Studies on chemical carcinogens—XVII: Structure of carcinogenic 4-hydroxyaminoquinoline 1-oxide derivatives1

Add time:09/06/2019    Source:sciencedirect.com

Analysis of proton NMR spectra of N-methyl and O-acetyl derivatives of 4-hydroxyaminoquinoline 1-oxide (6) and 4-aminoquinoline 1-oxide revealed that the structure of carcinogenic 6 and its O-monoacetate are 1-hydroxy-4-hydroxyimino-1,4-dihydroquinoline and 1-hydroxy-4-acetoxyimino-1,4-dihydroquinoline, respectively, whereas 4-(N-methylhydroxyamino)quinoline 1-oxide, which is also carcinogenic, has a quinoline N-oxide structure, as have all the 4-amino derivatives examined. Since the structure of O-monoacetate of 6 was determined as such, it is assumed that aminoacyl derivative of 6, which is supposed to the ultimate carcinogenic form in its carcinogenesis, is formulated as 1-hydroxy-4-aminoacyloxyimino-1, 4-dihydroquinoline. PH-dependent UV spectral changes revealed that carcinogenic 6 and its N-methyl derivative are both acidic, the pKa being of similar value in both.

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