Allylamines, Morpholine Derivatives, Fluoropyrimidines, and Griseofulvin

Ishida, Kelly; Barroso, Vinícius de Morais

doi:10.1016/b978-0-12-809633-8.21025-x

Cited by 2 publications

(4 citation statements)

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“…Spiro[benzofuran-cyclohexane] skeletons are privileged structural motifs that construct the core of a broad range of naturally occurring compounds and pharmaceuticals (Figure ). For example, griseofuvin, initially isolated from Penicillium griseofulvum by Oxford and co-workers, is an FDA-approved fungistatic drug for the treatment of dermatophytosis caused by species of Microsporum and Trichophyton . Filifolinol is a naturally occurring scaffold that has been isolated in important quantities from Heliotropium filifolium Miers (Boraginaceae) and has been evidenced in antiviral activity .…”

Section: Introductionmentioning

confidence: 99%

Highly Regio- and Diastereoselective Phosphine-Catalyzed [2 + 4] Annulation of Benzofuran-Derived Azadienes with Allyl Carbonates: Access to Spiro[benzofuran-cyclohexanes]

Huang,

Tan,

Wang

et al. 2023

J. Org. Chem.

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A novel highly regio- and diastereoselective phosphine-catalyzed [2 + 4] annulation of benzofuran-derived azadienes (BDAs) with acidic hydrogen-tethered allyl carbonates has been developed ingeniously. A range of functionalized spiro[benzofuran-cyclohexane] derivatives with two consecutive stereocenters were smoothly obtained in moderate to excellent yields under mild reaction conditions from readily available materials. Moreover, this method is a practical and scalable strategy that creates the core structural motif of the fungistatic drug, griseofulvin.

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Section: Introductionmentioning

confidence: 99%

Highly Regio- and Diastereoselective Phosphine-Catalyzed [2 + 4] Annulation of Benzofuran-Derived Azadienes with Allyl Carbonates: Access to Spiro[benzofuran-cyclohexanes]

Huang,

Tan,

Wang

et al. 2023

J. Org. Chem.

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“…Furthermore, the concentration of luliconazole in the stratum corneum is estimated to be 130 μg/cm 2 at 24 h after the first topical application 15 . In turn, terbinafine is an allylamine drug whose activity results in intracellular accumulation of squalene, that is a metabolite that is toxic to fungal cells 16,17 . In consequence, terbinafine leads to rapid death of dermatophyte cells 16 .…”

Section: Introductionmentioning

confidence: 99%

“…15 In turn, terbinafine is an allylamine drug whose activity results in intracellular accumulation of squalene, that is a metabolite that is toxic to fungal cells. 16,17 In consequence, terbinafine leads to rapid death of dermatophyte cells. 16 Following topical administration to normal skin, cream-terbinafine formulations were found to attain concentrations ranging from 746 to 949 ng/cm 2 , as described elsewhere.…”

mentioning

confidence: 99%

“…16,17 In consequence, terbinafine leads to rapid death of dermatophyte cells. 16 Following topical administration to normal skin, cream-terbinafine formulations were found to attain concentrations ranging from 746 to 949 ng/cm 2 , as described elsewhere. [18][19][20] In 7-day application, high terbinafine concentration levels were found in stratum corneum (2-5 μg/cm 2 ), and a concentration of the drug higher than the minimal inhibitory concentration for most dermatophytes was still found 48 days after the last day of medication.…”

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confidence: 99%

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Therapeutic efficacy of topically used luliconazole vs. terbinafine 1% creams

Gnat

Dyląg

Łagowski

et al. 2021

Mycoses

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Dermatophytoses are the most common agents of superficial fungal infections in the world, affecting a substantial part of the human population. 1,2 The increased frequency of fungal infectious diseases recorded in the last several years can be attributed to environmental factors, lifestyle and adaptation of fungi to the environment. For example, improper hygiene, occlusive footwear, socioeconomic conditions, new types of professions, animal breeding in flats, frequent trips to warm climate regions, civilisation diseases such as diabetes mellitus, increasing resistance of pathogens to antifungal substances and even climate change have been attributed to this notable increase in the prevalence of fungal infections. [3][4][5][6][7][8] In recent years, the introduction of new antifungal agents has provided major advances in the therapy of dermatophytosis. 3,8,9 One of such drugs, luliconazole, was first approved for therapy in Japan in 2005.Later, it was approved in India and the United States in 2010 and 2013, respectively. 10,11 This drug has an imidazole moiety introduced into the ketene dithioacetate structure, which effectively interferes with ergosterol biosynthesis by inhibition of sterol 14 α-demethylase. 11,12

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Allylamines, Morpholine Derivatives, Fluoropyrimidines, and Griseofulvin

Cited by 2 publications

References 85 publications

Highly Regio- and Diastereoselective Phosphine-Catalyzed [2 + 4] Annulation of Benzofuran-Derived Azadienes with Allyl Carbonates: Access to Spiro[benzofuran-cyclohexanes]

Highly Regio- and Diastereoselective Phosphine-Catalyzed [2 + 4] Annulation of Benzofuran-Derived Azadienes with Allyl Carbonates: Access to Spiro[benzofuran-cyclohexanes]

Therapeutic efficacy of topically used luliconazole vs. terbinafine 1% creams

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