65620-72-6Relevant academic research and scientific papers
Structural and in Vitro Functional Characterization of a Menthyl TRPM8 Antagonist Indicates Species-Dependent Regulation
Journigan, V. Blair,Alarcón-Alarcón, David,Feng, Zhiwei,Wang, Yuanqiang,Liang, Tianjian,Dawley, Denise C.,Amin, A. R. M. Ruhul,Montano, Camila,Van Horn, Wade D.,Xie, Xiang-Qun,Ferrer-Montiel, Antonio,Fernández-Carvajal, Asia
supporting information, p. 758 - 767 (2021/05/04)
TRPM8 antagonists derived from its cognate ligand, (-)-menthol, are underrepresented. We determine the absolute stereochemistry of a well-known TRPM8 antagonist, (-)-menthyl 1, using VCD and 2D NMR. We explore 1 for its antagonist effects of the human TRPM8 (hTRPM8) orthologue to uncover species-dependent inhibition versus rat channels. (-)-Menthyl 1 inhibits menthol- and icilin-evoked Ca2+ responses at hTRPM8 with IC50 values of 805 ± 200 nM and 1.8 ± 0.6 μM, respectively, while more potently inhibiting agonist responses at the rat orthologue (rTRPM8 IC50 (menthol) = 117 ± 18 nM, IC50 (icilin) = 521 ± 20 nM). Whole-cell patch-clamp recordings of hTRPM8 confirm the 1 inhibition of menthol-stimulated currents, with an IC50 of 700 ± 200 nM. We demonstrate that 1 possesses ≥400-fold selectivity for hTRPM8 versus hTRPA1/hTRPV1. (-)-menthyl 1 can be used as a novel chemical tool to study hTRPM8 pharmacology and differences in species commonly used in drug discovery.
Atypical and Asymmetric 1,3-P,N Ligands: Synthesis, Coordination and Catalytic Performance of Cycloiminophosphanes
Rong, Mark K.,Holtrop, Flip,Bobylev, Eduard O.,Nieger, Martin,Ehlers, Andreas W.,Slootweg, J. Chris,Lammertsma, Koop
, p. 14007 - 14016 (2021/09/09)
Novel seven-membered cyclic imine-based 1,3-P,N ligands were obtained by capturing a Beckmann nitrilium ion intermediate generated in situ from cyclohexanone with benzotriazole, and then displacing it by a secondary phosphane under triflic acid promotion. These “cycloiminophosphanes” possess flexible non-isomerizable tetrahydroazepine rings with a high basicity; this sets them apart from previously reported iminophophanes. The donor strength of the ligands was investigated by using their P-κ1- and P,N-κ2-tungsten(0) carbonyl complexes, by determining the IR frequency of the trans-CO ligands. Complexes with [RhCp*Cl2]2 demonstrated the hemilability of the ligands, giving a dynamic equilibrium of κ1 and κ2 species; treatment with AgOTf gives full conversion to the κ2 complex. The potential for catalysis was shown in the RuII-catalyzed, solvent-free hydration of benzonitrile and the RuII- and IrI-catalyzed transfer hydrogenation of cyclohexanone in isopropanol. Finally, to enable access to asymmetric catalysts, chiral cycloiminophosphanes were prepared from l-menthone, as well as their P,N-κ2-RhIII and a P-κ1-RuII complexes.
Synthesis of nitrogen-containing monoterpenoids with antibacterial activity
Grabowiecka, Agnieszka,Grela, Ewa,Macegoniuk, Katarzyna,Kozio?, Agata,Lochyński, Stanis?aw
supporting information, p. 1074 - 1079 (2019/01/29)
Incorporation of the Beckmann rearrangement into the presented research resulted in the formation of nitrogen-containing terpenoid derivatives originating from naturally occurring compounds. Both starting monoterpenes and obtained derivatives were subjected to estimation of their antibacterial potential. In the presented study, Staphylococcus aureus was the most sensitive to examined compounds. The Minimal Inhibitory Concentration (MIC) experiments performed on S. aureus demonstrated that the (?)-menthone oxime (?)-8 and (+)-pulegone oxime (+)-13 had the best antibacterial activity among the tested derivatives and starting compounds. Their MIC90 value was 100 μg/mL. The obtained derivatives were also evaluated for their inhibitory activity against bacterial urease. Among the tested compounds, three active inhibitors were found–oxime 14 and lactams (?)-15 and 16 limited the activity of Sporosarcina pasteurii urease with Ki values of 174.3 μM, 43.0 μM and 4.6 μM, respectively. To our knowledge, derivative 16 is the most active antiureolytic lactam described to date.
