Nafimidone

Nafimidone
Identifiers
CAS Number	64212-22-2 ;
PubChem CID	51200;
ChemSpider	46394 ;
UNII	HZU3IQ1EWW;
CompTox Dashboard (EPA)	DTXSID80214426 ;
Chemical and physical data
Formula	C15H12N2O
Molar mass	236.274 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C1=CC=C2C=C(C=CC2=C1)C(=O)CN3C=CN=C3;
	InChI InChI=1S/C15H12N2O/c18-15(10-17-8-7-16-11-17)14-6-5-12-3-1-2-4-13(12)9-14/h1-9,11H,10H2 ; Key:ITPVLJQRUQVNSD-UHFFFAOYSA-N ;
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Nafimidone is an anticonvulsant drug of the imidazole class. It contains a naphthyl group. It seems to have been discovered by accident during a search for antifungal agents.

Synthesis

Nafimidone synthesis:[1][2]

Its synthesis is straightforward displacement of imidazole of the activated chlorine atom of chloro-methyl-β-naphthylketone.

References

Tajana A, Portioli F, Subissi A, Nardi D (March 1981). "[N-Naphthacylimidazoles and N-((beta-naphthyl-beta-hydroxy)ethyl) imidazoles with anticonvulsant activity]". Bollettino Chimico Farmaceutico. 120 (3): 185–90. PMID 7272022.
Walker KA, Wallach MB, Hirschfeld DR (January 1981). "1-(Naphthylalkyl)-1H-imidazole derivatives, a new class of anticonvulsant agents". Journal of Medicinal Chemistry. 24 (1): 67–74. doi:10.1021/jm00133a015. PMID 7205879.

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[1] Tajana A, Portioli F, Subissi A, Nardi D (March 1981). "[N-Naphthacylimidazoles and N-((beta-naphthyl-beta-hydroxy)ethyl) imidazoles with anticonvulsant activity]". Bollettino Chimico Farmaceutico. 120 (3): 185–90. PMID 7272022.

[2] Walker KA, Wallach MB, Hirschfeld DR (January 1981). "1-(Naphthylalkyl)-1H-imidazole derivatives, a new class of anticonvulsant agents". Journal of Medicinal Chemistry. 24 (1): 67–74. doi:10.1021/jm00133a015. PMID 7205879.