Demethylation reactions of 4‐amino‐ N ‐(2,6‐dimethoxy‐4‐pyrimidinyl)benzenesulfonamide (sulfadimethoxine) in strongly basic aqueous solution | Zendy

Miura Tadayoshi | Zendy; Ono Makoto | Zendy; Yoshida Atomi | Zendy; Kato Masahiro | Zendy; Yoshioka Toshiyuki | Zendy; Tachi Hiroshi | Zendy; Eguchi Shoji | Zendy

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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.

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