- INHIBITORS OF STEAROYL-COA DESATURASE
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Provided herein are compounds of the formula (I): as well as pharmaceutically acceptable salts thereof, wherein the substituents are as those disclosed in the specification. These compounds, and the pharmaceutical compositions containing them, are useful for the treatment of diseases such as, for example, obesity.
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- Organometallic control over the regiospecificity of functionalization reactions: 1,2,3-Trifluorobenzene and bromo derivatives thereof as substrates
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In a case study, 1,2,3-trifluorobenzene was functionalized at each of the two vacant positions (producing the benzoic acids 1 and 2) and, in addition, bromine was introduced into all available positions (producing the benzoic acids 3-5). The required regioflexibility was achieved by applying novel organometallic recipes such as deprotonation-triggered halogen migrations and site-discriminating competitive halogen-metal permutations. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.
- Heiss, Christophe,Schlosser, Manfred
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p. 447 - 451
(2007/10/03)
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- Fragmentation of radical anions of polyfluorinated benzoates
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A comprehensive study of the symmetry forbidden fragmentation of short-lived radical anions (RAs) has been undertaken for the complete set of polyfluorinated benzoates (C6FnH5-nCO22, n = 1-5). The decay rate constants (kc) of RAs have been determined in aqueous alkaline solution (pH 13.4) by electron photoinjection (EPI) from mercury electrodes and were found to increase dramatically from ≤3 × 103 s-1 (3-F - C6H4CO2-) to (1.2 ± 0.8) × 109 s-1 (C6F5CO2-). The regioselectivity of C-F bond cleavage in the RA fragmentation has been revealed by structure assignment of reduction products of the polyfluorinated benzoic acids by Na, K, and Zn in liquid NH3, as well as by Zn in aqueous NH3 and aqueous alkaline solutions. The kc values depend on the position of the cleaved fluorine to the CO2- group generally in the order para > ortho > meta, and to sharply increase if adjacent fluorine atoms are present. The observed trends reveal that the kinetics of the RA fragmentation reaction is not controlled by the reaction thermodynamics. Semiempirical UHF/INDO calculations, the validity of which has been confirmed by ab initio ROHF/6-31+G calculations, were done to rationalize the observed trends. The reaction transition state (TS) was considered to arise from the RA's and 2*states crossing avoided due to out-of-plane deviation of the cleaving C-F bond. The satisfactory linear correlation (R = 0.96) between the model reaction energy barrier Ea and log kc has been achieved with modeling the local solvation of the CO2- group by its protonation.
- Konovalov, Valery V.,Laev, Sergey S.,Beregovaya, Irina V.,Shchegoleva, Lyudmila N.,Shteingarts, Vitalij D.,Tsvetkov, Yuri D.,Bilkis, Itzhak
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p. 352 - 361
(2007/10/03)
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- Elemental fluorine. Part 1. Synthesis of fluoroaromatic compounds
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Direct fluorination of 4-fluorobenzoic acid, as a model substrate in a variety of reaction media, shows that 98% formic acid and concentrated sulfuric acid are excellent for promoting electrophilic fluorination. A high degree of fluorination may be achieved using concentrated sulfuric acid, showing that in this medium fluorine will act as a powerful electrophile.
- Chambers, Richard D.,Skinner, Christopher J.,Hutchinson, John,Thomson, Julie
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p. 605 - 609
(2007/10/03)
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