70551-46-1Relevant articles and documents
Multivalent, sulfur-rich PyBox asterisk ligands in asymmetric metal catalysis
Aubert, Catherine,Dallaire, Carol,Pepe, Gerard,Levillain,Felix, Guy,Gingras, Marc
, p. 6145 - 6154 (2013/01/15)
Multivalent PyBox asterisk ligand 1 and monovalent ligand 2 are reported. The innovative feature in 1 is a sulfur-rich persulfurated benzene core as a template joining six PyBox units in close proximity. An efficient persulfuration of C6Cl
Synthesis and structure-activity relationships of N-{3-[2-(4-alkoxyphenoxy) thiazol-5-yl]-1-methylprop-2-ynyl}carboxy derivatives as selective acetyl-CoA carboxylase 2 inhibitors
Gu, Yu Gui,Weitzberg, Moshe,Clark, Richard F.,Xu, Xiangdong,Li, Qun,Zhang, Tianyuan,Hansen, T. Matthew,Liu, Gang,Xin, Zhili,Wang, Xiaojun,Wang, Rongqi,McNally, Teresa,Camp, Heidi,Beutel, Bruce A.,Sham, Hing L.
, p. 3770 - 3773 (2007/10/03)
A structurally novel acetyl-CoA carboxylase (ACC) inhibitor is identified from high-throughput screening. A preliminary structure-activity relationship study led to the discovery of potent dual ACC1/ACC2 and ACC2 selective inhibitors against human recombinant ACC1 and ACC2. Selective ACC2 inhibitors exhibited IC50 1000-fold selectivity against ACC1. (S)-Enantiomer 9p exhibited high ACC2 activity and lowered muscle malonyl-CoA dose-dependently in acute rodent studies, whereas (R)-enantiomer 9o was weak and had no effect on the malonyl-CoA level.
Unexpected differences in the α-halogenation and related reactivity of sulfones with perhaloalkanes in KOH-t-BuOH
Meyers, Cal Y.,Chan-Yu-King, Roch,Hua, Duy H.,Kolb, Vera M.,Matthews, Walter S.,Parady, Thomas E.,Horii, Toyokazu,Sandrock, Paul B.,Hou, Yuqing,Xie, Songwen
, p. 500 - 511 (2007/10/03)
Most alkyl phenyl sulfones are readily α-chlorinated with CCl4 and α-brominated with CBrCl3 in KOH-t-BuOH via radical-anion radical pair (RARP) reactions. While isopropyl mesityl sulfone (4) is easily α-chlorinated with CCl4, it was completely recovered when treated with the more reactive CBrCl3. Subsequent investigations showed the latter result to be due to the poor acidity of 4 together with the rapid depletion of CBrCl3 and KOH by their reaction with each other, and led to a variety of other important results. 4-Hydroxyphenyl isopropyl sulfone (6) is unreactive with either CCl4 or CBrCl3 in KOH-t-BuOH, its phenoxide anion strongly reducing the electronegativity of the sulfonyl group, thereby inhibiting α-anion formation. This effect is reversed by the electron-withdrawing influence of two α-phenyls, so that benzhydryl 4-hydroxyphenyl sulfone (8) is readily α-halogenated in KOH-t-BuOH with CCl4 or CBrCl3. On further contact with KOH-t-BuOH the α-halogenated sulfones from 8 are decomposed into benzophenone and phenol. While the α-halogenated derivatives of 4-methoxyphenyl benzhydryl sulfone (9) are stable to base, they are decomposed even under mildly acidic conditions into 4-methoxyphenyl 4-methoxybenzenethiolsulfonate (9c), phenol, and benzophenone. Mono-α-halogenation of benzyl phenyl sulfone (10) enhances the rate of the subsequent halogenation, so that α,α-dihalogenation is attained while much substrate is still present and the mono-α-halogenated product is not detected. The ease of reductive debromination of α-bromo sulfones with Cl3C- was correlated with the stability of the formed α-anions, explaining the success with α-bromobenzylic sulfones but failure with α-bromoalkyl sulfones. In the presence of air and the absence of competing halogenation, formation of the α-anions of alkyl aryl sulfones is quickly accompanied by oxidative cleavage by atmospheric O2, leading to the formation of arenesulfonyl alcohols, arenesulfonyl halides, and haloarenes.