63320-02-5

Basic information

• Product Name: 6-METHOXY-1A,2,3,7B-TETRAHYDRO-1-OXA-CYCLOPROPA[A]NAPHTHALENE
• Synonyms: 6-METHOXY-1A,2,3,7B-TETRAHYDRO-1-OXA-CYCLOPROPA[A]NAPHTHALENE
• CAS NO: 63320-02-5
• Molecular Formula: C₁₁H₁₂O₂
• Molecular Weight: 176.21178
• Mol File: 63320-02-5.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 6-METHOXY-1A,2,3,7B-TETRAHYDRO-1-OXA-CYCLOPROPA[A]NAPHTHALENE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-METHOXY-1A,2,3,7B-TETRAHYDRO-1-OXA-CYCLOPROPA[A]NAPHTHALENE(63320-02-5)
• EPA Substance Registry System: 6-METHOXY-1A,2,3,7B-TETRAHYDRO-1-OXA-CYCLOPROPA[A]NAPHTHALENE(63320-02-5)

Safety Data

• Hazardous Substances Data: 63320-02-5(Hazardous Substances Data)

Upstream product

• 60573-58-2 7-methoxy-3,4-dihydronaphthalene 
• 32820-10-3 7-methoxy-1,2,3,4-tetrahydro-1-naphthol 
• 6836-19-7 7-Methoxy-1-tetralone 
• 886040-06-8 2-bromo-7-methoxy-1,2,3,4-tetrahydronaphthalen-1-ol 

Downstream Products

• 4133-34-0 7-methoxyl-2-tetralone 
• 214401-43-1 [7-(4-Cyano-benzyloxy)-naphthalen-2-yl]-acetic acid ethyl ester 
• 214401-46-4 ethyl {7-[2-(4-cyanophenyl)ethyl]-1,2,3,4-tetrahydro-2-naphthalenyl}acetate 
• 214401-42-0 [7-(4-Cyano-benzyloxy)-1,2,3,4-tetrahydro-naphthalen-2-yl]-acetic acid ethyl ester 

Relevant articles and documents

Piperazine compounds

A compound selected from those of formula (I): wherein: R1, R2, R3 and R4, which may be the same or different, each represent an atom or group selected from hydrogen, halogen, alkyl, alkoxy, phenyl and cyano, X represents a bond, an oxygen atom or a group selected from —(CH2)m—, —OCH2— and —NR5—, wherein m represents 1 or 2, and R5 is as defined in the description, Y represents an oxygen atom or a group selected from NR7 and CHR8, wherein R7 and R8 are as defined in the description, Z represents a nitrogen atom or a CH group, n represents 1 or 2, Ak represents an alkylene chain, Ar represents an aryl or heteroaryl group, its optical isomers, and addition salts thereof with a pharmaceutically acceptable acid. Medical products containing the same which are useful in the treatment of conditions requiring a serotonin reuptake inhibitor and/or NK1 antagonist.

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.