Nifurzide
Chemical compound
- A07AX04 (WHO)
- 5-Nitro-N′-[(1E,2E)-3-(5-nitro-2-furyl)-2-propen-1-ylidene]-2-thiophenecarbohydrazide
- 39978-42-2
Y
- 9571044
- 7845510
- Z35R6K4C26
- D07251
Y
![Edit this at Wikidata](http://upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png)
- Interactive image
- [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
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
- ^ 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.
- ^ US patent 3847911, Szarvasi E, Fontaine L, "Novel substituted(nitrofurylacrylidene)hydrazines with antibacterial properties", issued 1974-11-12
- ^ 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.
- ^ "Nifurzide". Pharmaceutical Substances. Thieme. Retrieved 2024-07-02.
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