1333375-01-1Relevant academic research and scientific papers
Novel Carbazole-Based N-Heterocyclic Carbene Ligands to Access Synthetically Relevant Stilbenes in Pd-Catalyzed Coupling Processes
Girase, Tejpalsingh Ramsingh,Kapdi, Anant R.
supporting information, p. 2611 - 2619 (2019/07/05)
A series of new carbazole-based N-heterocyclic carbene (NHC) ligands have been synthesized in a simple and facile synthetic route and subsequently used in a Pd/carbazole-based NHC catalytic system, which was found to be effective in catalyzing Heck reactions to provide substituted stilbene derivatives in good yields. Several bioactive stilbenes, including pterostilbene, pinosylvin, trimethoxy resveratrol, and resveratrol, were synthesized in good yields, and a 10 mmol scale-up was also performed for trimethoxy resveratrol. The synthetic application was also extended by performing a double-tandem chemoselective Heck reaction followed by Miyaura borylation in a one-pot procedure to give single-step access to synthetically useful stilbenyl boronate esters. Similarly, a unique triple-tandem protocol of a chemoselective Heck reaction/Miyaura borylation/Suzuki–Miyaura coupling reaction sequence was performed for the one-pot modification of biologically relevant molecules.
Synthesis of Pinacolylboronate-Substituted Stilbenes and their application to the synthesis of boron capped polyenes
Das, Bhaskar C.,Mahalingam, Sakkarapalayam M.,Das, Sasmita,Hosmane, Narayan S.,Evans, Todd
, p. 51 - 59 (2015/12/18)
A series of novel 4,4,5,5-tetramethyl-2-(4-substitutedstyrylphenyl)-1,3,2 dioxaborolane derivatives has been synthesized. 4-(4,4,5,5-tetramethyl-1,3,2-dioxaboratophenyl)-methyl triphenylphosphonium bromide (4) was treated with 3 equiv of tBuONa, various a
NOVEL LIPOGENIC INHIBITORS AND USES THEREOF
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Page/Page column 33-34, (2012/09/10)
The present invention provides resveratrol-based boron-containing analog! methods of use thereof in treatment of dyslipidemias and cancer.
Design, synthesis and biological study of pinacolyl boronate-substituted stilbenes as novel lipogenic inhibitors
Das, Bhaskar C.,Zhao, Xiaoping,Tang, Xiang-Ying,Yang, Fajun
, p. 5638 - 5641 (2011/10/12)
A pilot library of novel 4,4,5,5-tetramethyl-2-(4-substitutedstyrylphenyl)- 1,3,2 dioxaborolane derivatives has been synthesized. 4-(4,4,5,5-Tetramethyl-1, 3,2-dioxaboratophenyl)-methyl triphenylphosphonium bromide 3 was treated with various aldehydes in the presence of 3 equiv of tBuONa in DMF, and stirred at room temperature for 4-6 h to yield the corresponding boron-containing stilbene derivatives in 71-94% yields. Several of them, including BF102 and BF175, have the lipogenesis inhibitory effect by suppressing lipogenic gene expression in mammalian hepatocytes. Further, BF102 also inhibits cholesterol biosynthesis by suppressing HMG-CoA reductase gene expression in hepatocytes. Interestingly, our preliminary in vivo data suggests that BF102 has no significant toxicity in mice at the highest possible dose we can administered. Thus, BF102 is a potential lead for the next generation of lipid-lowering drugs.
