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 | |
| State | Published - Mar 4 2016 |
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ASJC Scopus subject areas
- Organic Chemistry
Cite this
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
}
TY - JOUR
T1 - Chasing the Elusive Benzofuran Impurity of the THR Antagonist NH-3
T2 - Synthesis, Isotope Labeling, and Biological Activity
AU - Singh, Latika
AU - Pressly, Brandon
AU - Mengeling, Brenda J.
AU - Fettinger, James C.
AU - Furlow, John
AU - Lein, Pamela J
AU - Wulff, Heike
AU - Singh, Vikrant
PY - 2016/3/4
Y1 - 2016/3/4
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=84960153149&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84960153149&partnerID=8YFLogxK
U2 - 10.1021/acs.joc.5b02665
DO - 10.1021/acs.joc.5b02665
M3 - Article
C2 - 26849160
AN - SCOPUS:84960153149
VL - 81
SP - 1870
EP - 1876
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 5
ER -