121625-72-7

Basic information

• Product Name: 1-isobutyl-2,6,6-trimethyl-4-oxo-4,5,6,7-tetrahydro-3-indoleacetic acid
• Synonyms: 1-isobutyl-2,6,6-trimethyl-4-oxo-4,5,6,7-tetrahydro-3-indoleacetic acid
• CAS NO: 121625-72-7
• Molecular Formula: C17H25 N O3
• Molecular Weight: 0
• Mol File: 121625-72-7.mol

Chemical Properties

• Boiling Point: 471.1°Cat760mmHg
• Flash Point: 238.7°C
• Appearance: /
• Density: 1.15g/cm³
• Vapor Pressure: 1.11E-09mmHg at 25°C
• Refractive Index: 1.561
• CAS DataBase Reference: 1-isobutyl-2,6,6-trimethyl-4-oxo-4,5,6,7-tetrahydro-3-indoleacetic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 1-isobutyl-2,6,6-trimethyl-4-oxo-4,5,6,7-tetrahydro-3-indoleacetic acid(121625-72-7)
• EPA Substance Registry System: 1-isobutyl-2,6,6-trimethyl-4-oxo-4,5,6,7-tetrahydro-3-indoleacetic acid(121625-72-7)

Safety Data

• Hazardous Substances Data: 121625-72-7(Hazardous Substances Data)

Usage

InChI:InChI=1/C17H25NO3/c1-10(2)9-18-11(3)12(6-15(20)21)16-13(18)7-17(4,5)8-14(16)19/h10H,6-9H2,1-5H3,(H,20,21)

Upstream product

• 93647-07-5 β-acetyl-2-hydroxy-4,4-dimethyl-6-oxo-1-cyclohexene-1-propionic acid 
• 78-81-9 isobutylamine 
• 108-24-7 acetic anhydride 
• 126-81-8 dimedone 
• 110-16-7 maleic acid 

Relevant articles and documents

1-Isobutyl-2,6,6-trimethyl-4-oxo-4,5,6,7-tetrahydro-3-indoleacetic acid

The title compound (C17H25NO3) is a perhydro-indoleacetic acid which exhibits hypoglycemic activity. The cyclohexyl ring adopts a sofa conformation. The molecule contains an intramolecular O-H...O hydrogen bond.

Crystal and molecular structure of synthetic antidiabetic compound: Derivatives of tetrahydro indoles-(1 -N -butyl-2,6,6'-trimethyl-4-oxo-4,5,6,7-tetrahydro-3 indole acetic acid) and modeling studies

The crystal and molecular structure of (1-n-butyl-2,6,6'-trimethyl-4-oxo - 4,5,6,7 - tetrahydro - 3 indole acetic acid) with desirable anti hyperglycemic properties is reported. The title compound crystallises in orthorhombic space group Pbca with z =8. The unit cell dimensions are a=15.698(13)A, b= 11.639(2)A, c = 18.506(3)A, V =3381.2(29)A3, Dcal = 1.145Mg/m3. The cyclohexane ring adopts a sofa conformation. The structure is stabilized by C-H---O and O-H---O hydrogen bonds. Molecular modeling studies on this class of compounds and the classical antidiabetic agent tolbutamide reveal a structural basis for the similar biological activity exhibited by two totally structurally unrelated compounds.

Synthesis and oral hypoglycemic properties of two 4-oxo-4,5,6,7-tetrahydroindole-3-acetic acids

Condensation of β-acetyl-2-hydroxy-4,4-dimethyl-6-oxo-1- cyclohexene-1-propionic acid (3) with n-butyl and isobutylamines affords the title acids 4 and 5, respectively, which show good oral hypoglycemic activity in normal rats. Acids 4 and 5, are also active in streptozocin-induced diabetic rats. Results of extensive pharmacological and acute toxicity tests are reported.

Synthesis and Oral Hypoglycemic Properties of 4-Oxo-4,5,6,7-tetrahydroindole-3-acetic Acids

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.