E. F. Godefroi, J. V. van Cutsem, C. A. Van Der Eycken
Nov 1, 1967
Citations
0
Influential Citations
8
Citations
Quality indicators
Journal
Journal of medicinal chemistry
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.