Quinfamide

Quinfamide
Clinical data
Routes of; administration	Oral
ATC code	None;
Identifiers
	IUPAC name [1-(2,2-dichloroacetyl)-3,4-dihydro-2H-quinolin-6-yl] furan-2-carboxylate;
CAS Number	62265-68-3 ;
PubChem CID	71743;
ChemSpider	64787 ;
UNII	O1ZB1046R1;
CompTox Dashboard (EPA)	DTXSID90211320 ;
ECHA InfoCard	100.057.690
Chemical and physical data
Formula	C16H13Cl2NO4
Molar mass	354.18472 g/mol g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C1CC2=C(C=CC(=C2)OC(=O)C3=CC=CO3)N(C1)C(=O)C(Cl)Cl;
	InChI InChI=1S/C16H13Cl2NO4/c17-14(18)15(20)19-7-1-3-10-9-11(5-6-12(10)19)23-16(21)13-4-2-8-22-13/h2,4-6,8-9,14H,1,3,7H2 ; Key:SBJGFIXQRZOVTO-UHFFFAOYSA-N ;
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Quinfamide, is a drug that has anti-parasitic properties.^[1]

Synthesis

Quinfamide is one of a relatively small family of antiamoebic compounds containing a dichloroacetamide function.

The synthesis begins by amidation of 6-hydroxytetrahydroquinoline with dichloroacetyl chloride. The sequence is completed by acylation with 2-furoyl chloride.

References

^ Davila-Gutierrez, CE.; Vasquez, C.; Trujillo-Hernandez, B.; Huerta, M. (Mar 2002). "Nitazoxanide compared with quinfamide and mebendazole in the treatment of helminthic infections and intestinal protozoa in children". Am J Trop Med Hyg. 66 (3): 251–4. PMID 12139216.
^ D. M. Bailey, U.S. patent 3,997,542 (1976 to Sterling).
^ Bailey, Denis M.; Mount, Eldridge M.; Siggins, James; Carlson, John A.; Yarinsky, Allen; Slighter, Ralph G. (1979). "1-(Dichloroacetyl)-1,2,3,4-tetrahydro-6-quinolinol esters. New potent antiamebic agents". Journal of Medicinal Chemistry. 22 (5): 599. doi:10.1021/jm00191a031. PMID 458814.

[pmid12139216-1] Davila-Gutierrez, CE.; Vasquez, C.; Trujillo-Hernandez, B.; Huerta, M. (Mar 2002). "Nitazoxanide compared with quinfamide and mebendazole in the treatment of helminthic infections and intestinal protozoa in children". Am J Trop Med Hyg. 66 (3): 251–4. PMID 12139216.

[2] D. M. Bailey, U.S. patent 3,997,542 (1976 to Sterling).

[3] Bailey, Denis M.; Mount, Eldridge M.; Siggins, James; Carlson, John A.; Yarinsky, Allen; Slighter, Ralph G. (1979). "1-(Dichloroacetyl)-1,2,3,4-tetrahydro-6-quinolinol esters. New potent antiamebic agents". Journal of Medicinal Chemistry. 22 (5): 599. doi:10.1021/jm00191a031. PMID 458814.

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