Antifungal Agents, II: Synthesis and Antifungal Activities of Aryl‐1<i>H</i>‐pyrrol‐2‐yl‐1<i>H</i>‐imidazol‐1‐yl‐methane Derivatives with Unsaturated Chains

Massa, S.; Ragno, Rino; Porretta, Giulio Cesare; Mai, Antonello; Retico, A; Artico, Marco; Simonetti, N

doi:10.1002/ardp.19933260909

Cited by 8 publications

(4 citation statements)

References 9 publications

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“…The susceptibility of 40 clinical isolates of C. albicans to the new pyrroles at 256 pg/mL was determined and expressed as R% (percent of resistant strains). Among 44 derivatives tested at pH 7.2, only two (11 and 46) showed R = 100%, and for eight compounds (5,17,25,30,40,45, 47, and 48), more R were ranging from 2.7% to 50%. Like the controls (bifonazole, miconazole, and ketoconazole), the remaining derivatives at 256 pg/mL inhibited all of the clinical isolates employed in the experiments.…”

Section: Discussionmentioning

confidence: 97%

Antifungal Agents. 9. 3-Aryl-4-[.alpha.-(1H-imidazol-1-yl)arylmethyl]pyrroles: A New Class of Potent Anti-Candida Agents

Artico

Santo²,

Costi³

et al. 1995

J. Med. Chem.

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A new class of potent antifungal agents, namely, 3-aryl-4-[alpha-(1H-imidazol-1-yl)arylmethyl]-pyrroles, is described. These compounds are related to bifonazole and pyrrolnitrin, two compounds belonging to the class of antimycotic drugs. The synthesis of the title pyrroles has been performed starting from 1,3-diaryl-2-propen-1-ones, which were reacted with tosylmethyl isocyanide to give 3-aroyl-4-arylpyrroles. Reduction of the resulting compounds by lithium aluminum hydride furnished the related alcohols, which were treated with 1,1'-carbonyldimidazole to afford the required imidazole derivatives. Forty-four new pyrroles which incorporate an (arylmethyl)imidazole moiety in the 3-arylpyrrole structure were prepared by the above procedure and tested in vitro against Candida albicans and Candida spp. Among test compounds, 10 were found to be highly active against C. albicans. The most active derivative (27) was twice as potent (MIC90) as bifonazole, and its activity was 4 times greater than those of miconazole and ketoconazole. The other nine compounds showed antifungal activity of the same order of that of bifonazole and were ca. 2 times as active as miconazole and ketoconazole. Derivatives 21 and 27 tested in vivo against C. albicans A170 were shown to be highly effective in rabbit skin candidosis. Pharmacological studies on compounds 27 and other related pyrroles (19, 35, 36, 38, 39, and 49) are in progress to select one of them as a potential candidate for clinical experiments.

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Section: Discussionmentioning

confidence: 97%

Antifungal Agents. 9. 3-Aryl-4-[.alpha.-(1H-imidazol-1-yl)arylmethyl]pyrroles: A New Class of Potent Anti-Candida Agents

Artico

Santo²,

Costi³

et al. 1995

J. Med. Chem.

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“…[13] Method A, colorless oil, yield (GC): 6%. [14] Method B, pale yellow oil, yield (GC): 94%. [15] Method A (140°C, toluene, aldehyde/amine ϭ 2:1), pale yellow solid, m.p.…”

Section: Catalytic Reaction With Oxidant (Methods B)mentioning

confidence: 99%

“…66°C (EtOH), yield (GC): 30%. N-(4-Methoxybenzyl)morpholine: [16] [17] N-(Cyclohexylcarbonyl)morpholine: [18] [16] (14). [19] N-Octanoylmorpholine: [20]…”

Section: Catalytic Reaction With Oxidant (Methods B)mentioning

confidence: 99%

Catalytic Amination of Aldehydes to Amides

2001

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Aldehydes react in a disproportionation reaction in the presence of rhodium catalysts to yield amines and amides. By adding N-methylmorpholine N-oxide as an oxidant in the presence of catalytic amounts of rhodium, the oxidative am- [a] 523 ination of aldehydes proceeds selectively to give the corresponding amide. Both aliphatic and aromatic aldehydes react with secondary amines to yield carboxylic acid amides in good to excellent yields.

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“…N ‐(4‐Fluorobenzoyl)morpholine: 14 Method B, pale yellow oil, yield (GC): 94%. − 1 H NMR (400 MHz, CDCl 3 ): δ = 2.95 (m, br, 8 H, 4 CH 2 ), 7.0, 7.5 (4 H, Ph).…”

Section: Methodsmentioning

confidence: 99%

Catalytic Amination of Aldehydes to Amides

2001

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Aldehydes react in a disproportionation reaction in the presence of rhodium catalysts to yield amines and amides. By adding N‐methylmorpholine N‐oxide as an oxidant in the presence of catalytic amounts of rhodium, the oxidative amination of aldehydes proceeds selectively to give the corresponding amide. Both aliphatic and aromatic aldehydes react with secondary amines to yield carboxylic acid amides in good to excellent yields.

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Antifungal Agents, II: Synthesis and Antifungal Activities of Aryl‐1H‐pyrrol‐2‐yl‐1H‐imidazol‐1‐yl‐methane Derivatives with Unsaturated Chains

Cited by 8 publications

References 9 publications

Antifungal Agents. 9. 3-Aryl-4-[.alpha.-(1H-imidazol-1-yl)arylmethyl]pyrroles: A New Class of Potent Anti-Candida Agents

Antifungal Agents. 9. 3-Aryl-4-[.alpha.-(1H-imidazol-1-yl)arylmethyl]pyrroles: A New Class of Potent Anti-Candida Agents

Catalytic Amination of Aldehydes to Amides

Catalytic Amination of Aldehydes to Amides

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