d-Glucose- and d-mannose-based antimetabolites. Part 2. Facile synthesis of 2-deoxy-2-halo-d-glucoses and -d-mannoses |
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Authors: | Izabela Fokt Slawomir Szymanski Stanislaw Skora Marcin Cybulski Timothy Madden Waldemar Priebe |
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Affiliation: | aDepartment of Experimental Therapeutics, The University of Texas M. D. Anderson Cancer Center, 1515 Holcombe Blvd., Houston, TX 77030, USA |
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Abstract: | Modified d-glucose and d-mannose analogs are potentially clinically useful metabolic inhibitors. Biological evaluation of 2-deoxy-2-halo analogs has been impaired by limited availability and lack of efficient methods for their preparation. We have developed practical synthetic approaches to 2-deoxy-2-fluoro-, 2-chloro-2-deoxy-, 2-bromo-2-deoxy-, and 2-deoxy-2-iodo derivatives of d-glucose and d-mannose that exploit electrophilic addition reactions to a commercially available 3,4,6-tri-O-acetyl-d-glucal. |
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Keywords: | 2-Deoxy-2-halo- smCaps" >d-glucose 2-Deoxy-2-halo- smCaps" >d-mannose Inhibitors of glycolysis Synthesis |
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