134022-84-7Relevant academic research and scientific papers
A Formal [3 + 2] Alkene Addition to Benzhydrol Cations. A Practical and Mild Methodology for the Synthesis of Substituted 1-Arylindanes and Related Compounds
Lantano, Beatriz,Aguirre, Jose M.,Finkieisztein, Liliana,Aiesso, Elba N.,Brunet, Ernesto,Moltrasio, Graciela Y.
, p. 625 - 641 (2004)
We report the single step synthesis of several 1-arylindanes in good yield via a formal [3 + 2] atom cycloaddition. The success of this formal cycloaddition relies on the Lewis acid activation of a bibenzylic alcohol in the presence of an alkene. The cati
Natural-Product-Inspired Compounds as Countermeasures against the Liver Carcinogen Aflatoxin B1
Carter, Adam C.,King, Jarrod B.,Mattes, Allison O.,Cai, Shengxin,Singh, Narender,Cichewicz, Robert H.
, p. 1694 - 1703 (2019/06/08)
Aflatoxin B1 (AfB1) ranks among the most potent liver carcinogens known, and the accidental or intentional exposure of humans and livestock to this toxin remains a serious global threat. One protective measure that had been proposed is employing small-molecule therapeutics capable of mitigating the toxicity of AfB1; however, to date, these efforts have had little clinical success. To identify molecular scaffolds that reduce the toxicity of AfB1, we developed a cell-based high-throughput high-content imaging assay that enabled our team to test natural products (pure compounds, fractions, and extracts) for protection of monolayers and spheroids composed of HepG2 liver cells against AfB1. The spheroid assay showed notable potential for further development, as it afforded greater sensitivity of HepG2 cells to AfB1, which is believed to better mimic the in vivo response of hepatocytes to the toxin. One of the most bioactive compounds to arise from this investigation was alternariol-9-methyl ether (1, purified from an Alternaria sp. isolate), which inspired the synthesis and testing of several structurally related molecules. Based on these findings, it is proposed that several types of natural and synthetic polyarene molecules that have undergone oxidative functionalization (e.g., compounds containing 3-methoxyphenol moieties) are promising starting points for the development of new agents that protect against AfB1 toxicity.
Traceless azido linker for the solid-phase synthesis of N H-1,2,3-triazoles via Cu-catalyzed azide - Alkyne cycloaddition reactions
Cohrt, A. Emil,Jensen, Jakob F.,Nielsen, Thomas E.
supporting information; experimental part, p. 5414 - 5417 (2011/03/19)
A broadly useful acid-labile traceless azido linker for the solid-phase synthesis of NH-1,2,3-triazoles is presented. A variety of alkynes were efficiently immobilized on a range of polymeric supports by Cu(I)-mediated azide - alkyne cycloadditions. Suppo
Chemistry of photogenerated α-phenyl-substituted o-, m-, and p-quinone methides from phenol derivatives in aqueous solution
Diao, Li,Wan, Peter
, p. 105 - 118 (2008/09/18)
The enhanced photochemical reactivity of o-substituted phenols in its propensity to give o-quinone methide (o-QM) intermediates via excited state intramolecular proton transfer (ESIPT) was uncovered by Keith Yates as part of his now classic studies of photohydration of aromatic alkenes, alkynes, and related compounds. Photogeneration of QMs and the study of their chemistry along with potential biological applications are the focus of many groups. In this work, photochemical precursors to o-, m-, and p-QMs based on substituted phenols (hydroxybenzyl alcohols) and related compounds have been studied in aqueous solution as a function of pH and water content. The focus will be on QMs that are stabilized by an a-phenyl substituent, which enhances quantum yields for their formation, with the resulting QMs having longer lifetimes and easier to detect. Noteworthy is that all QM isomers can. be photogenerated with the o and m isomers being the most efficient, consistent with the Zimmerman "ortho-meta" effect. m-QMs have formal non-Kekule structures, and although they can be routinely photogenerated, are found to be most reactive. One m-QM was found, to undergo a photocondensation reaction at high pH giving rise to m-substituted oligomers. The mechanism, of QM formation in aqueous solution is believed to involve singlet excited phenols that undergo adiabatic deprotonation to give the corresponding photoexcited phenolate ion, which subsequently expels the hydroxide ion (photodehydroxylation). A pathway involving direct loss of water for the o-isomers is also possible in organic solvents.
