Cimoxatone

Cimoxatone
Clinical data
ATC code	none;
Identifiers
	IUPAC name 3-[[4-[5-(methoxymethyl)-2-oxo-oxazolidin-3-yl]phenoxy]methyl]benzonitrile;
CAS Number	73815-11-9 ;
PubChem CID	52542;
ChemSpider	47493 ;
UNII	V6FT1QJ7VL;
KEGG	D02581 ;
ChEMBL	ChEMBL2104092 ;
CompTox Dashboard (EPA)	DTXSID50868273 ;
ECHA InfoCard	100.070.537
Chemical and physical data
Formula	C19H18N2O4
Molar mass	338.363 g·mol−1
	InChI InChI=1S/C19H18N2O4/c1-23-13-18-11-21(19(22)25-18)16-5-7-17(8-6-16)24-12-15-4-2-3-14(9-15)10-20/h2-9,18H,11-13H2,1H3 ; Key:MVVJINIUPYKZHR-UHFFFAOYSA-N ;
	(what is this?) (verify)

Cimoxatone (MD 780515) is a reversible inhibitor of MAO-A (RIMA).^[1] It has a significant food interaction–related adverse effect in combination with tyramine.^[2] It was never marketed.

Synthesis

The condensation of 4-benzyloxyaniline [6373-46-2] (1) with 1-chloro-3-methoxy-2-propanol [4151-97-7] (2) in ethanol alcohol gave (3); cyclization with diethylcarbonate in toluene in the presence of NaOMe gave 5-(methoxymethyl)-3-(4-phenylmethoxyphenyl)-1,3-oxazolidin-2-one, CID:19781994 (4). Debenzylation gives 3-(4-hydroxyphenyl)-5-(methoxymethyl)-1,3-oxazolidin-2-one [135605-66-2] (5). which is alkylated with 3-cyanobenzyl bromide [28188-41-2] (6) to give cimoxatone (7).

References

^ Nair NP, Ahmed SK, Kin NM, West TE (1995). "Reversible and selective inhibitors of monoamine oxidase A in the treatment of depressed elderly patients". Acta Psychiatr Scand Suppl. 386: 28–35. doi:10.1111/j.1600-0447.1995.tb05921.x. PMID 7717092. S2CID 9100689.
^ Nair NP, Ahmed SK, Kin NM (November 1993). "Biochemistry and pharmacology of reversible inhibitors of MAO-A agents: focus on moclobemide". J Psychiatry Neurosci. 18 (5): 214–25. PMC 1188542. PMID 7905288.
^ Ancher, J.F.; Cimoxatone. Drugs Fut 1984, 9, 6, 412.
^ DE2923295 idem Guy R. Bourgery et al. U.S. patent 4,287,351 (1981 to Delalande S.A.). See for compound 200.

This drug article relating to the nervous system is a stub. You can help Wikipedia by expanding it.

[pmid7717092-1] Nair NP, Ahmed SK, Kin NM, West TE (1995). "Reversible and selective inhibitors of monoamine oxidase A in the treatment of depressed elderly patients". Acta Psychiatr Scand Suppl. 386: 28–35. doi:10.1111/j.1600-0447.1995.tb05921.x. PMID 7717092. S2CID 9100689.

[pmid7905288-2] Nair NP, Ahmed SK, Kin NM (November 1993). "Biochemistry and pharmacology of reversible inhibitors of MAO-A agents: focus on moclobemide". J Psychiatry Neurosci. 18 (5): 214–25. PMC 1188542. PMID 7905288.

[3] Ancher, J.F.; Cimoxatone. Drugs Fut 1984, 9, 6, 412.

[4] DE2923295 idem Guy R. Bourgery et al. U.S. patent 4,287,351 (1981 to Delalande S.A.). See for compound 200.

[1]

[2]

[3]

[4]

Synthesis

See also

References