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  N
PubChem CID	71743
ChemSpider	64787  N
UNII	O1ZB1046R1
KEGG	D00641
CompTox Dashboard (EPA)	DTXSID90211320
ECHA InfoCard	100.057.690
Chemical and physical data
Formula	C16H13Cl2NO4
Molar mass	354.18 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 N Key:SBJGFIXQRZOVTO-UHFFFAOYSA-N N
NY  (what is this?)    (verify)

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.^{[ citation needed ]}

Quinfamide synthesis:

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

References

1. Davila-Gutierrez CE, Vasquez C, Trujillo-Hernandez B, Huerta M (March 2002). "Nitazoxanide compared with quinfamide and mebendazole in the treatment of helminthic infections and intestinal protozoa in children". The American Journal of Tropical Medicine and Hygiene. 66 (3): 251–4. doi: 10.4269/ajtmh.2002.66.251 . PMID   12139216.
2. US 3997542,Bailey, Denis Mahlon,"1-(Halogenated-acetyl)-1,2,3,4-tetrahydro-6-quinolinols and esters thereof",published 1976-12-14, assigned to Sterling Drug Inc.  
3. Bailey DM, Mount EM, Siggins J, Carlson JA, Yarinsky A, Slighter RG (May 1979). "1-(Dichloroacetyl)-1,2,3,4-tetrahydro-6-quinolinol esters. New potent antiamebic agents". Journal of Medicinal Chemistry. 22 (5): 599–601. doi:10.1021/jm00191a031. PMID   458814.