3-Phenylpropyl carbamate

Btich investigated the activities, following intraperitoneal injection, of a series Of 3-phenylpropyl carbamate derivatives on formalin, dextran and... 

Representative procedure synthesis of t-butyl (3-phenylpropyl)carbamate ... 

Biich investigated the activities, following intraperitoneal injection, of a series of 3-phenylpropyl carbamate derivatives on formalin, dextran and 5-hydroxytryptamine oedema in the rat-paw. All compounds showed antiinflammatory activity and all apart from one were more active than meprobamate. Further experiments demonstrated that one of these, 3-phenylpropyl carbamate itself (phenprobamate, proformiphen, Gamaquil, MH 532), Ph(CH2)8-0 CO-NHg, a central muscle relaxant with analgesic and antipyretic properties, possesses anti-inflammatory effects comparable to those of phenylbutazone . In doses of 160 mg/kg orally, this compound does not delay the appearance of ultra-violet erythema in the guinea-pig. 

Y-PHENYLPROPYL CARBAMATE see PGA750 3-PHENYL-N-(4-PROPYLCYCLOHEXYL)-2-PROPENAMIDE see PGB850... 

PHENYLPROPYL PROPIONATE see HHQ550 P-PHENYLPROPYL PROPIONATE see HHQ550 1-PHENYL-2-PROPYNYL CARBAMATE see PGEOOO a-(l-PHENYL-lH-PYRAZOL-4-YL)-l-PIPERIDINEBUTANOL see PGE550 l-PHENYL-l-(2-PYRIDYL)-3-DIMETHYLAADNOPROPANE see TMJ750 l-PHENYL-l-(2-PYRIDYL)-3-... 

The results uncovered by Muller have been corroborated by the subsequent studies from the Du Bois group, particularly with respect to the intramolecular reaction. The stereospecific C(sp )—H insertion of the carbamate-derived nitrene depicted in Scheme 6A was the first relevant reaction in favor of the asynchronous concerted addition.More significantly, the extensive analysis of the rhodium-catalyzed intramolecular C(sp )-H amination of sulfamates has led to the same conclusion. The Hammett analysis (/0= —0.55 vs. and the kinetic isotope effect observed from the monodeuterated phenylpropyl sulfamate 9 (KIE = 2.6 0.2) clearly argue in favor of this mechanistic scenario (Scheme 17). Additionally, the reaction from the cyclopropyl radical clock 12 supports this hypothesis by furnishing a single product isolated with an excellent yield of 91%. 

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