350-53-8Relevant academic research and scientific papers
A Photoswitchable Agonist for the Histamine H3 Receptor, a Prototypic Family A G-Protein-Coupled Receptor
Hauwert, Niels J.,Mocking, Tamara A. M.,Da Costa Pereira, Daniel,Lion, Ken,Huppelschoten, Yara,Vischer, Henry F.,De Esch, Iwan J. P.,Wijtmans, Maikel,Leurs, Rob
supporting information, p. 4531 - 4535 (2019/03/07)
Spatiotemporal control over biochemical signaling processes involving G protein-coupled receptors (GPCRs) is highly desired for dissecting their complex intracellular signaling. We developed sixteen photoswitchable ligands for the human histamine H3 receptor (hH3R). Upon illumination, key compound 65 decreases its affinity for the hH3R by 8.5-fold and its potency in hH3R-mediated Gi protein activation by over 20-fold, with the trans and cis isomer both acting as full agonist. In real-time two-electrode voltage clamp experiments in Xenopus oocytes, 65 shows rapid light-induced modulation of hH3R activity. Ligand 65 shows good binding selectivity amongst the histamine receptor subfamily and has good photolytic stability. In all, 65 (VUF15000) is the first photoswitchable GPCR agonist confirmed to be modulated through its affinity and potency upon photoswitching while maintaining its intrinsic activity, rendering it a new chemical biology tool for spatiotemporal control of GPCR activation.
Enantioselective Oxidative Coupling of β-Ketocarbonyls and Anilines by Joint Chiral Primary Amine and Selenium Catalysis
Chen, Wanting,Wang, Yanni,Mi, Xueling,Luo, Sanzhong
supporting information, p. 8178 - 8182 (2019/10/16)
An enantioselective primary amine-catalyzed total N-selective nitroso aldol reaction (N-NA) was achieved through the oxidation of primary aromatic amines to the corresponding nitrosoarenes catalyzed by selenium reagents and 30% H2O2. This protocol provides a facile and highly efficient access to α-hydroxyamino carbonyls bearing chiral quaternary centers under exceedingly mild and green reaction conditions with high chemo-and enantiocontrol.
Anion ligand promoted selective C-F bond reductive elimination enables C(sp2)-H fluorination
Mao, Yang-Jie,Luo, Gen,Hao, Hong-Yan,Xu, Zhen-Yuan,Lou, Shao-Jie,Xu, Dan-Qian
supporting information, p. 14458 - 14461 (2019/12/09)
A detailed mechanism study on the anion ligand promoted selective C-H bond fluorination is reported. The role of the anion ligand has been clarified by experimental evidence and DFT calculations. Moreover, the nitrate promoted C-F bond reductive elimination enabled a selective C-H bond fluorination of various symmetric and asymmetric azobenzenes to access diverse o-fluoroanilines.
Coupling of N -Nosylhydrazones with Nitrosoarenes: Transition-Metal-Free Approach to (Z)- N -Arylnitrones
Liu, Tingting,Liu, Zhaohong,Liu, Zhenhua,Hu, Donghua,Wang, Yeming
supporting information, p. 1728 - 1736 (2018/02/14)
An efficient and transition-metal-free protocol for the synthesis of (Z)- N -arylnitrones from the direct coupling of N -nosylhydrazones with nitrosoarenes under mild conditions is described. The protocol is compatible with a wide range of functional groups placed on both the reagents and provided the corresponding nitrones in good to excellent yields by simple recrystallization process. The use of these 1,3-dipoles for the synthesis of substituted indoles is elaborated for 2,3-diphenyl-1 H -indole.
A lewis acid catalyzed annulation to 2,1-benzisoxazoles
Otley, Kate D.,Ellman, Jonathan A.
, p. 8296 - 8303 (2015/03/18)
We report here a new, atom economical annulation to 2,1-benzisoxazole scaffolds via the BF3·Et2O-catalyzed reaction of glyoxylate esters and nitrosoarenes. The developed method represents a convergent route to this compound class from previously unexplored inputs and provides a range of 2,1-benzisoxazoles in moderate to high yields under convenient conditions. Along with exploration of substrate scope, initial mechanistic investigation through 18O labeling and the synthesis of a reaction intermediate provides evidence for an unusual umpolung addition of glyoxylates to nitrosobenzenes with high O-selectivity, followed by a new type of Friedel-Crafts cyclization.
Selective N-oxidation of aromatic amines to nitroso derivatives using a molybdenum acetylide oxo-peroxo complex as catalyst
Biradar, Ankush V.,Kotbagi, Trupti V.,Dongare, Mohan K.,Umbarkar, Shubhangi B.
, p. 3616 - 3619 (2008/09/19)
The molybdenum acetylide oxo-peroxo complex obtained in situ by the treatment of the corresponding molybdenum acetylide carbonyl complex, CpMo(CO)3(C{triple bond, long}CPh); Cp = η5-C5H5 with H2O2, has been used as an efficient catalyst for selective N-oxidation of primary amines to nitroso derivatives. Excellent amine conversion (up to 100%) and very high selectivity for nitroso compounds (99%) have been obtained using 30% hydrogen peroxide as an oxidant. The oxo peroxo Mo(VI) complex has also been found to be very active for the oxidation of various substituted primary aromatic amines with electron donating as well as electron withdrawing substituents on the aromatic ring.
Structural investigations of C-nitrosobenzenes. Part 2. NMR studies of monomer-dimer equilibria including restricted nitroso group rotation in monomers
Fletcher, Daniel A.,Gowenlock, Brian G.,Orrell, Keith G.
, p. 797 - 803 (2007/10/03)
Energy barriers associated with rotation of nitroso groups in monomeric nitrosobenzene and eleven monomeric substituted nitrosobenzenes in solution have been measured by total 1H NMR bandshape analysis. ΔG? (298.15 K) values for the rotations are in the range 31-41 kJ mol-1. The values for 4-substituted compounds correlate well with the Hammett σp+ parameter for the substituent. The experimental energy barrier for nitrosobenzene is compared with theoretical calculations. Monomerdimer equilibria of these compounds in solution have been investigated, with ΔH, ΔSominus; and ΔGominus; data calculated for the dissociation of both Z- and E- azodioxy dimers to monomers. Kinetic data, based on time-dependent and two-dimensional exchange spectroscopy (2D-EXSY) NMR measurements, have been obtained for the dissociation of 3-methylnitrosobenzene and 3,5-dimethylnitrosobenzene dimers. Energy profiles for the ground and transition states of both dimers and monomers (including exchange between both their rotameric forms) are discussed.
Structural investigations of C-nitrosobenzenes. Part 1. Solution state 1H NMR studies
Fletcher, Daniel A.,Gowenlock, Brian G.,Orrell, Keith G.
, p. 2201 - 2205 (2007/10/03)
Ambient and low temperature 1H NMR spectra of a wide range of 3- and 4-monosubstituted, and some di- and tri-substituted C-nitrosobenzenes have enabled -N=O substituent constants for the static and rotating ring molecules to be calculated. This has provided information on the shielding anisotropy of the N=O group which in turn leads to the firm identification of the monomeric and dimeric solution species. In all cases lowering the solution temperature enhances the relative populations of dimers to monomers, with the (Z)-azodioxy dimer being preferred over the (E)-form, irrespective of the nature of the solid state dimeric structure.
