13161-30-3Relevant articles and documents
Pattern of Addition of Hydroxyl Radicals to the Spin Traps α-Pyridyl 1-Oxide N-tert-Butyl Nitrone
Neta, P.,Steenken, S.,Janzen, Edward G.,Shetty, Raghav V.
, p. 532 - 534 (1980)
Hydroxyl radicals react with α-2, α-3, and α-4-pyridyl 1-oxide N-tert-butyl nitrones (POBN) with rate constants of 3.2E9, 4.8E9, and 3.5E9 M-1 s-1, respectively, via addition to two distinct sites.Addition to the pyridine ring yields short-lived radicals of the hydroxyazacyclohexadienyl type, while addition to the nitrone function in the side chain yields long-lived nitroxide radicals.The distribution of OH addition at the two molecular sites was determined by using differences in reducing power upon reaction of the different types of radicals with IrCl62-.The fraction of OH attack on the pyridine ring is ca. 0.6, relatively independent of the isomeric structure of the POBN.
Alkyl transfer with retention and inversion of configuration: Reexamination of a putative [1s,4s] sigmatropic rearrangement
Wolfe, Saul,Yang, Kiyull,Weinberg, Noham,Shi, Zheng,Hsieh, Yih-Huang,Sharma, Rajendra Dev,Ro, Stephen,Kim, Chan-Kyung
, p. 886 - 902 (1998)
The thermal rearrangement of 2-alkoxypyridine-1-oxides to 1-alkoxy-2-pyridones, which has been reported to proceed by an intramolecular [1s,4s] sigmatropic migration of the alkyl group with retention of configuration and first-order kinetics, has been reexamined. The intramolecular barriers have been computed to be at least 20 kcal mol-1 higher than the reported experimental barriers. An alternative bimolecular mechanism, discovered computationally, has been confirmed by a variety of experiments including crossover studies, determination of solvent effects and secondary H/D isotope effects, and new kinetic and stereochemical studies. In the new mechanism there is an initial intermolecular transfer of the alkyl group, with inversion of configuration, to the N-oxide. Depending on the nature of the alkyl group and the solvent, this is followed by a second transfer, also with inversion of configuration, of one of the alkyl groups of the cationic intermediate to one of the oxygens of the anionic intermediate. The product is then formed either without crossover, by a double inversion of one alkyl group, or with crossover by two single inversions of different alkyl groups. The proposed intermediates of this mechanism can be synthesized; they react to form a 1-alkoxy-2-pyridone at room temperature.
STIMULUS-TRIGGERED PRODRUGS
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Page/Page column 51-53, (2012/01/13)
Set forth herein, inter alia, are compositions and methods for treating diseases with prodrugs. Provided herein are prodrug compositions for inhibiting the function of proteins, compositions and methods for treating diseases associated with oxidative compounds, oxidatively-sensitive prodrugs of inhibitors of metalloproteases. and methods of inhibiting metalloproteases using oxidatively-sensitive prodrugs.
An efficient synthesis of heterocyclic N-oxides over molecular sieve catalyst
Prasad, M. Ramakrishna,Kamalakar, G.,Madhavi, G.,Kulkarni, S. J.,Raghavan, K. V.
, p. 1577 - 1578 (2007/10/03)
Heterocyclic N-oxides have been synthesized in very high yields over redox molecular sieve catalysts in the presence of H2O2.