Novel antifungals based on 4-substituted imidazole: A combinatorial chemistry approach to lead discovery and optimization

Liu, Li; Simoneaux, Richard; Kukla, Michael J.; Marichal, Patrick; Odds, Frank C.

doi:10.1016/s0960-894x(00)00445-5

Cited by 35 publications

(14 citation statements)

References 11 publications

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“…13) [28]. The type (28) compounds had good antifungal properties against the Candida strains when these were tested with minimum inhibitory concentration (MIC) values similar to those of the reference drug (30). Interestingly these types of azoles were found to have a cidal character against Candida albicans while the reference drug oxiconazole was only fungistatic in the same tests.…”

Section: Imidazole Containing Antifungal Agentsmentioning

confidence: 99%

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Author Index to Volume 12

2006

curr med chem

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Imidazoles are an important class of heterocycles and include many substances of both biological and chemical interest. They are part of a large number of highly significant biomolecules such as the essential amino acid histidine and related compounds, biotin, and the imidazole alkaloids. Insertion of the imidazole nucleus is an important synthetic strategy in drug discovery. Imidazole drugs have broad applications in many areas of clinical medicine. The imidazoles are a class of antifungal azole derivatives and have a broad spectrum of activities both in vitro and in vivo. The imidazole moiety is also contained in many histaminergic ligands for histamine H1, H2, and H3 receptors. These are currently used as tools in pharmacological studies. The important therapeutic properties of imidazole related drugs have encouraged the medicinal chemists to synthesize and test a large number of novel molecules. Some of these have chemotherapeutic properties, such as for example several FTase inhibitors with an imidazole moiety. Imidazole derivatives have also been shown to have antibacterial activity and recently several P38 MAP Kinase inhibitors and 5-Lipoxygenase inhibitors containing the imidazole moiety have been synthesized. This review reports current progress in the area of new biologically active imidazoles and recently discovered naturally occurring imidazole.

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Section: Imidazole Containing Antifungal Agentsmentioning

confidence: 99%

“…A series of 4-substituted imidazole sulfonamides were prepared by solid-phase chemistry [30]. These compounds were found to have good in vitro antifungal activity and are the first examples of C-linked azoles with such activity.…”

Section: Imidazole Containing Antifungal Agentsmentioning

confidence: 99%

Author Index to Volume 12

2006

curr med chem

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“…These compounds were found to have good in vitro anti-fungal activity and constitute the first example of C-linked azoles with such activity. The most potent inhibitor 4-butoxy-N-(1-cyclohexyl-propyl)-N-(3H-imidazol-4-ylmethyl)-benzenesulfonamide 49 demonstrated inhibition of key Candida strains at an in vitro concentration of less than 100 nM (Saha et al, 2000b).…”

Section: Imidazoles As Anti-bacterial Agentsmentioning

confidence: 99%

Biological importance of imidazole nucleus in the new millennium

2010

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Imidazole nucleus is a constituent of many bioactive heterocyclic compounds that are of wide interest because of their diverse biological and clinical applications. This created interest in researchers to synthesize variety of imidazole derivatives and to screen them for their various biological activities viz. anti-cancer, antiviral, antiHIV, anti-protozoal, anti-mycobacterial, antiinflammatory, analgesic, anxiolytic, as well anti-diabetic activities.

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“…Aiming the discovery of new antifungal agents, Saha and co-workers 202 described a combinatorial chemistry approach to 4-substituted imidazole sulfonamides using 4-formyl-imidazole (193) as the starting material. The imidazole N-1 atom was first attached to support prior to synthesis and cleaved after synthesis, thus allowing for traceless synthesis of target compounds.…”

Section: Alkaloidsmentioning

confidence: 99%

“…5,2003 substituent (201). Cascade radical annulation with an isonitrile (202) bearing the A-ring substituent then produces the mappicine analogues. The above route was conducted in four separate parallel synthesis experiments in a 4 x 4 x 1 manner by using 4 different isonitriles, 4 different propargyl bromides, and one iodopyridone.…”

Section: Alkaloidsmentioning

confidence: 99%

Natural Product‐Like Combinatorial Libraries

Abreu

Branco

2004

ChemInform

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A química combinatorial emergiu ao longo dos últimos anos como uma importante ferramenta na pesquisa de moléculas pioneiras para a modelagem de novos fármacos. Nesta perspectiva, a diversidade estrutural e a vasta gama de propriedades biológicas exibidas pelos metabolitos secundários, constituem um desafio à implementação de estratégias combinatórias na síntese e derivatização de produtos naturais. Este artigo ilustra a aplicação das técnicas combinatórias no desenho e formação de bibliotecas baseadas em produtos naturais de diversa origem biossintética, e seus análogos estruturais.Combinatorial chemistry has emerged over the last few years as an important tool for drug discovery and lead optimisation. In this approach, the molecular diversity and range of biological properties displayed by secondary metabolites constitutes a challenge to combinatorial strategies for natural products synthesis and derivatization. This article surveys the application of combinatorial techniques to the design of "natural product-looking" libraries covering a wide range of structural diversities.

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Novel antifungals based on 4-substituted imidazole: A combinatorial chemistry approach to lead discovery and optimization

Cited by 35 publications

References 11 publications

Author Index to Volume 12

Author Index to Volume 12

Biological importance of imidazole nucleus in the new millennium

Natural Product‐Like Combinatorial Libraries

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