191668-25-4Relevant articles and documents
N-(1-naphthylmethyl)-N-(1-alkyl-4-aryl-1H-pyrrol-3-yl methyl)methylamines related to naftifine. Synthesis and antifungal activity
Di Santo, Roberto,Costi, Roberta,Artico, Marino,Massa, Silvio,Musiu, Chiara,Milia, Carlo,Putzolu, Monica,La Colla, Paolo
, p. 98 - 108 (2007/10/03)
Various pyrrole analogues of the antifungal drug naftifine were prepared starting from cinnamates via the tosylmethylisocyanide (TosMIC) reaction. After alkylation and hydrolysis, the intermediate arylpyrrole esters afforded 1-alkyl-4-aryl-1H-pyrrole-3-carboxylic acids, which were condensed with N-(1-naphthylmethyl)methylamine in the presence of EDCI and triethylamine. The related amides were then reduced with lithium aluminum hydride to the required N-(1-naphthylmethyl)-N-(1-alkyl-4-aryl-1H-pyrrol-3-ylmethyl)methylamines. The new compounds were evaluated for antifungal activity in comparison with naftifine and other imidazole drugs used in the clinic. Derivative 7c was active against Candida parapsilosis and compound 51 against Candida albicans. Weak activity against dermatophytes was shown by a number of derivatives. Moreover, compounds 4g, 4j, 4k and 4p were found active against Staphylococcus aureus with potencies comparable to that of streptomycin.
