epinephrine, and the β2-selective, G protein-biased partial agonist salmeterol depends on specific hydrogen bonding between Ser5.46 and Asn6.55, and the aromatic head group of the ligands.
Reagent Design and Ligand Evolution for the Development of a Mild Copper-Catalyzed Hydroxylation Reaction
Fier, Patrick S.,Maloney, Kevin M.
supporting information, p. 3033 - 3036 (2017/06/07)
Parallel synthesis and mass-directed purification of a modular ligand library, high-throughput experimentation, and rational ligand evolution have led to a novel copper catalyst for the synthesis of phenols with a traceless hydroxide surrogate. The mild reaction conditions reported here enable the late-stage synthesis of numerous complex, druglike phenols.
