68963-22-4Relevant academic research and scientific papers
Synthesis method of anthraquinone derivatives and tetracenedione derivatives through benzannulation reaction
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Paragraph 0049-0050; 0054, (2017/08/09)
The present invention relates to a method for synthesizing anthraquinone derivatives and tetracene dione derivatives through a benzannulation reaction, which presents a novel synthesis method, capable of processing synthesis easily, conveniently, and efficiently under mild conditions by an organic catalyst. The synthesis method uses an L-proline catalyst which is nontoxic, economical and easily available, compared to conventional production methods, thereby providing the anthraquinone derivatives and the tetracene dione derivatives through the one-pot benzannulation reaction of an α, β-unsaturated aldehyde compound, various 1,4-naphthoquinone compounds or 1,4-anthracenedione compounds. Various forms of anthraquinone derivatives or tetracene dione derivatives prepared by the synthesis method can be widely used for synthesis of natural products, dyes, and pharmaceutical products.COPYRIGHT KIPO 2017
Organocatalyzed benzannulation for the construction of diverse anthraquinones and tetracenediones
Somai Magar, Krishna Bahadur,Xia, Likai,Lee, Yong Rok
supporting information, p. 8592 - 8595 (2015/05/20)
An efficient one-pot synthesis of anthraquinones and tetracenediones was achieved vial-proline catalyzed [4+2] cycloaddition of in situ generated azadiene from α,β-unsaturated aldehydes and 1,4-naphthoquinones or 1,4-anthracenedione in good to excellent yield. This protocol constitutes an unprecedented tandem benzannulation that allows one-pot construction of diverse anthraquinones and tetracenediones in the presence of organocatalysts. This methodology was applied successfully to the synthesis of naturally occurring molecules and photochemically interesting phenanthrenequinone derivatives.
Design, synthesis, biochemical studies, cellular characterization, and structure-based computational studies of small molecules targeting the urokinase receptor
Wang, Fang,Eric Knabe,Li, Liwei,Jo, Inha,Mani, Timmy,Roehm, Hartmut,Oh, Kyungsoo,Li, Jing,Khanna, May,Meroueh, Samy O.
experimental part, p. 4760 - 4773 (2012/09/08)
The urokinase receptor (uPAR) serves as a docking site to the serine protease urokinase-type plasminogen activator (uPA) to promote extracellular matrix (ECM) degradation and tumor invasion and metastasis. Previously, we had reported a small molecule inhibitor of the uPAR·uPA interaction that emerged from structure-based virtual screening. Here, we measure the affinity of a large number of derivatives from commercial sources. Synthesis of additional compounds was carried out to probe the role of various groups on the parent compound. Extensive structure-based computational studies suggested a binding mode for these compounds that led to a structure-activity relationship study. Cellular studies in non-small cell lung cancer (NSCLC) cell lines that include A549, H460 and H1299 showed that compounds blocked invasion, migration and adhesion. The effects on invasion of active compounds were consistent with their inhibition of uPA and MMP proteolytic activity. These compounds showed weak cytotoxicity consistent with the confined role of uPAR to metastasis.
Regiocontrolled Diels-Alder Reactions of 9-Chloro-10-hydroxyanthracene-1,4-dione
Gupta, Ramesh C.,Jackson, David A.,Stoodley, Richard J.
, p. 929 - 930 (2007/10/02)
The title compound reacts with isoprene in the presence of aluminium chloride or boron trifluoride-ether to give the 2-methyl derivative of 6-chloro-11-hydroxy-1,4,4a,12a-tetrahydronaphthacene-5,12-dione; in the presence of boron triacetate, the 3-methyl isomer is the major product.
Regiochemical Control in the Diels-Alder Reaction of Substituted Naphthoquinones. The Directing Effects of C-6 Oxygen Substituents
Kelly, T. R.,Parekh, Nitin D.,Trachtenberg, Edward N.
, p. 5009 - 5013 (2007/10/02)
The Diels-Alder reactions of 6-hydroxy, 6-methoxy-, and 6-acetoxynaphthoquinone with trans-1-methoxy-3-methyl-1,3-butadiene have been studied, and the regiochemistry of the adducts has been determined.The results are consistent with the hypothesis that th
