389571-74-8

Basic information

• Product Name: (-)-3-(2-chlorophenyl)-6-cyano-1-(2-diethylaminoethyl)-(3R)-hydroxy-4-trifluoromethyloxindole
• Synonyms: (-)-3-(2-chlorophenyl)-6-cyano-1-(2-diethylaminoethyl)-(3R)-hydroxy-4-trifluoromethyloxindole
• CAS NO: 389571-74-8
• Molecular Weight: 451.876
• Mol File: 389571-74-8.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (-)-3-(2-chlorophenyl)-6-cyano-1-(2-diethylaminoethyl)-(3R)-hydroxy-4-trifluoromethyloxindole(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-3-(2-chlorophenyl)-6-cyano-1-(2-diethylaminoethyl)-(3R)-hydroxy-4-trifluoromethyloxindole(389571-74-8)
• EPA Substance Registry System: (-)-3-(2-chlorophenyl)-6-cyano-1-(2-diethylaminoethyl)-(3R)-hydroxy-4-trifluoromethyloxindole(389571-74-8)

Safety Data

• Hazardous Substances Data: 389571-74-8(Hazardous Substances Data)

Upstream product

• 259667-88-4 3-(2-chlorophenyl)-1-(2-diethylaminoethyl)-3(R)-hydroxy-6-iodo-4-trifluoromethyloxindole 
• 98-46-4 3-trifluoromethylnitrobenzene 
• 41253-01-4 1-iodo-3-nitro-5-(trifluoromethyl)benzene 
• 389571-69-1 3-iodo-5-trifluoromethylaniline 
• 259667-63-5 1-(2-diethylaminoethyl)-6-iodo-4-trifluoromethylisatin 

Relevant articles and documents

Oxindole derivatives as orally active potent growth hormone secretagogues

A series of substituted oxindole derivatives was synthesized and evaluated for growth hormone (GH) releasing activity using cultured rat pituitary cells. (+)-6-Carbamoyl-3-(2-chlorophenyl)-(2-diethylaminoethyl)- 4-trifluoromethyloxindole (SM-130686, 37S) was found to have potent activity (EC50 = 3.0 nM), while the other enantiomer 37R had reduced activity. The absolute configuration of 37S was confirmed by X-ray crystallographic analysis. Compound 37S showed a good pharmacokinetic profile in rats with 28% oral bioavailability at 10 mg/kg and excellent in vivo activity as evidenced by a significant weight gain after 4 days of oral administration at 10 mg/kg twice a day. Compound 37S displaced the binding of 35S-MK-677 to human GHS-R with an IC50 value of 1.2 ± 0.2 nM.