Tandem and Selective Conversion of Tetrahydropyranyl and Silyl Ethers to Oximes Catalyzed with Trichloroisocyanuric Acid
Aghapour, Ghasem,Abbaszadeh, Zeinab
, p. 1464 - 1470 (2015/09/01)
Direct and oxidative conversion of tetrahydropyranyl and silyl ethers to oximes is described using trichloroisocyanuric acid (TCCA) as a relatively stable and inexpensive oxidant surprisingly in a catalytic amount and hydroxylamine hydrochloride under solvent-free conditions. Oximes can be synthesized from these protected alcohols in the presence of some other functional groups with excellent chemoselectivity using the present tandem catalytic method.
Europium(III) triflate-catalyzed Trofimov synthesis of polyfunctionalized pyrroles
Madabhushi, Sridhar,Vangipuram, Venkata Sairam,Mallu, Kishore Kumar Reddy,Chinthala, Narsaiah,Beeram, China Ramanaiah
supporting information; body text, p. 1413 - 1416 (2012/07/13)
The synthesis of polyfunctionalized pyrroles by reaction of a ketoxime with dimethyl acetylenedicarboxylate using europium(III) triflate as the catalyst is described. Copyright
Efficient and stereodivergent electrochemical synthesis of optically pure menthylamines
Kulisch, Joern,Nieger, Martin,Stecker, Florian,Fischer, Andreas,Waldvogel, Siegfried R.
supporting information; experimental part, p. 5564 - 5567 (2011/07/30)
The cathode directs the way to the epimeric menthylamines. The reduction of menthone oxime on a Hg cathode generates (-)-menthylamine as the major product, whereas a Pb cathode gives access to (+)-neomenthylamine (see scheme). Insitu decoration of the Pb cathode by small amounts of additives results in clean and quantitative conversions. Furthermore, Pb corrosion is completely prevented in this practical method. Copyright
Asymmetric hydroamination catalyzed by in situ generated chiral amidate and ureate complexes of zirconium - Probing the role of the tether in ligand design
Payne, Philippa R.,Bexrud, Jason A.,Leitch, David C.,Schafer, Laurel L.
experimental part, p. 1222 - 1229 (2012/02/06)
Simple chiral proligands have been synthesized from inexpensive chiral starting materials. These amidate and ureate ligands support zirconium complexes that successfully catalyze intramolecular hydroamination with up to 26% ee. Several elements necessary for successful ligand design are highlighted and discussed. In particular, the strict control of metal geometry through multidentate tethered ligands is determined to be an essential aspect of future ligand development.
LIQUID CHROMATOGRAPHIC RESOLUTION OF RACEMIC KETONES AS THEIR OXIME 3,5-DINITROPHENYL CARBAMATES ON A CHIRAL STATIONARY PHASE
Hyun, Myung Ho,Park, Young -Whan,Baik, In-Kyu
, p. 4735 - 4738 (2007/10/02)
Cyclic and acyclic chiral ketones have been resolved as their oxime 3,5-dinitrophenyl carbamates on a chiral stationary phase derived from (S)-1-(6,7-dimethyl-1-naphthyl)isobutylamine.
C-Nitroso compounds. Part XXXVIII. Radical reactions of α-chloro-nitroso compounds with trialkylaluminium-ether complexes
Lub, J.,Beekes, M. L.,Boer, Th. J. de
, p. 161 - 167 (2007/10/02)
Ether complexes of trialkylaluminium compounds react with α-chloro-nitroso compounds via radicals which can abstract hydrogen from various solvents.In the presence of olefinic solvents, radical addition to the double bond also takes place. When the trialk
