Nifurzide

Nifurzide

Clinical data
AHFS/Drugs.com	International Drug Names
ATC code	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 InfoCard	100.049.735
Chemical and physical data
Formula	C12H8N4O6S
Molar mass	336.28 g·mol−1
3D 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

Esterification of 5-nitrothiophene-2-carboxylic acid (1) with ethanol gives the ester (2). Treatment with hydrazine forms its hydrazide (3). Nifurzide is the hydrazone formed between (3) and 5-nitrofuran-2-acrylaldehyde (4). ^{[2] [3] [4]}

References

1. 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.
2. USpatent 3847911,Szarvasi E, Fontaine L,"Novel substituted(nitrofurylacrylidene)hydrazines with antibacterial properties",issued 1974-11-12 
3. Szarvasi E, Fontaine L, Betbeder-Matibet A (March 1973). "Antimicrobials. New nitrofuran derivatives". Journal of Medicinal Chemistry. 16 (3): 281–287. doi:10.1021/jm00261a027. PMID   4200221.
4. "Nifurzide". Pharmaceutical Substances. Thieme. Retrieved 2024-07-02.