121626-40-2Relevant articles and documents
Synthesis and Oral Hypoglycemic Properties of 4-Oxo-4,5,6,7-tetrahydroindole-3-acetic Acids
Nagarajan, Kuppuswamy,Talwalker, Purnachard K.,Goud, A. Nagana,Shah, Rashmi K.,Shenoy, Sharada J.,Desai, Narasimha D.
, p. 1113 - 1123 (2007/10/02)
Condensation of β-acetyl-2-hydroxy-4,4-dimethyl-6-oxo-1-cyclohexene-1-propionic acid (8, R =R1 =Me) with ammonium acetate and primary amines affords tetrahydroindole-3-acetic acids (9), while another dimedone derivative 13 serves as starting material for isomeric indole-2-acetic acids (15). 4-Oxotetrahydroindole-2-carboxylic acids (77, 78) and 3-carboxylic acids (85, 86) are obtained from the corresponding benzofurans.Some of the 3-carboxylic acid esters are transformed to tricyclic compounds like 21-25.Good oral hypoglycemic activity in normal rats is shown generally by the 3-acetic acids among which C 8778-GO (3) and C 9001-GO (4) are most active.These two acids are also active in streptozotocin-induced diabetic rats and have been investigated extensively.Structure-activity relationships are discussed.