4-Phenoxyphenyl sulfone

M,Al -[2,2-(4-Phenoxyphenyl) hexafluoroisopropylidene]bis-(4-phenylethynyl-phthalimide), 487 4-Phenoxyphenyl sulfone, 249 4-Phenoxy-2,3,5,6-tetrafluorobenzonitrile, 284, 293 Phenyl benzoate, 223 1-Phenyldecane, 223 Al-Phenyl-4,5-dichlorophthalimide, 189... 

The electrophilic polymerization of this type is often referred to as Friedel-Crafts polymerization. Examples are polymers obtained from near equimolar feeds of terephthalic acid as dicarboxylic acid and 4-phenoxyphenyl sulfone, or 4-biphenylyl sulfone, respectively. Usage of 4,4 -diphenoxybenzophenone yields a poly (ketone). 

A series of phenoxyphenyl sulfone A-formylhydroxy-lamines was identified that contained potent and selective matrix metalloproteinase (MMP) inhibitors. Compound 27 displayed remarkable selectivity for both MMP-2 and MMP-9 over the undesired MMP-1. Unfortunately, 27 had no oral bioavailability. SAR modifications revealed that diol 28 maintained ideal selectivity, but suffered from low plasma exposure in monkey and a short in vivo half-life. Further modification showed that acetonide 29 had the desired selectivity for MMP-2 and MMP-9 and also displayed an optimal PK profile in monkeys with a plasma concentration 18-fold higher than 28. Oral bioavailabilities for 29 were >70% in rat, dog, and monkey. 

Wada, C. K., Holms, J. H., Curtin, M. L. et al. Phenoxyphenyl sulfone 7V-formylhydroxylamines (retrohydroxamates) as potent, selective, orally bioavailable matrix metalloproteinase inhibitors. J. Med. Chem. 2002, 45, 219-232. 

Bis(3,4-dicarboxyl-phenoxy)benzene dianhydride, 477 4,4 -Bis(3,4-dicarboxyl phenoxyphenyl)-isopropylidene dianhydride, 476, 477 4,4 -Bis(2,3-dicarboxyphenoxy)diphenyl sulfone dianhydride, 489 4,4 -Bis(3,4-dicarboxyphenoxy)diphenyl sulfone dianhydride, 489... 

Compound CXII has been prepared by Nardi et al. [288] and reported to be more active than the biphenylyl-substituted acids liosol (LXXVII) and desenovis (LXXXI). The mesyl derivative, -phenoxyphenyl methane-sulfonate, Upjohn-22,105 (CXIII), has been found to possess hypocholesterolemic activity at 10 mg/kg and predominantly triglyceride-lowering activity at 5 mg/kg in the triton-induced hyperlipemic rat. This substance also elicited hepatotrophic activity [289]. Similarly, the basic ester, Sandoz 42-348 (CXIV) has also been reported to produce hepatomegaly in rats, and is considered more active than clofibrate as a hypolipidemic agent in the rat [290]. Compound CXIV has been reported to differ from clofibrate in its mode of action in that it significantly accelerated the oxidation of cholesterol-26-C to C Og and markedly increased bile-acid secretion in the male rat [291]. Compound CXIV at a daily dose of... 

A new monomer (4-(4 -trifluoromethyl)phenoxyphenyl)hydro-quinone (TFPOPH) was synthesized in a three-step synthesis. A series of poly (aryl ether ketone) copolymers were prepared by the reaction of (4-(4 -trifluoromethyl)phenoxyphenyl) hydroquinone and hydroquinone (HQ) with 4,4 -difluorobenzophenone (Dre) in the presence of potassium carbonate. A typical polymerization was carried out as follows To a three-neck round bottom flask were added hydroquinone and (4-(4 -trifluoromethyl)-phenox)q henyl) hydroquinone (TFPOPH) (total O.lOmol) in molar ratios of 100 0, 80 20, 60 40, 40 60, 20 80 and 0 100, 4,4 -difluorobenzophenone (DFB), toluene and 3.04 g (0.022 mol) of potassium carbonate and tetramethylene sulfone (TMS) (a prescribed amount shown in Table 10.5) and heated to 140°C to remove produced water by azeotropic distillation with toluene and then rose up to 210°C for 4-6 h. The copolymer was precipitated by pouring the hot reaction mixture into a large amount of distilled water, filtered, and washed... 

The relevance of these products was demonstrated via the three-step preparation of a potential MMP-2/-9 inhibitor 199 [81]. 3-Sultam 196 was initially reduced to chloromethyl derivative 197 and then ring-opened with (4-phenoxyphenyl) magnesium bromide to give sulfone 198. Subsequent intramolecular nucleophilic substitution gave the desired aziridine 199 in 64% overall yield with no loss of enantiopurity (Scheme 3.45). 

---