14353-86-7Relevant academic research and scientific papers
A concise and scalable strategy for the total synthesis of dictyodendrin B based on sequential C-H functionalization
Pitts, Andrew K.,O'Hara, Fionn,Snell, Robert H.,Gaunt, Matthew J.
supporting information, p. 5451 - 5455 (2015/04/27)
A sequential C-H functionalization strategy for the synthesis of the marine alkaloid dictyodendrin B is reported. Our synthesis begins from commercially available 4-bromoindole and involves six direct functionalizations around the heteroarene core as part of a gram-scale strategy towards the natural product.
Design, synthesis, and structure-activity relationship (SAR) of N-[7-(4-hydroxyphenoxy)-6-methylindan-4-yl]malonamic acids as thyroid hormone receptor β (TRβ) selective agonists
Shiohara, Hiroaki,Nakamura, Tetsuya,Kikuchi, Norihiko,Ozawa, Tomonaga,Matsuzawa, Akane,Nagano, Ryuichi,Ohnota, Hideki,Miyamoto, Takahide,Ichikawa, Kazuo,Hashizume, Kiyoshi
, p. 592 - 607 (2013/02/25)
Highly TRβ selective thyromimetics have several potential therapeutic applications. Based on the novel indane derivative KTA-439 with high receptor (TRβ) and organ (liver) selectivity, a series of thyroid hormone analogues were prepared, in which the isopropyl at the 3′-position was replaced with alkyl and aralkyl moieties of variable lengths and branches. Binding assays for these human TRs and reporter cell assays showed that 2-arylethyl derivatives had higher TRβ selectivity than KTA-439. KTA-574, a representative 2-arylethyl derivative, had TRβ specificity in a binding assay and exhibited full agonism in a reporter cell assay.
Discovery of novel indane derivatives as liver-selective thyroid hormone receptor β (TRβ) agonists for the treatment of dyslipidemia
Shiohara, Hiroaki,Nakamura, Tetsuya,Kikuchi, Norihiko,Ozawa, Tomonaga,Nagano, Ryuichi,Matsuzawa, Akane,Ohnota, Hideki,Miyamoto, Takahide,Ichikawa, Kazuo,Hashizume, Kiyoshi
experimental part, p. 3622 - 3634 (2012/07/27)
Thyromimetics that specifically target TRβ have been shown to reduce plasma cholesterol levels and avoid atherosclerosis through the promotion of reverse cholesterol transport in an animal model. We designed novel thyromimetics with high receptor (TRβ) and organ (liver) selectivity based on the structure of eprotirome (3) and molecular modeling. We found that indane derivatives are potent and dual-selective thyromimetics expected to avoid hypothyroidism in some tissues as well as heart toxicity. KTA-439 (29), a representative indane derivative, showed the same high human TRβ selectivity in a binding assay as 3 and higher liver selectivity than 3 in a cholesterol-fed rat model.
Cascade iodination-fluorination synthesis of 2-fluorothiophene and 5-fluoro-2-thienyliodonium salts
Onys'ko, Petro P.,Kim, Tetyana V.,Kiseleva, Olena I.,Rassukana, Yuliya V.,Gakh, Andrei A.
experimental part, p. 501 - 504 (2010/01/14)
The first synthesis of fluorine-containing 2-thienyliodonium salts was accomplished using cascade iodination-fluorination. According to this methodology, thiophene is first converted to bis(2-thienyl)iodonium hexafluorophosphate using an electrophilic iodination reaction. Upon heating with potassium fluoride, this salt undergoes regioselective fluorination producing 2-fluorothiophene. 2-Fluorothiophene is then iodinated again to yield fluorothienyliodonium salts.
Synthesis of Thyroid Hormone Analogues. Part 3. Iodonium Salt Approaches to SK&F L-94901
Hickey, Deirdre M. B.,Leeson, Paul D.,Novelli, Riccardo,Shah, Virendra P.,Burpitt, Brian E.,et al.
, p. 3103 - 3112 (2007/10/02)
The key step in the synthesis of L-3,5-dibromo-3'--thyronine, SK&F L-94901 (1), a novel, selective, and potent thyromimetic, is the formation of the hindered diaryl ether moiety.This paper describes an investigation into the formation of the required diaryl ether by copper-catalysed reaction both of symmetrical iodonium salts (2a) and (10) and mixed iodonium salts (2b-e) with protected dibromotyrosine (5).The importance of the counter-ion of the iodonium salt is discussed.This work is extended to a large-scale synthesis of SK&F L-94901 (1).
