16355-92-3Relevant articles and documents
Highly Selective Radical Monoreduction of Dihalides Confined to a Dynamic Supramolecular Host
Petroselli, Manuel,Rebek, Julius,Yu, Yang
, p. 3284 - 3287 (2021)
Reduction of alkyl dihalide guests (2–5 and 7) with trialkylsilanes (R3SiH) was performed in water-soluble host 1 to investigate the effects of confinement on fast radical reactions (k≥103 m?1 s?1). High selectivity (>95 %) for mono-reduced products was observed for primary and secondary dihalide guests under mild conditions. The results highlight the importance of host–guest complexation rates to modulate the product selectivity in radical reactions.
A Simple Convenient Procedure for Iodination of Alcohols and Reductive Iodination of Carbonyl Compounds using N,N-Diethylaniline-Borane-I2 system.
Reddy, Ch. Kishan,Periasamy, M.
, p. 5663 - 5664 (1989)
Alcohols, carboxylic acids and carbonyl compounds give the corresponding alkyl iodides in moderate to good yields on reaction with N,N-diethylaniline-borane complex and iodine.
Probing the Existence of a Metastable Binding Site at the β2-Adrenergic Receptor with Homobivalent Bitopic Ligands
Gaiser, Birgit I.,Danielsen, Mia,Marcher-R?rsted, Emil,R?pke J?rgensen, Kira,Wróbel, Tomasz M.,Frykman, Mikael,Johansson, Henrik,Br?uner-Osborne, Hans,Gloriam, David E.,Mathiesen, Jesper Mosolff,Sejer Pedersen, Daniel
, p. 7806 - 7839 (2019/09/07)
Herein, we report the development of bitopic ligands aimed at targeting the orthosteric binding site (OBS) and a metastable binding site (MBS) within the same receptor unit. Previous molecular dynamics studies on ligand binding to the β2-adrenergic receptor (β2AR) suggested that ligands pause at transient, less-conserved MBSs. We envisioned that MBSs can be regarded as allosteric binding sites and targeted by homobivalent bitopic ligands linking two identical pharmacophores. Such ligands were designed based on docking of the antagonist (S)-alprenolol into the OBS and an MBS and synthesized. Pharmacological characterization revealed ligands with similar potency and affinity, slightly increased β2/β1AR-selectivity, and/or substantially slower β2AR off-rates compared to (S)-alprenolol. Truncated bitopic ligands suggested the major contribution of the metastable pharmacophore to be a hydrophobic interaction with the β2AR, while the linkers alone decreased the potency of the orthosteric fragment. Altogether, the study underlines the potential of targeting MBSs for improving the pharmacological profiles of ligands.
New synthesis of (11Z,13Z)-11,13-Hexadecadienal, the female sex pheromone of the navel orangeworm
Mori, Kenji
experimental part, p. 2727 - 2730 (2010/09/11)
(11Z,13Z)-11,13-Hexadecadienal, the female sex pheromone of the navel orangeworm (Amyelois transitella), was synthesized from commercially available 10-bromo-1-decanol in a 27% overall yield (8 steps). The synthesis was achieved by using 10-iododecanal, trimethylsilylacetylene and (Z)-1-bromo-12-butene as the key building blocks, employing Sonogashira-Hagihara coupling and Brown's hydroboration-protonolysis as the key reactions. The terminal formyl group was installed in the earlier stage of the synthesis rather than in the final step. This procedure enabled the multi-gram-scale preparation of this economically important pheromone.