214401-46-4

Basic information

• Product Name: ethyl {7-[2-(4-cyanophenyl)ethyl]-1,2,3,4-tetrahydro-2-naphthalenyl}acetate
• Synonyms: ethyl {7-[2-(4-cyanophenyl)ethyl]-1,2,3,4-tetrahydro-2-naphthalenyl}acetate
• CAS NO: 214401-46-4
• Molecular Weight: 347.457
• Mol File: 214401-46-4.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: ethyl {7-[2-(4-cyanophenyl)ethyl]-1,2,3,4-tetrahydro-2-naphthalenyl}acetate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl {7-[2-(4-cyanophenyl)ethyl]-1,2,3,4-tetrahydro-2-naphthalenyl}acetate(214401-46-4)
• EPA Substance Registry System: ethyl {7-[2-(4-cyanophenyl)ethyl]-1,2,3,4-tetrahydro-2-naphthalenyl}acetate(214401-46-4)

Safety Data

• Hazardous Substances Data: 214401-46-4(Hazardous Substances Data)

Upstream product

• 60573-58-2 7-methoxy-3,4-dihydronaphthalene 
• 4133-34-0 7-methoxyl-2-tetralone 
• 32820-10-3 7-methoxy-1,2,3,4-tetrahydro-1-naphthol 
• 66107-32-2 4-cyanophenyl trifluoromethanesulfonate 
• 6836-19-7 7-Methoxy-1-tetralone 
• 3032-92-6 4-cyanophenylacetylene 
• 108972-18-5 (7-Methoxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-acetic acid ethyl ester 
• 767-00-0 4-cyanophenol 
• 75867-40-2 4-[2-(trimethylsilyl)ethynyl]benzonitrile 
• 63320-02-5 6-methoxy-1a,2,3,7b-tetrahydronaphtho[1,2-b]oxirene 
• 99318-10-2 ethyl 2-(7-methoxy-3,4-dihydro-naphthalen-2-yl)acetate 
• 214401-41-9 (7-hydroxy-1,2,3,4-tetrahydro-napthalen-2-yl)-acetic acid ethyl ester 
• 214401-44-2 (7-Trifluoromethanesulfonyloxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-acetic acid ethyl ester 

Relevant articles and documents

New platelet fibrinogen receptor glycoprotein IIb-IIIa antagonists: Orally active series of N-alkylated amidines with a 6,6-bicyclic template

The design, synthesis, and pharmacological evaluation of (S)-(-)-ethyl [6-[4-(morpholino-formimidoyl)benzamido]-3,4-dihydro-2H-1-benzopyran-3- yl]acetate hydrochloride ((S)-4·HCl, MS-180), an orally active glycoprotein IIb-IIIa (GPIIb-IIIa) antagonist, are reported. Pharmacophore mapping of amidino and carboxyl groups of already known GPIIb-IIIa antagonists led to the synthesis of nine amidino acids containing 6,6-bicyclic ring skeletons (10a-i). Among them, the compounds 10a,c,e having an amide bond and 1,2,3,4- tetrahydronaphthalene or 3,4-dihydro-2H-1-benzopyran skeleton showed marked inhibitions with IC50 values of 46-57 nM in human platelet aggregation assay in vitro, but low oral activities. N-Alkylation of the amidino group coupled with the ester prodrug approach afforded MS-180 ((S)-4·HCl), which generates in vivo the corresponding carboxylic acid (S)-3 as an active species. In vitro, (S)-3 inhibited ADP-induced aggregation of guinea pig, dog, and human platelets (IC50 = 110, 253, and 35 nM, respectively) and inhibited the binding of fibrinogen to immobilized GPIIb-IIIa of human platelets (IC50 = 0.12 nM). After oral administration of MS-180 ((S)4·HCl) to fasted beagle dog, ex vivo inhibition of platelet aggregation was observed. The maximal inhibitions were observed 2-4 h after dosing with dose dependency (60% inhibition at a dose of 1 mg/kg, 85% at 3 mg/kg, and 100% at 10 mg/kg, respectively) and the extent of the inhibitions paralleled the plasma concentration of the active species (S)-3. On the basis of these studies, we selected MS-180 ((S)-4·HCl) as a candidate for clinical evaluation as a drug for the treatment and prevention of thrombosis in patients.