Nafimidone

Nafimidone

Identifiers
CAS Number	64212-22-2
PubChem	CID 51200
ChemSpider	46394
UNII	HZU3IQ1EWW
Chemical data
Formula	C15H12N2O
Molar mass	236.27 g/mol
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

1. Tajana, A; Portioli, F; Subissi, A; Nardi, D (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, K. A.; Wallach, M. B.; Hirschfeld, D. R. (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.