quinfamide
{{Short description|Chemical compound with anti-parasitic properties}}
{{Drugbox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 470603052
| IUPAC_name = [1-(2,2-dichloroacetyl)-3,4-dihydro-2H-quinolin-6-yl] furan-2-carboxylate
| image = Quinfamide.svg
| width = 170
| tradename =
| pregnancy_AU =
| pregnancy_US =
| pregnancy_category =
| legal_AU =
| legal_CA =
| legal_UK =
| legal_US =
| legal_status =
| routes_of_administration = Oral
| bioavailability =
| protein_bound =
| metabolism =
| elimination_half-life =
| excretion =
| CAS_number_Ref = {{cascite|changed|??}}
| ATC_prefix = None
| ATC_suffix =
| CAS_number = 62265-68-3
| PubChem = 71743
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 64787
| smiles = C1CC2=C(C=CC(=C2)OC(=O)C3=CC=CO3)N(C1)C(=O)C(Cl)Cl
| StdInChI = 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
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = SBJGFIXQRZOVTO-UHFFFAOYSA-N
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = O1ZB1046R1
| KEGG = D00641
| C=16 | H=13 | Cl=2 | N=1 | O=4
| melting_point =
| melting_high =
}}
Quinfamide is a drug that has anti-parasitic properties.{{cite journal | vauthors = Davila-Gutierrez CE, Vasquez C, Trujillo-Hernandez B, Huerta M | title = Nitazoxanide compared with quinfamide and mebendazole in the treatment of helminthic infections and intestinal protozoa in children | journal = The American Journal of Tropical Medicine and Hygiene | volume = 66 | issue = 3 | pages = 251–4 | date = March 2002 | pmid = 12139216 | doi = 10.4269/ajtmh.2002.66.251 | doi-access = free }}
Synthesis
Quinfamide is one of a relatively small family of antiamoebic compounds containing a dichloroacetamide function.{{cn|date=December 2022}}
File:Quinfamide synthesis.svg|title=1-(Halogenated-acetyl)-1,2,3,4-tetrahydro-6-quinolinols and esters thereof|inventor1-last=Bailey|inventor1-first=Denis Mahlon}}{{cite journal | vauthors = Bailey DM, Mount EM, Siggins J, Carlson JA, Yarinsky A, Slighter RG | title = 1-(Dichloroacetyl)-1,2,3,4-tetrahydro-6-quinolinol esters. New potent antiamebic agents | journal = Journal of Medicinal Chemistry | volume = 22 | issue = 5 | pages = 599–601 | date = May 1979 | pmid = 458814 | doi = 10.1021/jm00191a031 }}]]
The synthesis begins by amidation of 6-hydroxytetrahydroquinoline with dichloroacetyl chloride. The sequence is completed by acylation with 2-furoyl chloride.