Studies on antianaphylactic agents. 6. Synthesis of some metabolites of 6-ethyl-3-(1H-tetrazol-5-yl)chromone and their analogs

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Abstract
The metabolites of 6-ethyl-3-(1H-tetrazol-5-yl)chromone (AA-344), an orally effective anti-allergic agent, and their analogs were synthesized to confirm the proposed structures and to determine their activity in the rat passive cutaneous anaphylaxis (PCA) test. A glucuronic acid metabolite was 1-deoxy-1-[5-(6-ethylchromon-3-yl)tetrazol-1-yl]-.beta.-D-glucopyranuronate. In 13C NMR spectra, the shift difference of the tetrazole ring carbons between a pair of isomers was more remarkable than that of the glycosidic carbons. The former is a useful criterion for distinguishing between such isomers. Some of the metabolites and analogs were active when administered i.v. and 2 metabolites were effective upon oral administration.

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