- Exceptional Substrate Diversity in Oxygenation Reactions Catalyzed by a Bis(μ-oxo) Copper Complex
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The enzyme tyrosinase contains a reactive side-on peroxo dicopper(II) center as catalytically active species in C?H oxygenation reactions. The tyrosinase activity of the isomeric bis(μ-oxo) dicopper(III) form has been discussed controversially. The synthesis of bis(μ-oxo) dicopper(III) species [Cu2(μ-O)2(L1)2](X)2 ([O1](X)2, X=PF6?, BF4?, OTf?, ClO4?), stabilized by the new hybrid guanidine ligand 2-{2-((dimethylamino)methyl)phenyl}-1,1,3,3-tetramethylguanidine (L1), and its characterization by UV/Vis, Raman, and XAS spectroscopy, as well as cryo-UHR-ESI mass spectrometry, is described. We highlight selective oxygenation of a plethora of phenolic substrates mediated by [O1](PF6)2, which results in mono- and bicyclic quinones and provides an attractive strategy for designing new phenazines. The selectivity is predicted by using the Fukui function, which is hereby introduced into tyrosinase model chemistry. Our bioinspired catalysis harnesses molecular dioxygen for organic transformations and achieves a substrate diversity reaching far beyond the scope of the enzyme.
- Paul, Melanie,Teubner, Melissa,Grimm-Lebsanft, Benjamin,Golchert, Christiane,Meiners, Yannick,Senft, Laura,Keisers, Kristina,Liebh?user, Patricia,R?sener, Thomas,Biebl, Florian,Buchenau, S?ren,Naumova, Maria,Murzin, Vadim,Krug, Roxanne,Hoffmann, Alexander,Pietruszka, J?rg,Ivanovi?-Burmazovi?, Ivana,Rübhausen, Michael,Herres-Pawlis, Sonja
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supporting information
p. 7556 - 7562
(2020/05/29)
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- Selective butyrylcholine esterase inhibitor or pharmaceutically acceptable salt thereof, and preparation method and application thereof
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The invention discloses a selective butyrylcholine esterase inhibitor represented by a general formula (I) or a pharmaceutically acceptable salt thereof, and a preparation method and an application thereof. Butyrylcholine esterase inhibitory activity, sel
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Paragraph 0044-0046
(2020/01/12)
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- New phenylaniline derivatives as modulators of amyloid protein precursor metabolism
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The chloroquinoline scaffold is characteristic of anti-malarial drugs such as chloroquine (CQ) or amodiaquine (AQ). These drugs are also described for their potential effectiveness against prion disease, HCV, EBV, Ebola virus, cancer, Parkinson or Alzheimer diseases. Amyloid precursor protein (APP) metabolism is deregulated in Alzheimer's disease. Indeed, CQ modifies amyloid precursor protein (APP) metabolism by precluding the release of amyloid-beta peptides (Aβ), which accumulate in the brain of Alzheimer patients to form the so-called amyloid plaques. We showed that AQ and analogs have similar effects although having a higher cytotoxicity. Herein, two new series of compounds were synthesized by replacing 7-chloroquinolin-4-amine moiety of AQ by 2-aminomethylaniline and 2-aminomethylphenyle moieties. Their structure activity relationship was based on their ability to modulate APP metabolism, Aβ release, and their cytotoxicity similarly to CQ. Two compounds 15a, 16a showed interesting and potent effect on the redirection of APP metabolism toward a decrease of Aβ peptide release (in the same range compared to AQ), and a 3–10-fold increased stability of APP carboxy terminal fragments (CTFα and AICD) without obvious cellular toxicity at 100 μM.
