Journal of Medicinal Chemistry p. 1245 - 1247 (1980)
Update date:2022-08-11
Topics:
Brundrett, Robert B.
A new product, ethylene glycol, was identified from BCNU <1,3-bis(2-chloroethyl)-1-nitrosourea> decomposition.The variation of ethylene glycol yield with pH indicates that there are two competing mechanisms of decomposition.At pH 7.4 the decomposition is predominantly through 2-chloroethyldiazohydroxide, and chloroethanol and acetaldehyde are the major products.At pH 5, the decomposition is predominantly through 4,5-dihydro-1,2,3-oxadiazole and 2-hydroxyethyldiazohydroxide, and ethylene glycol and acetaldehyde are the major products.Deuterium labeling shows that atboth pH's the acetaldehyde arises through a mechanism involving a hydride shift.At pH 5 in the presence of bromide, 2-bromoethanol is a major product and deuterium labeling shows that the hydroxyl is predominantly on the carbon which bore the chlorine in BCNU.
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