1-(1-indanyl)- and 1-(1-tetralyl)imidazole-5-carboxylate esters, a novel type of antifungal agents

E.F. Godefroi, J. Cutsem, van, C.A.M. Van der Eycken, P.A.J. Janssen

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Abstract

1-(1-Indanyl)imidazole-5-carboxylates (I) and 1-(1-tetralyl)imidazole-5-carboxylates (II) are synthesized and evaluated for antifungal activity. The N-(1-indanyl)- or N-(1-tetralyl)-N-formylglycine ester, OCHNRCH2CO2R1 (III, R = 1-indanyl, R1 = Me) (IV, R = 1-tetralyl, R1 = Et), undergoes Claisen formylation to the enolate, the enolate treated with HCl-HNCS, and the resulting N-(1-indanyl)- or N-(1-tetralyl)-2-mercaptoimidazole (V and VI, resp.) desulfurized and converted to the desired III via the acid and acid chloride. I and II exhibit excellent fungistatic activity against several organisms, including Microsporum canis, Trichophyton mentagrophytes, and T. rubrum. The optimum effect is achieved when R = Et or Pr, lengthening of the chain results in diminished activity, the introduction of bulky groups causes greatly diminished inhibition, and carboxylic acids are totally inactive.
Original languageEnglish
Pages (from-to)1160-1161
Number of pages2
JournalJournal of Medicinal Chemistry
Volume10
Issue number6
DOIs
Publication statusPublished - 1967

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