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153420-96-3

153420-96-3 Structure

153420-96-3 Structure
IdentificationBack Directory
[Name]

Atibeprone
[CAS]

153420-96-3
[Synonyms]

Atibeprone
2H-1-Benzopyran-2-one, 3,4-dimethyl-7-[[5-(1-methylethyl)-1,3,4-thiadiazol-2-yl]methoxy]-
[Molecular Formula]

C17H18N2O3S
[MDL Number]

MFCD00866584
[MOL File]

153420-96-3.mol
[Molecular Weight]

330.4
Hazard InformationBack Directory
[Originator]

Atibeprone,BASF
[Uses]

Atibeprone (Lu 53439) is a selective MAO-B inhibitor. Atibeprone has antidepressant activity[1][2].
[Manufacturing Process]

10 mmol of 7-methoxy-3,4-dimethylcoumarin were stirred with 10 mmol (4.04 g) of Lawesson's reagent (2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4- diphosphetane 2,4-disulfide) in 20 ml of toluene at 90°C for 1-2.5 h. After cooling, the solvent was distilled off, the residue was taken up in DMF, and water was added. The precipitate was filtered off with suction and the crude 3,4-dimethyl-7-(2-isopropyl-1,3,4-thiadiazol-5-ylmethoxy)-2-thiocoumarin was purified by recrystallization from methanol or by column chromatography (silica gel, methylene chloride). Yield: 98%, melting point: 134-135°C.
[Therapeutic Function]

Antidepressant
[References]

[1] L?scher W,et al. Inhibition of monoamine oxidase type A, but not type B, is an effective means of inducing anticonvulsant activity in the kindling model of epilepsy. J Pharmacol Exp Ther. 1999 Mar;288(3):984-92. PMID:10027835
[2] Chhajed M, et al. Synthesis of 5-arylidine amino-1,3,4-thiadiazol-2-[(N-substituted benzyol)]sulphonamides endowed with potent antioxidants and anticancer activity induces growth inhibition in HEK293, BT474 and NCI-H226 cells. Med Chem Res. 2014;23(6):3049-3064. DOI:10.1007/s00044-013-0890-z
Spectrum DetailBack Directory
[Spectrum Detail]

Atibeprone(153420-96-3)1HNMR
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