Phenoxy analogs

The halogen displacement polymerization proceeds by a combination of the redistribution steps described for oxidative coupling polymerization and a sequence in which a phenoxide ion couples with a phenoxy radical (eq. 11) and then expels a bromide ion. The resultant phenoxy radical can couple with another phenoxide in a manner that is analogous to equation 11 or it can redistribute with other aryloxy radicals in a process analogous to equations 7 and 8. 

Analog reagieren (2-Nitro-phenoxy)-, (2-Nitro-phenylthio)-essigsauren bzw. 3-Oxo-3-(2-nitro-phenyl)-propansauren2 ... 

An early biphenyl candidate, A-331440 (6) has been reported to be a competitive, potent inverse agonist with balanced activity at human and rat H3Rs with good oral bioavailability [40]. While A-331440 was active in obesity models, its development was precluded by genotoxicity issues [41], The latter was eliminated by a tactical orf/zo-substitution on the phenoxy central core by fluorine to provide A-417022 (7). A-417022 and the 3,5-difluoro analog (A-423579) also produced prolonged weight loss over a 28-day period in a rat diet-induced obesity model [17,41],... 

Chloro(phenylthio)carbene [32] has been produced by the standard phase-transfer catalytic procedure from PhSCHCK and trapped by alkenes (see Section 7.3), although the carbene is also prone to dimerization to give [PhS(Cl)C=C(Cl)SPhj. In a similar manner, phenylthiocarbene has been obtained from PhSCH2Cl [33] and chloro(phenoxy)carbene from dichloro(phenoxy)methane [34]. Reaction of the analogous seleno derivatives produce the conesponding phenylselenocarbenes... 

Metoprolol Metoprolol, l-(wo-propylamino)-3-[4 (2-methoxyethyl)phenoxy]-2-propanol (12.1.5), is synthesized by reacting 4-(2-methoxyethyl)phenol with epichlorhy-dride in the presence of a base, isolating l,2-epoxy-3-[4 (2-methoxyethyl)phenoxy] propane (12.1.4), the subsequent reaction of which, analogous to that described before, with jio-propylamine, gives an opening of the epoxide ring and leads to the formation of metoprolol (12.1.5) [7,8]. 

Drugs of this series include clofibrate and gemfibrozil, which are derivatives of phenoxy-carboxylic acids—fibrates probucol, which is a substituted fc/y-mercaptophenol and also natural compounds lovastatin, mevastatin, and their analogs. They will be examined separately because it is difficult to explain their action via the entire mechanism. 

In the course of their studies on the synthesis of ot-amido-spiro-(5-lactams as analogs of penicillin and cephalosporin, Manhas et al. [76] have prepared 1-phenyl-3-phenoxy-4,4-spirocyclohexylazetidin-2-ones by the reaction of phenoxyacetyl chloride 7 and cyclohexylidenephenylamine 8 in the presence of triethylamine and dichloromethane. Azidoacetyl chloride was found to be even more reactive... 

Analog wird z. B. 2,2-Bis-[4-nitro-phenoxy]-4,6-bis-[trifluormethyl]-l,3,5,2-triazaphosphorin (54% Schmp. 94-96°) erhallen2 1 ... 

Photochromic transformations that are similar to these of the above anthraqui-nones are also characteristic for anthrapyridones and anthrapyridines. The character of spectral changes (Table 7.5) and the similarity of photochromic transformations to the conversion processes for the acyl derivatives of 1-phenoxy-4-aminoanthraquinone suggest an analogous mechanism for 6-phcnoxy-A-methy-lanthrapyridone (IIB1) (Scheme 17).37 Anthrapyridones of another type (IIB2) show similar photochromic properties. 

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