Abstract
Retinoic acid analogues such as N-(4-hydroxyphenyl)retinamide (4-HPR) are effective chemopreventatives and chemotherapeutics for numerous types of cancer. The C-linked analogue of the O-glucuronide of 4-HPR (4-HPRCG) has been shown to be a more effective agent. The synthetic route to this molecule has been significantly improved by access to a key C-benzyl-glucuronide intermediate through employment of a Suzuki coupling reaction between an exoanomeric methylene sugar and an aryl bromide. Preliminary evidence shows 4-HPRCG has chemotherapeutic activity.
Publication types
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Research Support, U.S. Gov't, P.H.S.
MeSH terms
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Animals
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Antineoplastic Agents / chemical synthesis*
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Antineoplastic Agents / pharmacology
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Fenretinide / chemical synthesis*
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Fenretinide / pharmacology
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Glucuronides / chemical synthesis*
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Glucuronides / pharmacology
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Mammary Neoplasms, Experimental / drug therapy
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Mammary Neoplasms, Experimental / prevention & control
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Protein Binding
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Rats
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Receptors, Retinoic Acid / metabolism
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Retinoids / chemical synthesis
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Retinoids / pharmacology
Substances
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Antineoplastic Agents
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Glucuronides
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Receptors, Retinoic Acid
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Retinoids
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Fenretinide