33026-74-3Relevant academic research and scientific papers
Synthesis and SAR of 1-hydroxy-1 H -benzo[ d ]imidazol-2(3 H)-ones as inhibitors of d -amino acid oxidase
Berry, James F.,Rais, Rana,Slusher, Barbara S.,Tsukamoto, Takashi,Ferraris, Dana V.,Duvall, Bridget,Hin, Niyada,Alt, Jesse,Thomas, Ajit G.,Rojas, Camilo,Hashimoto, Kenji
supporting information, p. 839 - 843,5 (2020/09/15)
A series of 1-hydroxy-1H-benzo[d]imidazol-2(3H)-ones were synthesized and evaluated for their ability to inhibit human and porcine forms of d-amino acid oxidase (DAAO). The inhibitory potency is largely dependent on the size and position of substituents o
Investigating N-methoxy-N′-aryl ureas in oxidative C-H olefination reactions: An unexpected oxidation behaviour
Willwacher, Jens,Rakshit, Souvik,Glorius, Frank
supporting information; experimental part, p. 4736 - 4740 (2011/08/06)
Herein, we report a urea derived directing group for mild and highly selective oxidative C-H bond olefination. Subsequent intramolecular Michael addition affords dihydroquinazolinones in good yields. The N-O bond of the urea substrate exhibits superior oxidative behaviour compared to a variety of other external oxidants. The Royal Society of Chemistry 2011.
Synthesis of N-alkoxybenzimidoyl azides and their reactions in electrophilic media
Dolliver, Debra D.,Sommerfeld, Thomas,Lanier, Megan L.,Dinser, Jordan A.,Rucker, Richard P.,Weber, Rebecca J.,McKim, Artie S.
experimental part, p. 227 - 237 (2010/09/07)
A new general route to N-alkoxybenzimidoyl azides [ArC(N3)=NOR] from a reaction of N-alkoxybenzimidoyl bromide [ArC(Br)=NOR] with sodium azide in DMSO is described. These reactions result in the Z-geometric configuration. These compounds show a moderate degree of thermal stability as assessed by differential scanning calorimetry, and lack reactivity in traditional 1,3-dipolar cycloaddition 'click' reactions. Upon exposure to electrophilic compounds (trifluoroacetic acid or acetyl chloride), these azide compounds can react by two pathways: a Schmidt-type rearrangement to form an N-alkoxyurea or an isomerization - cyclization reaction pathway to form an N-alkoxytetrazole. The route of the reaction has no dependence on solvent polarity and appears to depend upon the electrophile (H+ vs. CH3CO+): reaction of the azide with trifluoroacetic acid results predominantly in the urea; reaction with acetyl chloride results solely in the tetrazole. Calculations indicate that the urea product is thermodynamically favored over the tetrazole product. They also indicate that both reaction conditions result in an equilibration between the starting azide and the tetrazole with the tetrazole being the major component in this equilibrium mixture. The fact that the azide also undergoes a Schmidt-type rearrangement to form an N-alkoxyurea when treated with trifluoroacetic acid appears to indicate that the barrier for aromatic ring migration is lower in the protonated azide produced on reaction with trifluoroacetic acid than in the acetylated azide produced on reaction with acetyl chloride. Copyright
Analogues of N-hydroxy-N′-phenylthiourea and N-hydroxy-N′-phenylurea as inhibitors of tyrosinase and melanin formation
Criton, Marc,Le Mellay-Hamon, Veronique
body text, p. 3607 - 3610 (2009/04/06)
A series of N-hydroxy-N′-phenylthiourea and N-hydroxy-N′-phenylurea analogues were prepared and evaluated as inhibitors of tyrosinase and melanin formation. The most active analogue 1 inhibited mushroom tyrosinase with an IC50 of around 0.29 μM
KINETICS AND MECHANISM OF HYDROLYSIS OF ARYL N-METHOXYCARBAMATES AND THEIR DERIVATIVES
Mindl, Jaromir,Sterba, Vojeslav
, p. 900 - 905 (2007/10/02)
Hydrolysis kinetics have been studied of 3- and 4-substituted phenyl N-methoxycarbamates and their N-methyl derivatives in aqueous buffers at 60 deg C.The N-methyl derivatives show linear dependence of the rate constants on concentration of hydroxyl ion in the pH range measured.Hydrolysis of aryl N-methoxycarbamates is independent of hydroxyl ion concentration at higher pH values.Logarithms of the rate constants have been correlated with the substituent constants ?.The calculated values 0.9 for N-methyl derivatives, 4.5 and 3.3 for aryl N-methoxy-carbamates in theregions of linear pH-dependency and pH-independency, respectively, suggest that the hydrolysis follows the BAc2 and ElcB mechanisms in the case of the N-methyl derivatives and aryl N-methoxycarbamates, respectively.Difference between the two ρ constants for the hydrolysis of aryl N-methoxycarbamates agrees with the found value ρ=1.2 for dissociation constants of these compounds.The elimination mechanism has been confirmed by reaction of the isocyanate formed with added aniline to give the respective urea.
APPROACH TO THE 1-METHOXY-2-BENZIMIDAZOLINONES
Perronnet, Jacques,Demoute, Jean-Pierre
, p. 507 - 512 (2007/10/02)
With t-butyl hypochlorite the 1-methoxy-3-arylureas are easily converted into the unstable corresponding 1-chloro-1-methoxy-3-arylureas.Cyclization of the latter under basic conditions gives the 1-methoxy-2-benzimidazolinones.The two steps can be carried
