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A series of naphthalenyl 3H-1,2,3,5-oxathiadiazole 2-oxides was prepared and tested for antihyperglycemic activity in the db/db mouse, a model for type 2 (non-insulin dependent) diabetes mellitus. Substitution at the 1-, 5-, or 8-positions of the naphthalene ring with a halogen was found to be beneficial to antihyperglycemic activity. 4-[(5-Chloronaphthalen-2-yl)methyl]-3H-1,2,3,5-oxathiadiazole++ + 2-oxide (45), one of the most potent compounds in this series, was selected for further pharmacological evaluation.


J W Ellingboe, L J Lombardo, T R Alessi, T T Nguyen, F Guzzo, C J Guinosso, J Bullington, E N Browne, J F Bagli, J Wrenn. Antihyperglycemic activity of novel naphthalenyl 3H-1,2,3,5-oxathiadiazole 2-oxides. Journal of medicinal chemistry. 1993 Aug 20;36(17):2485-93

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PMID: 8355249

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