Some Analogs of Chlordiazepoxide

Bae, Sang Cheol; Gochman, Carl; Sj, Childress

doi:10.1021/jm01236a008

Cited by 18 publications

(1 citation statement)

References 6 publications

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“…In accordance with the study of the reaction of simple sulphur or sulphydryl containing compounds with oxaziridines (SLAC~ and WATSON I973), it seems plausible that in the reaction with glutathione the 4,5-bond of n is involved. The latter compound has sedative, muscle-relaxing or anticonvulsive properties (NING and MADAN /976 ) and showed a biological activity approaching that of chlordiazepoxide (BELL et al 1962b). ppm ary support for the study of photochemical processes in vivo, which are shown to be of importance in relation to human health (HENDERSON and JENKS I979).…”

Section: Identification Of the Conjugatementioning

confidence: 99%

Photochemical decomposition of 1,4-benzodiazepines

Cornelissen

Henegouwen

1980

Pharmaceutisch Weekblad Scientific Edition

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By labelling chlordiazepoxide and diazepam with t4C it was possible to follow quantitatively the photochemical decomposition of these compounds. It was found for chlordiazepoxide that the wavelength of light does not determine the character, but only the concentrations of the products formed.On irradiation of chlordiazepoxide, dissolved in methanol or methanol-water (pH=7.4), an oxaziridine is formed, which is subsequently converted into a quinoxaline and a benzoxadiazocine derivative. However, by irradiation in the presence of glutathione, the rate of decomposition is increased and the scheme is completely changed. Instead of the quinoxaline and the benzoxadiazocine derivative, the reduced form ofchlordiazepoxide and a conjugate are formed. It was established that the oxaziridine, the first photoproduct of chlordiazepoxide, reacts spontaneously with glutathione at room temperature without light.On irradiation of diazepam, dissolved in methanolwater (pH=7.4), with light of 300 nm a benzophenone derivative is the only decomposition product, while with light of 254 nm also a quinazoline derivative is formed as a minor product. With methanol as solvent (2 =254 nm) the concentration of the products formed is strongly influenced, quinazoline derivatives become the main products and the benzophenone derivative a minor product. (Pharm. Weekblad Sci. Ed. 2,(39)(40)(41)(42)(43)(44)(45)(46)(47)(48).

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Section: Identification Of the Conjugatementioning

confidence: 99%