- Synthesis, functionalization and biological activity of arylated derivatives of (+)-estrone
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Various novel arylated estrone derivatives, such as 2-aryl-, 4-aryl- and 2,4-diaryl-estrones, by Suzuki-Miyaura reactions. While the synthesis of 4-arylestrones could be carried out under standard conditions, the synthesis of 2-arylestrones and 2,4-diarylestrones required a thorough optimization of the conditions and it proved to be important to use sterically encumbered biaryl ligands. The best results were obtained by the use of RuPhos. Combination of developed Suzuki coupling reactions with subsequent cyclization reactions afforded more complex hybrid structures, containing dibenzofuran, benzocoumarin and steroid moieties. These derivatives were tested as pancreatic lipase inhibitors and it was found that most of the compounds exhibited inhibition of pancreatic lipase but the maximum inhibitory potential was shown by 4-arylestrones. All of the synthesized derivatives showed inhibitory values in the range of 0.82 ± 0.01–59.7 ± 3.12 μM. The biological activity was also rationalized on the bases of docking studies.
- Ivanov, Anton,Ejaz, Syeda Abida,Shah, Syed Jawad Ali,Ehlers, Peter,Villinger, Alexander,Frank, Eva,Schneider, Gyula,W?lfling, János,Rahman, Qamar,Iqbal, Jamshed,Langer, Peter
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p. 949 - 962
(2017/02/05)
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- Pentavalent Organobismuth Reagents. Part 2. The Phenylation of Phenols.
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The phenylation of a variety of phenols by pentavalent bismuth reagents under neutral, acid and basic conditions has been investigated.Under basic conditions well defined pentavalent intermediates have been isolated and fully characterised.Their decomposition gives only ortho-C-phenylation (except in the case of a p-nitrophenol derivative).O-Phenylation is seen under neutral or acidic conditions.Another mechanism is proposed to explain this reaction with no pentavalent bismuth intermediate.
- Barton, Derek H. R.,Bhatnagar, Neerja Yadav,Blazejewski, Jean-Claude,Charpiot, Brigitte,Finet, Jean-Pierre,et al.
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p. 2657 - 2666
(2007/10/02)
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- Comparative arylation reactions with pentaphenylbismuth and with triphenylbismuth carbonate
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Pentaphenylbismuth is a useful reagent for the specific ortho-phenylation of phenols under very mild conditions, a comparison of this reagent with triphenylbismuth carbonate being drawn; arylation reactions of the carbonate have been extended to include nitrocompounds and amides.
- Barton, Derek H. R.,Blazejewski, Jean-Claude,Charpiot, Brigitte,Lester, David J.,Motherwell, William B.,Barros Papoula, M. Teresa
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p. 827 - 829
(2007/10/02)
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