A series of 5-(naphthalenylsulfony1)-2, 4-thiazolidinediones were synthesized and evaluated for antihyperglycemic activity in an insulin-resistant, genetically diabetic db/db mouse model of non-insulin-dependent diabetes mellitus (NIDDM). The sulfones could be synthesized by a novel, selective C-5 sulfonylation of dilithio-2, 4-thiazolidinedione with appropriate sulfonyl chlorides. Within this series, naphthalene was found to be superior to ...