259667-84-0

Upstream product

• 36692-27-0 2-chlorophenylmagnesium bromide 
• 259667-63-5 1-(2-diethylaminoethyl)-6-iodo-4-trifluoromethylisatin 
• 89479-33-4 2-chlorophenylmagnesium iodide 
• 98-46-4 3-trifluoromethylnitrobenzene 
• 389571-69-1 3-iodo-5-trifluoromethylaniline 
• 41253-01-4 1-iodo-3-nitro-5-(trifluoromethyl)benzene 

Downstream Products

• 259667-93-1 3-(2-chlorophenyl)-6-cyano-1-(2-diethylaminoethyl)-3-hydroxy-4-trifluoromethyloxindole 
• 850442-33-0 (+)-1-(2-Diethylaminoethyl)-4-trifluoromethyl-6-[4-(N-hydroxyethylcarbamoyl)-1-butynyl]-3-hydroxy-3-(2-chlorophenyl)oxindole 
• 259666-72-3 (+)-1-(2-Diethylaminoethyl)-4-trifluoromethyl-6-(3-methanesulfonylamino-1-propynyl)-3-hydroxy-3-(2-chlorophenyl)oxindole 

Relevant academic research and scientific papers

Oxindole derivative

An oxindole of Formula 1 or a prodrug thereof, or a pharmaceutically acceptable salt thereof is useful for growth hormone releaser: wherein R1, R2, R3and R4are independently hydrogen, optionally substituted alkyl etc; R5is optionally substituted aryl or optionally substituted heteroaryl; Z is —O— or —NH—; one of W1and W2is hydrogen, alkyl or —Y—CON(R10)R11; the other of W1and W2is n is 1, 2 or 3; m is 0, 1, 2 or 3; Y is single bond or C1-C3alkylene; R6and R7are independently hydrogen, optionally substituted alkyl etc; R8and R9are independently hydrogen, optionally substituted alkyl etc; R10and R11are independently hydrogen, alkyl etc.

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.