Floctafenine

Floctafenine is a nonsteroidal anti-inflammatory drug (NSAID).

Floctafenine

Clinical data
AHFS/Drugs.com	International Drug Names
ATC code	N02BG04 (WHO)
Identifiers
IUPAC name 2,3-Dihydroxypropyl 2-{[8-(trifluoromethyl)-4-quinolinyl]amino}benzoate
CAS Number	23779-99-9
PubChem CID	3360
DrugBank	DB08976^N
ChemSpider	3243
UNII	O04HVX6A9Q
CompTox Dashboard (EPA)	DTXSID8057695
ECHA InfoCard	100.041.696
Chemical and physical data
Formula	C20H17F3N2O4
Molar mass	406.361 g·mol^−1
3D model (JSmol)	Interactive image
SMILES FC(F)(F)c1cccc2c(ccnc12)Nc3ccccc3C(=O)OCC(O)CO
InChI InChI=1S/C20H17F3N2O4/c21-20(22,23)15-6-3-5-13-17(8-9-24-18(13)15)25-16-7-2-1-4-14(16)19(28)29-11-12(27)10-26/h1-9,12,26-27H,10-11H2,(H,24,25) Key:APQPGQGAWABJLN-UHFFFAOYSA-N

Synthesis

Flocatfenine synthesis: DE 1815467; eidem, U.S. Patent 3,644,368 Roussel Uclaf;[1]

The scheme involves first the conversion of ortho-trifluoromethyl aniline (1) to a quinolol. The compound is thus condensed with EMME (Ethoxy Methylene Malonic Diethyl Ester) and cyclized thermally (2). That intermediate is then saponified; the resulting acid is decarboxylated and finally converted to the 4-chloroquinoline (3) by reaction with phosphorus oxychloride. The displacement of chlorine with methyl anthranilate (4) then affords the coupled intermediate (5). An ester interchange of that product with glycerol leads to the glyceryl ester. There is thus obtained the NSAID floctafenine.

See also

• Glafenine, a chemically related NSAID

References

1. Mouzin, G.; Cousse, H.; Autin, J. M. (1980). "A New, Convenient Synthesis of Glafenine and Floctafenine". Synthesis. 1980: 54–55. doi:10.1055/s-1980-28923.