New tetrazoloquinolinyl methoxyphenyl-4-thiazolidinones: synthesis and antihyperglycemic evaluation

Abstract

We report synthesis and in vivo antihyperglycemic evaluation of new 3-substituted phenyl-2-(4-(tetrazolo[1,5-a]quinolin-4-ylmethoxy)phenyl)thiazolidin-4-ones (8a–l). The title 4-thiazolidinones were synthesized by one-pot cyclocondensation of new 4-(tetrazolo[1,5-a]quinolin-4-ylmethoxy)benzaldehyde (5), anilines, and mercaptoacetic acid in PEG-400. The required aldehyde (5) was also synthesized, starting from 2-chloroquinoline-3-carbaldehyde via a successive multistep route. The newly synthesized products were thoroughly characterized based on their spectral data. Amongst them, compounds 8a–g, j exhibited notable in vivo antihyperglycemic activity. Compounds 8f, g showed percentage improvement in oral glucose tolerance of 18.9 and 20.7, respectively, compared with 28.3 for the reference metformin.