187341-65-7Relevant articles and documents
Novel antidiabetic and hypolipidemic agents. 3. Benzofuran-containing thiazolidinediones
Reddy, K. Anji,Lohray,Bhushan,Bajji,Reddy, K. Vivekananda,Reddy, P. Rajamohan,Krishna, T. Hari,Rao, I. Nageswara,Jajoo, H. Kumar,Rao, N. V. S. Mamidi,Chakrabarti, Ranjan,Dileepkumar,Rajagopalan
, p. 1927 - 1940 (2007/10/03)
Several thiazolidinedione derivatives having 5-hydroxy-2,3-dihydro- 2,2,4,6,7-pentamethylbenzofuran moieties and their 5-benzyloxy derivatives and 5-hydroxy-2,4,6,7-tetramethylbenzofuran moieties were synthesized and evaluated in db/db mice. Insertion of an N-Me group into the linker between thiazolidinedione and substituted benzofuran pharmacophores showed considerable improvement in their euglycemic activity. Further improvement has been observed when a pyrrolidine moiety is introduced in the structure to give 5-[4-[N-[3(R/S)-5-benzyloxy-2,3-dihydro-2,2,4,6,7-pentamethylbenzofuran- 3-ylmethyl]-(2S)-pyrrolidin-2-ylmethoxy]phenylene]thiazolidine-2,4-dione (21a). At a 100 mg/kg/day dose of the maleate salt, compound 21a reduced the plasma glucose and triglyceride to the level of lean littermate, i.e. 8 ± 1 mM, and is the most potent and efficacious compound reported in this series.