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Demethylation reactions of 4‐amino‐ N ‐(2,6‐dimethoxy‐4‐pyrimidinyl)benzenesulfonamide (sulfadimethoxine) in strongly basic aqueous solution
Author(s) -
Miura Tadayoshi,
Ono Makoto,
Yoshida Atomi,
Kato Masahiro,
Yoshioka Toshiyuki,
Tachi Hiroshi,
Eguchi Shoji
Publication year - 1994
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570310618
Subject(s) - chemistry , demethylation , sulfadimethoxine , hydrolysis , aqueous solution , reactivity (psychology) , medicinal chemistry , sulfonamide , organic chemistry , stereochemistry , chromatography , biochemistry , alternative medicine , medicine , gene expression , pathology , dna methylation , gene
Hydrolysis of 1 in strongly basic aqueous solution afforded mono‐ and didemethylated products 2,3 and 4 , that are postulated as the metabolites of 1 in some animals. This hydrolytic demethylation was shown to proceed stepwise via mono‐demethylation to give 2 and 3 , followed by their further demethylation to 4 . The hydrolytic reactivity of 1–3 was rationalized based on MO calculation results and 13 C nmr data.