Design, synthesis, and biological evaluation of substituted-N-(thieno[2,3-b]pyridin-3-yl)-guanidines, N-(1H-pyrrolo[2,3-b]pyridin-3-yl)-guanidines, and N-(1H-indol-3-yl)-guanidines

Bioorganic & Medicinal Chemistry
2007.0

Abstract

Sulfonylureas stimulate insulin secretion independent of the blood glucose concentration and therefore cause hypoglycemia in type 2 diabetic patients. Over the last years, a number of aryl-imidazoline derivatives have been identified that stimulate insulin secretion in a glucose-dependent manner. In the present study, we have developed three series of substituted N-(thieno[2,3-b]pyridin-3-yl)-guanidine (2a-l), N-(1H-pyrrolo[2,3-b]pyridin-3-yl)-guanidine (3a-l), and N-(1H-indol-3-yl)-guanidine (4a-l) as new class of antidiabetic agents. In vitro glucose-dependent insulinotropic activity of test compounds 2a-l, 3a-l, and 4a-l was evaluated using RIN5F (Rat Insulinoma cell) based assay. All the test compounds showed concentration-dependent insulin secretion, only in presence of glucose load (16.7mmol). Some of the test compounds (2c, 3c, and 4c) from each series were found to be equipotent to BL 11282 (standard aryl-imidazoline), which indicated that the guanidine group acts as a bioisostere of imidazoline ring system.

Knowledge Graph

Similar Paper

Design, synthesis, and biological evaluation of substituted-N-(thieno[2,3-b]pyridin-3-yl)-guanidines, N-(1H-pyrrolo[2,3-b]pyridin-3-yl)-guanidines, and N-(1H-indol-3-yl)-guanidines
Bioorganic & Medicinal Chemistry 2007.0
Synthesis and antidiabetic activity of 2,5-disubstituted-3-imidazol-2-yl-pyrrolo[2,3-b]pyridines and thieno[2,3-b]pyridines
Bioorganic & Medicinal Chemistry 2007.0
Preparation and antidiabetic activity of some sulfonylurea derivatives of 3,5-disubstituted pyrazoles
Journal of Medicinal Chemistry 1979.0
Novel sulfonyl(thio)urea derivatives act efficiently both as insulin secretagogues and as insulinomimetic compounds
European Journal of Medicinal Chemistry 2014.0
Molecular Design, Synthesis, and Hypoglycemic Activity of a Series of Thiazolidine-2,4-diones
Journal of Medicinal Chemistry 2000.0
Synthesis of 3,8,9-trisubstituted-1,7,9-triaza-fluorene-6-carboxylic acid derivatives as a new class of insulin secretagogues☆
Bioorganic & Medicinal Chemistry 2007.0
Construction of phenoxazine rings containing nitro and sulfonic acid groups leading to phenoxazine-3-sulfonamide derivatives: their evaluation as novel and potential insulin secretagogues
MedChemComm 2014.0
Synthesis, characterization, hypoglycemic and aldose reductase inhibition activity of arylsulfonylspiro[fluorene-9,5′-imidazolidine]-2′,4′-diones
European Journal of Medicinal Chemistry 2015.0
Novel 5-(3-Aryl-2-propynyl)-5-(arylsulfonyl)thiazolidine-2,4-diones as Antihyperglycemic Agents
Journal of Medicinal Chemistry 1998.0
Synthesis and antihyperglycemic evaluation of new 2,4-thiazolidinediones having biodynamic aryl sulfonylurea moieties
Bioorganic & Medicinal Chemistry Letters 2012.0