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Mass spectrometry of 2‐substituted 5‐nitro‐2‐furyl thiazoles. Identification of microsomal nitroreduction products by electron impact mass spectrometry
Author(s) -
Mattammal Michael B.,
Zenser Terry V.,
Davis Bernard B.
Publication year - 1981
Publication title -
biomedical mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 121
eISSN - 1096-9888
pISSN - 0306-042X
DOI - 10.1002/bms.1200080705
Subject(s) - chemistry , thiazole , nitro , mass spectrometry , electron ionization , fragmentation (computing) , mass spectrum , chromatography , ion , medicinal chemistry , organic chemistry , alkyl , computer science , ionization , operating system
The electron impact mass spectral fragmentation of nitro heterocyclic carcinogens N ‐[4‐(5‐nitro‐2‐furyl)‐2‐thiazolyl]formamide, 2‐amino‐4‐(5‐nitro‐2‐furyl)thiazole, 2‐methyl‐4‐(5‐nitro‐2‐furyl)thiazole and 2‐methylamino‐4‐(5‐nitro‐2‐furyl)thiazole were studied. The molecular ions undergo two modes of cleavage: one giving [M–84] + ions which include the 2‐substituted thiazole ring, while the other gives rise to the fragment [M–74] + ions. The products of anaerobic microsomal nitroreduction of 2‐methyl‐4‐(5‐nitro‐2‐furyl)thiazole were isolated and purified by high‐pressure liquid chromatography. The metabolites undergo different fragmentation patterns compared to the parent nitro analogs. Metabolites from anaerobic enzymatic reduction showed identical gas chromatographic, high‐pressure liquid chromatographic and thin‐layer chromatographic properties to the chemically synthesized material. The metabolites were identified as 1‐(2‐methyl‐4‐thiazolyl)‐3‐cyano‐1‐propenone and 1‐(2‐methyl‐4‐thiazolyl)‐3‐cyano‐1‐propanone by mass spectral fragmentation pattern.