1620-77-5Relevant academic research and scientific papers
Compounds with Bridgehead Nitrogen
Crabb, Trevor A.,Heywood, Geoffrey C.
, p. 242 - 248 (1982)
The position of conformational equilibra in 1,5-,1,6- and 1,8-dimethylperhydro-oxazolopyridines were determined by 1H NMR spectroscopy.The cis-(H-5,H-8a)-1,5-dimethylperhydro-oxazolopyridines adopted the trans fused conformation, as did the two isomers of cis-(H-1,H-8a)-1,6-dimethyl-perhydro-oxazolopyridine.In contrast, r-1,t-6,t-8a-1,6-dimethyl-perhydro-oxazolopyridine preferred the cis-fused conformation.Three of the 1,8-dimehylperhdro-oxazolopyridines adopted the trans-fused conformations (with distortion of the system in the case of the r-1,c-8,c-8a derivative) and the r-1,c-8,c-8a-1,8-dimethyl derivative adopted the cis-fused conformation.
Nickel/Photoredox-Catalyzed Methylation of (Hetero)aryl Chlorides Using Trimethyl Orthoformate as a Methyl Radical Source
Kariofillis, Stavros K.,Shields, Benjamin J.,Tekle-Smith, Makeda A.,Zacuto, Michael J.,Doyle, Abigail G.
supporting information, p. 7683 - 7689 (2020/04/22)
Methylation of organohalides represents a valuable transformation, but typically requires harsh reaction conditions or reagents. We report a radical approach for the methylation of (hetero)aryl chlorides using nickel/photoredox catalysis wherein trimethyl orthoformate, a common laboratory solvent, serves as a methyl source. This method permits methylation of (hetero)aryl chlorides and acyl chlorides at an early and late stage with broad functional group compatibility. Mechanistic investigations indicate that trimethyl orthoformate serves as a source of methyl radical via β-scission from a tertiary radical generated upon chlorine-mediated hydrogen atom transfer.
NOVEL PYRIDINE DERIVATIVES
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Page/Page column 44, (2013/02/27)
The invention relates to a compound of formula (I) wherein R1 to R4 are defined as in the description and in the claims. The compound of formula (I) can be used as a medicament.
PYRIDIN- 2 -AMIDES USEFUL AS CB2 AGONISTS
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Page/Page column 100, (2013/02/27)
The invention relates to a compound of formula (I) wherein R1 to R4 are defined as in the description and in the claims. The compound of formula (I) can be used as a medicament.
A COMPOUND FOR INHIBITING HUMAN 11-β-HYDROXY STEROID DEHYDROGENASE TYPE 1, AND A PHARMACEUTICAL COMPOSITION COMPRISING THE SAME
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Page/Page column 41-42, (2012/10/08)
The present invention relates to a novel compound, or a stereoisomer, or a pharmaceutically acceptable salt thereof, and a pharmaceutical composition for human-11-beta-hydroxysteroid dehydrogenase type 1 (11β-HSD1) comprising the same. The invention provides a compound, which has excellent activity and solubility and is more efficiently formulated and delivered, and a pharmaceutical composition for human-11-beta-hydroxysteroid dehydrogenase type 1 comprising the same.
Manganese oxide promoted liquid-phase aerobic oxidative amidation of methylarenes to monoamides using ammonia surrogates
Wang, Ye,Yamaguchi, Kazuya,Mizuno, Noritaka
supporting information; experimental part, p. 7250 - 7253 (2012/08/28)
In the presence of amorphous MnO2, various methylarenes (even with two or more methyl groups) could be selectively converted into the corresponding primary monoamides in moderate to high yields. The observed catalysis was truly heterogeneous, and the retrieved amorphous MnO2 catalyst could be reused without an appreciable loss of its catalytic performance. Copyright
Per-6-amino-β-cyclodextrin/CuI catalysed cyanation of aryl halides with K4[Fe(CN)6]
Azath, Ismail Abulkalam,Suresh, Palaniswamy,Pitchumani, Kasi
supporting information, p. 2334 - 2339 (2013/01/15)
Efficient cyanation of aryl halides is achieved using less toxic K 4[Fe(CN)6] as the reagent and amino-β-cyclodextrins as supramolecular ligands for CuI. Four different amino cyclodextrins viz. per-6-amino-β-CD, per-6-methylamino-β-CD, per-6-butyl-amino-β-CD and mono-6-amino-β-CD are prepared and studied. Aryl and heteroaryl nitriles are obtained in good to excellent yield for even bromo derivatives of flavone and 2-aminopyrans. This system uses catalytic amounts (10 mol%) of both copper iodide and per-6-amino-β-cyclodextrin. Easy separation, the absence of nitrogen atmosphere and excellent yield are the other significant outcomes of this protocol. The Royal Society of Chemistry and the Centre National de la Recherche Scientifique.
