Chasing the Elusive Benzofuran Impurity of the THR Antagonist NH-3: Synthesis, Isotope Labeling, and Biological Activity

Latika Singh; Brandon Pressly; Brenda J. Mengeling; James C. Fettinger; John Furlow; Pamela J Lein; Heike Wulff; Vikrant Singh

doi:10.1021/acs.joc.5b02665

Chasing the Elusive Benzofuran Impurity of the THR Antagonist NH-3: Synthesis, Isotope Labeling, and Biological Activity

Latika Singh, Brandon Pressly, Brenda J. Mengeling, James C. Fettinger, John Furlow, Pamela J Lein, Heike Wulff, Vikrant Singh

Research output: Contribution to journal › Article

10 Scopus citations

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.

Original language	English (US)
Pages (from-to)	1870-1876
Number of pages	7
Journal	Journal of Organic Chemistry
Volume	81
Issue number	5
DOIs	https://doi.org/10.1021/acs.joc.5b02665
State	Published - Mar 4 2016

ASJC Scopus subject areas

Organic Chemistry

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Singh, L., Pressly, B., Mengeling, B. J., Fettinger, J. C., Furlow, J., Lein, P. J., Wulff, H., & Singh, V. (2016). Chasing the Elusive Benzofuran Impurity of the THR Antagonist NH-3: Synthesis, Isotope Labeling, and Biological Activity. Journal of Organic Chemistry, 81(5), 1870-1876. https://doi.org/10.1021/acs.joc.5b02665

Chasing the Elusive Benzofuran Impurity of the THR Antagonist NH-3 : Synthesis, Isotope Labeling, and Biological Activity. / Singh, Latika; Pressly, Brandon; Mengeling, Brenda J.; Fettinger, James C.; Furlow, John ; Lein, Pamela J ; Wulff, Heike; Singh, Vikrant.

In: Journal of Organic Chemistry, Vol. 81, No. 5, 04.03.2016, p. 1870-1876.

Research output: Contribution to journal › Article

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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.",

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