Abstract
We have synthesized and established the structure of a long-suspected, but hitherto unknown, benzofuran side product (EBI) formed during the synthesis of NH-3. Understanding the mechanism of its formation has enabled isotope (D) labeling. We further developed a highly efficient method for separating EBI from NH-3. Interestingly, EBI was found to be a very potent thyroid hormone receptor (THR) agonist, while NH-3 is an antagonist. In this process, we have also achieved a significantly improved synthesis of NH-3.
Publication types
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Research Support, U.S. Gov't, Non-P.H.S.
MeSH terms
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Benzofurans / chemical synthesis*
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Benzofurans / chemistry
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Benzofurans / pharmacology
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Benzyl Compounds / chemical synthesis*
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Benzyl Compounds / chemistry
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Benzyl Compounds / pharmacology
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Biological Phenomena
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Cyclization
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Isotope Labeling
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Nitro Compounds / chemical synthesis*
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Nitro Compounds / chemistry
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Nitro Compounds / pharmacology
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Nitroso Compounds / chemical synthesis*
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Nitroso Compounds / chemistry
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Nitroso Compounds / pharmacology
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Receptors, Thyroid Hormone / agonists*
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Receptors, Thyroid Hormone / chemistry*
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Receptors, Thyroid Hormone / metabolism
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Structure-Activity Relationship
Substances
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2-(4-((7-Isopropyl-2-(4-nitrophenyl)benzofuran-5-yl)methyl)-3,5-dimethylphenoxy)acetic acid
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2-(4-(4-hydroxy-3-isopropyl-5-((4-nitrophenyl)ethynyl)benzyl)-3,5-dimethylphenoxy)acetic acid
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Benzofurans
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Benzyl Compounds
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Nitro Compounds
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Nitroso Compounds
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Receptors, Thyroid Hormone