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Kabachnik-fields phosphorylation of tetaraene macrolide antibiotic pimaricin

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Abstract

Polyene macrolide antibiotic pimaricin reacts with dialkyl(diaryl) phosphites and 4-bromobenzaldehyde to form 3′-N-α-[dialkoxy(diphenoxy)phosphinoyl]benzyl derivatives. Physicochemical and biological properties of the synthesized derivatives have been studied. According to the biological assay, the 3′-N-α-[dialkoxy(diphenoxy)phosphinoyl]benzyl derivatives are less toxic than the parent antibiotic and exhibit strong antifungal activity towards a wide range of Candida yeast-like fungi.

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  1. Faculty of Chemistry, Technion-Israel Institute of Technology, Haifa, Israel

    V. V. Belakhov

  2. St. Petersburg State Institute of Technology (Technical University), St. Petersburg, Russia

    A. V. Garabadzhiu

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  1. V. V. Belakhov
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Original Russian Text © V.V. Belakhov, A.V. Garabadzhiu, 2015, published in Zhurnal Obshchei Khimii, 2015, Vol. 85, No. 2, pp. 236–244.

To the 80th Anniversary of B.I. Ionin

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Belakhov, V.V., Garabadzhiu, A.V. Kabachnik-fields phosphorylation of tetaraene macrolide antibiotic pimaricin. Russ J Gen Chem 85, 409–417 (2015). https://doi.org/10.1134/S1070363215020103

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