Nifurquinazol

Nifurquinazol

Systematic (IUPAC) name
2,2'-{[2-(5-nitrofuran-2-yl)quinazolin-4-yl]imino}diethanol
Clinical data
Routes of administration	?
Legal status	Uncontrolled
Identifiers
CAS Number	5055-20-9
ATC code	None
PubChem	CID 21139
ChemSpider	19878
UNII	44E5RRL600
KEGG	D05164
Chemical data
Formula	C16H16N4O5
Molar mass	344.32 g/mol
SMILES O=[N+]([O-])c3oc(c1nc(N(CCO)CCO)c2c(n1)cccc2)cc3

Nifurquinazol (NF-1088) is an antibacterial agent of the nitrofuran class.^[1] It was never marketed.^[1]

Synthesis

Nifurquinazol synthesis:^[2][3]

Treatment of the amide from 5-nitrofuroic acid with phosphorus oxychloride leads to the corresponding nitrile (2). This intermediate is then converted to the iminoether (3) with ethanolic hydrogen chloride. Condensation of anthranilic acid with the iminoether in the presence of sodium methoxide represents another method for preparing quinazolones. The reaction can be visualized as proceeding through the formation of the amidine from addition-elimination of anthranilic acid; cyclization then affords the observed product (4). The amide function is then converted to the iminochloride with phosphorus oxychloride. Displacement of the newly introduced halogen by means of diethanolamine affords nifurquinazol chlorine with diethanolamine leads to the formation of nifurquinazol (5), one of the antibacterial nitrofurans.

References

1. Dictionary of organic compounds. London: Chapman & Hall. 1996. ISBN 0-412-54090-8.
2. Sherman, W. R.; Von Esch, Anne (1965). "Syntheses with 5-Nitro-2-furonitrile". Journal of Medicinal Chemistry 8 (1): 25–28. doi:10.1021/jm00325a006. ISSN 0022-2623.
3. Burch, Homer A. (1966). "Nitrofuryl Heterocycles. IV1. 4-Amino-2-(5-nitro-2-furyl)quinazoline Derivatives". Journal of Medicinal Chemistry 9 (3): 408–410. doi:10.1021/jm00321a034. ISSN 0022-2623.