NOVEL FXR (NR1H4 ) BINDING AND ACTIVITY MODULATING COMPOUNDS
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Page/Page column 57; 58, (2011/04/13)
The present invention relates to compounds which bind to the NR1 H4 receptor (FXR) and act as agonists of the NR1 H4 receptor (FXR). The invention further relates to the use of the compounds for the preparation of a medicament for the treatment of diseases and/or conditions through binding of said nuclear receptor by said compounds, and to a process for the synthesis of said compounds.
Novel FXR (NR1H4) binding and activity modulating compounds
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Page/Page column 26, (2011/04/14)
The present invention relates to compounds which bind to the NR1H4 receptor (FXR) and act as agonists of the NR1H4 receptor (FXR). The invention further relates to the use of the compounds for the preparation of a medicament for the treatment of diseases and/or conditions through binding of said nuclear receptor by said compounds, and to a process for the synthesis of said compounds.
Reduction of a redox-active ligand drives switching in a Cu(I) pseudorotaxane by a bimolecular mechanism
McNitt, Kristy A.,Parimal, Kumar,Share, Andrew I.,Fahrenbach, Albert C.,Witlicki, Edward H.,et al.
supporting information; experimental part, p. 1305 - 1313 (2009/06/28)
The reduction of a redox-active ligand is shown to drive reversible switching of a Cu(I) [2]pseudorotaxane ([2]PR + ) into the reduced [3]pseudorotaxane ([3]PR + ) by a bimolecular mechanism.The unreduced pseudorotaxanes [2]PR + and [3]PR 2+ are initially self-assembled from the binucleating ligand, 3,6-bis(5-methyl-2-pyridine)-1,2,4, 5-tetrazine (Me 2 BPTZ), and a preformed copper-macrocycle moiety (Cu-M + ) based on 1,10-phenanthroline. X-raycrystallography revealed a syn geometry of the [3]PR 2+ .The U V-vis-NIR spectra show low-energy metal-to-ligand charge-transfer transitions that red shift from 808 nm for [2]PR+ to 1088 nm for [3]PR 2+ . Quantitative analysis of the UV-vis-NIR titration shows the stepwise formation constants to be K 1 = 8.9 × 10 8 M -1 and K 2 = 3.1 × 10 + M -1, indicative of negative cooperativity. The cyclic voltammetry (CV)and coulometry of Me 2 BPTZ, [2]PR + , and [3]PR 2+ shows the one-electron reductions at E 1/2 = -0.96, -0.65, and -0.285 V, respectively, to be stabilized in a stepwise manner by each Cu+ ion. CVs of [2]PR + show changes with scan rate consistent with an EC mechanism of supramolecular disproportionation afterreduction: [2]PR 0 + [2]PR + = [3]PR + + Me 2 BPTZ 0 (K D * , Ad). UV-vis- NIR spectroelectrochemistry was used to confirm the 1:1 product stoichiometry for [3]PR + :Me 2 BPTZ. The driving force (δG D = -5.1 kcal mol -1 ) for the reaction is based on the enhanced stability of the reduced [3]PR + over reduced [2]PR 0 by 365 mV (8.4 kcal mol -1 ). Digital simulations of the CVs are consistent with a bimolecular pathway (K d = 12 000 s + M -1 ). Confirmation of the mechanism p rovides a basis to extend this new switching modality to molecular machines.
