Nifurzide

Chemical compound

A07AX04 (WHO)

Identifiers

IUPAC name

5-Nitro-N′-[(1E,2E)-3-(5-nitro-2-furyl)-2-propen-1-ylidene]-2-thiophenecarbohydrazide

CAS Number

39978-42-2^Y

PubChem CID

9571044

ChemSpider

7845510

UNII

Z35R6K4C26

KEGG

D07251^Y

ECHA InfoCard100.049.735

Chemical and physical dataFormulaC₁₂H₈N₄O₆SMolar mass336.28 g·mol⁻¹3D model (JSmol)

Interactive image

SMILES

[O-][N+](=O)c1ccc(o1)/C=C/C=N/NC(=O)c2ccc(s2)[N+](=O)[O-]

InChI

InChI=1S/C12H8N4O6S/c17-12(9-4-6-11(23-9)16(20)21)14-13-7-1-2-8-3-5-10(22-8)15(18)19/h1-7H,(H,14,17)/b2-1+,13-7+
Key:IDUMOVRJNBNOTR-BIZLIJPVSA-N

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Nifurzide is a nitrofuran derivative and intestinal anti-infectious agent active against Escherichia coli.^[1]

Synthesis

The esterification of 5-Nitrothiophene-2-carboxylic acid [6317-37-9] (1) with ethanol gives Ethyl 5-nitrothiophene-2-carboxylate [5751-84-8] (2). Treatment with hydrazine leads to 5-Nitro-2-thenoylhydrazide [39978-44-4] (3). Hydrazone formation with 5-Nitrofuran-2-acrylaldehyde [52661-56-0] [1874-22-2] (4) completes the synthesis of Nifurzide (5).

References

^ Delsarte A, Faway M, Frère JM, Coyette J, Calberg-Bacq CM, Heinen E (March 1981). "Nifurzide, a nitrofuran antiinfectious agent: interaction with Escherichia coli cells". Antimicrobial Agents and Chemotherapy. 19 (3): 477–86. doi:10.1128/aac.19.3.477. PMC 181457. PMID 7018391.
^ Castaer, J.; Serradell, MN; Blancafort, P.; Neuman, M.; Nifurzide. Drugs Fut 1981, 6, 6, 358.
^ Szarvasi, Etienne; Fontaine, Louis; Betbeder-Matibet, Annie (1973). "Antimicrobials. New nitrofuran derivatives". Journal of Medicinal Chemistry. 16 (3): 281–287. doi:10.1021/jm00261a027.
^ L Fontaine, E Szarvasi, U.S. patent 3,847,911 (1974 to Lipha, Lyonnaise Industrielle Pharmaceutique).
^ Etienne Szarvasi, Louis Fontaine, U.S. patent 3,914,379 (1975 to Lipha).