Applying of 1,1,1‐Trichloro‐2,2‐bis(4‐methoxyphenyl)ethane for the Synthesis of Diphenols

Lesiak, T.; Nowakowski, J.

doi:10.1002/prac.19813230423

Cited by 5 publications

(3 citation statements)

References 15 publications

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“…The vascular endothelium is the major barrier for a cardiovascular system fighting against oxidative stress injury and inflammation [ 1 ]. In recent years, various novel skeleton halophenols derived from natural marine algaes and their derivatives obtained by structural optimization have been discovered showing the excellent vascular endothelial protective properties [ 2 , 3 , 4 , 5 , 6 , 7 , 8 , 9 , 10 , 11 , 12 ]. In support of these growing interests, we expanded upon the continuing structural optimization and mechanistic investigation on halophenols for finding a candidate compound.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Novel Nitrogen-Containing Heterocycle Bromophenols and Their Interaction with Keap1 Protein by Molecular Docking

et al. 2017

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We previously reported 5,2’-dibromo-2,4’,5’-trihydroxydiphenylmethanoe (LM49), a bromophenol analogue that shows strong protection from oxidative stress injury owing to its superior anti-inflammatory, antioxidant, and anti-apoptotic properties. A series of novel nitrogen-containing heterocycle bromophenols were herein synthesized by introducing substituted piperidine, piperazine, and imidazole to modify 2-position of the lead compound LM49. By further evaluating their cytoprotective activity against H2O2 induced injury in EA.hy926 cells, 14 target bromophenols showed moderate-to-potent activity with EC50 values in the range of 0.9–6.3 μM, which were stronger than that of quercetin (EC50: 18.0 μM), a positive reference compound. Of these, the most potent compound 22b is a piperazine bromophenol with an EC50 value of 0.9 μM equivalent to the LM49. Molecular docking studies were subsequently performed to deduce the affinity and binding mode of derived halophenols toward the Keap1 Kelch domain, the docking results exhibited that the small molecule 22b is well accommodated by the bound region of Keap1-Kelch and Nrf2 through stable hydrogen bonds and hydrophobic interaction, which contributed to the enhancement of affinity and stability between the ligand and receptor. The above facts suggest that 22b is a promising pharmacological candidate for further cardiovascular drug development. Moreover, the targeting Keap1-Nrf2 protein-protein interaction may be an emerging strategy for halophenols to selectively and effectively activate Nrf2 triggering downstream protective genes defending against injury.

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Section: Introductionmentioning

confidence: 99%

Synthesis of Novel Nitrogen-Containing Heterocycle Bromophenols and Their Interaction with Keap1 Protein by Molecular Docking

et al. 2017

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“…Subsequent demethylation of 3 , 4 and 5 to compounds 6 , 7 and 8 , respectively, was performed using Py·HCl …”

Section: Resultsmentioning

confidence: 99%

“…Subsequent demethylation of 3, 4 and 5 to compounds 6, 7 and 8, respectively, was performed using Py‚HCl. 26 Thus, the dimethoxy-substituted compounds 3-5 were treated with Py‚HCl at 230 °C, affording the desired o-, m-, and p-tetraaryl BPA isomers in excellent yields. Spectroscopic data were in agreement with the structure of compounds 6, 7, and 8.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of High Aspect Ratio Bisphenols and Polycarbonates Incorporating Bisaryl Units

et al. 2005

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Theoretical arguments linking monomer geometries to polymer fracture strengths and melt flow properties provide the rationale for design of a series of isomeric, high-aspect ratio bisphenols and new polycarbonates. An efficient synthesis of these monomers in addition to an optimal triphosgenation-based method for the synthesis of high molecular weight polycarbonates is presented. Preparation and polymerization of o-, meta-, and p-tetraaryl bisphenol A are reported, in addition to glass transition temperatures of the new polycarbonates. In accordance with expectations, the p- and m- isomers form ductile, amorphous high-heat films, while the o-isomer produces a relatively low-T g brittle glass.

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ChemInform Abstract: APPLYING OF 1,1,1‐TRICHLORO‐2,2‐BIS(4‐METHOXYPHENYL)ETHANE FOR THE SYNTHESIS OF DIPHENOLS

Lesiak¹,

Nowakowski²

1981

Chemischer Informationsdienst

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Applying of 1,1,1‐Trichloro‐2,2‐bis(4‐methoxyphenyl)ethane for the Synthesis of Diphenols

Cited by 5 publications

References 15 publications

Synthesis of Novel Nitrogen-Containing Heterocycle Bromophenols and Their Interaction with Keap1 Protein by Molecular Docking

Synthesis of Novel Nitrogen-Containing Heterocycle Bromophenols and Their Interaction with Keap1 Protein by Molecular Docking

Synthesis of High Aspect Ratio Bisphenols and Polycarbonates Incorporating Bisaryl Units

ChemInform Abstract: APPLYING OF 1,1,1‐TRICHLORO‐2,2‐BIS(4‐METHOXYPHENYL)ETHANE FOR THE SYNTHESIS OF DIPHENOLS

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