- Gay, Marion,Carato, Pascal,Coevoet, Mathilde,Renault, Nicolas,Larchanché, Paul-Emmanuel,Barczyk, Amélie,Yous, Sa?d,Buée, Luc,Sergeant, Nicolas,Melnyk, Patricia
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p. 2151 - 2164
(2018/03/23)
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- N-Carbomethoxy-N-methoxy-(2-chloromethyl)-anilines, their preparation and their use as precursors for preparing 2-(pyrazol-3'-yloxymethylene)-anilides
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The present invention relates to N-carbomethoxy-N-methoxy-(2-chloromethyl)-aniline compounds of the formula I, wherein: n is 0, 1, 2 or 3, each R1 is independently selected from halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy. The invention also relates to processes and intermediates for preparing such compounds of formula I. The invention furthermore relates to processes for preparing 2-(pyrazol-3′-yloxymethylene)-anilides in which compounds of formula I are applied as precursors.
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Page/Page column 12
(2013/02/28)
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- N-CARBOMETHOXY-N-METHOXY-(2-CHLOROMETHYL)-ANILINES, THEIR PREPARATION AND THEIR USE AS PRECURSORS FOR PREPARING 2-(PYRAZOL-3'-YLOXYMETHYLENE)-ANILIDES
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The present invention relates to N-carbomethoxy-N-methoxy-(2-chloromethyl)-aniline compounds of the formula I, wherein: n is 0, 1, 2 or 3, each R1 is independently selected from halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4- alkoxy or C1-C4-haloalkoxy. The invention also relates to processes and intermediates for preparing such compounds of formula I. The invention furthermore relates to processes for preparing 2-(pyrazol-3'-yloxymethylene)-anilides in which compounds of formula I are applied as precursors.
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Page/Page column 29-30
(2011/10/10)
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- Studies on the synthesis of bis-quaternary ammonium salts of geometrical isomers and its potential as bioregulators
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Tertiary amine N,N-dimethyl-2-nitrophenylmethanamine 4 prepared from 2-nitrobenzaldehyde 3 by Leuckart's reaction and (3-N,N-diethylamino-2- hydroxypropyl)-3-(3-nitrophenyl) prop-2-en-oate 9 and 3-(diethylamino)-2- hydroxypropyl 2-(4-chloro-3-methylphenoxy)acetate 14 prepared through the formation of glycidyl ester have been reacted with dichlorides of maleic acid and fumaric acid, which in turn have been prepared by reacting these acids with thionyl chloride to get bis-quaternary ammonium salts 1a-c and 2a-c. The synthesized salts 1a-c and 2a-c are tested on rice (Oryza sativa, PR-114) for their biological activity. All the tested compounds are found to possess good plant growth retardant activity. Compound 2c is found to be the best plant growth retardant among the six newly synthesized compounds.
- Seth, Anubhuti,Rani, Simmi,Garg, Anita,Sharma
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experimental part
p. 290 - 298
(2011/05/02)
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- Mono-nitration of aromatic compounds via their nitric acid salts
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Aromatic compounds bearing a basic nitrogen atom can be converted to the corresponding nitric acid salts. Mono-nitration of the compounds can be carried out by adding a dichloromethane solution of the salts to sulfuric acid, or by adding acetyl chloride (or trifluoroacetic anhydride) to a dichloromethane solution of the salts. This protocol provides, among other benefits, the most convenient and reliable way for the prevention of over-/under-nitration and is especially suitable for scale-up.
- Zhang, Pingsheng,Cedilote, Miall,Cleary, Thomas P.,Pierce, Michael E.
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p. 8659 - 8664
(2008/03/30)
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- SUBSTITUTED N-ARYL-9-OXO-9H-FLUORENE-1-CARBOXAMIDES AND ANALOGS AS ACTIVATOR OF CASPASES AND INDUCERS OF APOPTOSIS
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The present invention is directed to substituted N-aryl-9-oxo-9H-fluorene-1-carboxamides and analogs thereof, represented by the general Formula I: (I) wherein R1-R8, X and Ar are defined herein. The present invention also relates to the discovery that co
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Page/Page column 41-43
(2010/10/20)
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