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Analogues of bifonazole bearing two imidazole rings and other related azoles have been synthesized and tested as antifungal agents against Candida albicans and Candida spp.. Only a slight part of the antifungal power of the parent drug is retained by some derivatives as evinced by the comparison of new compounds with bifonazole, miconazole, and ketoconazole.

The synthesis and antifungal activities against Candida albicans and Candida spp. of some pyrrole analogues of bifonazole are reported. 1-{p-Methyl-α-[4-(1H-pyrrol-1-yl)phenyl]benzyl}imidazole was found to be equipotent or sometimes superior to bifonazole and ketoconazole, and lightly inferior to miconazole. Substitution of the imidazole moiety with other azoles retained some activities. No activity was shown when the azole aromatic rings were replaced by the heteroalicyclic ones. Uber antibakterielle und antimykotische Wirkstoffe, 10. Mitt.: Synthese und antimykotische Eigenschaften von 1-{p-Methyl-α-[4-(1H-pyrrol-1-yl)phenyl]benzyl}azole und einiger verwandter Verbindungen Synthese und antimykotische Eigenschaften einiger Pyrrol-Analoge des Bifonazols gegen Candida albicans und Candida spp. werden beschrieben. 1-{p-Methyl-α-[4-(1H-pyrrol-1-yl)phenyl]benzyl)imidazol ist gleichermasen oder starker wirksam als Bifonazol oder Ketoconazol und etwas schwacher wirksam als Miconazol. Bei Substitution des Imidazol-Systems durch andere Azole blieb die Aktivitat teilweise erhalten. Wurde dagegen der aromatische Azolring durch heteroalicyclische Gruppen ersetzt, so war keine Aktivitat mehr nachzuweisen.

The synthesis and antimicrobial activities of derivatives of 1-anilinopyrrole and 1-pyrrylbenzimidazole are described. The compounds here reported can be related to chlormidazole and other antifungal imidazole agents. The antifungal activity of the new derivatives tested proved lower than that of ketoconazole; some compounds were practically inactive.

A new analog of nalidixic acid, 1-ethyl-1,4-dihydro-4-oxo--7-(1-pyrryl)quinoline-3-carboxylic acid, is described. When tested against gram-positive and gram-negative bacteria this compound showed many significant activities and was more active than nalidixic, piromidic and pipemidic acids. On the contrary its 6-chloro- and 6-methylderivatives lack antimicrobial activities. All new compounds here described were synthesized by standard procedures via Gould-Jacobs reaction.

The synthesis of 1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1H-pyrrol-1-yl)quinoline-3-carboxy lic acid, a new fluorinated high broad-spectrum antibacterial agent related to nalidixic acid is described. The title compound has been prepared by the reaction of 4-fluoro-3-(1H-pyrrol-1-yl)aniline with diethyl ethoxymethylenemalonate, cyclization of the malonate obtained to the quinolinecarboxylate ester, ethylation of the ester, followed by hydrolysis with aqueous sodium hydroxide. The new derivative proved very active against both gram-positive and gram-negative bacteria. Its activities in comparison with those of nalidixic acid, pipemidic acid, piromidic acid and enoxacin were found to be greatly superior with regard to the unfluorinated compounds and somewhat superior also to enoxacin. The known 1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(pyrrolidin-1-yl)quinoline-3- carboxylic acid, here prepared by catalytic hydrogenation of the pyrrole moiety of the title compound, has been found to be less active as an antibacterial agent.

The synthesis and antifungal activities of 1-aryl-4-p-nitrophenylimidazoles and their 2-mercaptoderivatives is reported. Antimicrobial data in comparison with antifungal antibiotic pyrrolnitrin attributed the best activity to 1-p-methoxyphenyl-4-p-nitrophenylimidazole. The tested compounds were prepared by reacting p-nitrophenacylanilines with potassium thiocyanate in acidic medium to afford 1-aryl-2-mercapto-4-p-nitrophenylimidazoles, which were then transformed into the title compound by treatment with nitric acid.

The synthesis and antibacterial activities of 4-hydroxyquinoline-3-carboxylic acid and 1,4-dihydro-1-ethyl-4-oxoquinoline-3-carboxylic acid containing a pyrrole or 2,5-dimethylpyrrole group at 6 position are reported. Reaction of 1-(4-aminophenyl)pyrrole or 2,5-dimethyl-1-(4-aminophenyl)-pyrrole with ethoxymethylenemalonate diethyl ester (EMME) afforded the related pyrroleanilinomethylenemalonates, which were subjected to thermal cyclization to give the required quinoline derivatives. These compounds on ethylation furnished at last the quinolonecarboxylic analogs of nalidixic acid.

Les composes etudies sont des acides methyl-2 nitro-4' phenyl-5 pyrrolecarboxyliques-3 substitues en 1 par un groupe phenyl porteur d'halogenes et/ou d'un groupe trifluoromethyl, leurs alkylamides, leurs methyl-4' piperazides et les derives chloro-4 correspondants

The synthesis and antibacterial activities of 1-ethyl-1,4-dihydro-4-oxo-7-(1-pyrrolidinyl)quinoline-3-carboxylic acid are reported. The new analog of nalidixic acid has been prepared by standard procedure starting from 1-(3-aminophenyl)pyrrole; it showed a broad spectrum of antibacterial activity and exhibited much higher activity than nalidixic, pipemidic and piromidic acids. The synthesis of 1-ethyl-1,4-dihydro-4-oxo-8-(1-pyrrolyl)quinoline-3-carboxylic acid is also described; this acid was inactive when tested as antibacterial agent.