163684-51-3Relevant articles and documents
Synthesis of 4-aryl-1,2,3-triazolyl appended natural coumarin-related compounds with antiproliferative and radical scavenging activities and intracellular ROS production modification
Bistrovi?,Stipani?ev,Opa?ak-Bernardi,Juki?,Martinez,Glava?-Obrovac, Lj,Rai?-Mali?
, p. 7531 - 7543 (2017)
Novel natural coumarin-based umbelliferone, herniarin and esculetin series linked to hydroxy- and methoxy-substituted and non-substituted phenyl rings through a 1,2,3-triazole spacer were provided by environmentally friendly click chemistry under microwave irradiation. The antioxidative activity of the compounds was evaluated by DPPH-scavenging activity and cyclic voltammetry assays. While adjacent 6- and 7-hydroxyl groups in coumarins made a major contribution to antioxidative power and a decrease of ROS production relative to esculetin, a p-methoxy-substituted phenyl moiety had an impact on pronounced and selective antiproliferative activity against chronic leukemia cells in blast crisis (K562) with no significant change in the ROS generation. 6,7-Dihydroxycoumarin can be considered as a promising scaffold with a major contribution to antioxidant potential and, thereby, further structural modification of 6,7-dihydroxycoumarin linked to aryl-1,2,3-triazole may provide a hybrid molecule that may be of interest for potential application to prevent diseases related to the oxidative-stress imbalance.
Synthesis of Coumarin-4-Ylmethyl Phosphonic Acids
Kondratyuk,Dluzhevskii,Bondarenko,Brovarets,Frasinyuk
, p. 632 - 637 (2019/08/02)
New coumarin-4-ylmethylphosphonates and coumarin-4-ylmethylphosphonic acids were synthesized and tested for antiviral activity.
Design and synthesis of tailored human caseinolytic protease P inhibitors
Gronauer, Thomas F.,Mandl, Melanie M.,Lakemeyer, Markus,Hackl, Mathias W.,Me?ner, Martina,Korotkov, Vadim S.,Pachmayr, Johanna,Sieber, Stephan A.
supporting information, p. 9833 - 9836 (2018/09/10)
Human caseinolytic protease P (hClpP) is important for degradation of misfolded proteins in the mitochondrial unfolded protein response. We here introduce tailored hClpP inhibitors that utilize a steric discrimination in their core naphthofuran scaffold to selectively address the human enzyme. This novel inhibitor generation exhibited superior activity compared to previously introduced beta-lactones, optimized for bacterial ClpP. Further insights into the bioactivity and binding to cellular targets were obtained via chemical proteomics as well as proliferation- and migration studies in cancer cells.
Preliminary structure-antiangiogenic activity relationships of 4-senecioyloxymethyl-6,7-dimethoxycoumarin.
Nam, Nguyen-Hai,Kim, Yong,You, Young-Jae,Hong, Dong-Ho,Kim, Hwan-Mook,Ahn, Byung-Zun
, p. 2345 - 2348 (2007/10/03)
Through a systematic modification of the novel angiogenesis inhibitor 4-senecioyloxymethyl-6,7-dimethoxycoumarin (1) we found that a 6,7-dimethoxy moiety is important for bioactivity of 1. Replacement of the lactone functionality in coumarin 1 by an amide decreased its activity. By substitution of the senecioyl chain with various cinnamoyl groups we discovered 6d, bearing a 4-methoxycinnamoyl instead of senecioyl side chain, with inhibitory activity in HUVEC tube formation assay enhanced by one order of magnitude compared to 1. We have also synthesized compound 12, an analogue of 6d, with equipotency and improved water solubility.
A CONVENIENT SYNTHESIS OF BENZOFURAN-3-ACETIC ACIDS
Fall, Yagamare,Santana, Lourdes,Teijeira, Marta,Uriarte, Eugenio
, p. 647 - 650 (2007/10/02)
We describe a two-step synthesis of benzofuran-3-acetic acids (1) from phenols (2) involving alkali-mediated rearrangement of 4-halomethylcoumarins (3) via α,β-unsaturated acids (4).Electron-donating substituents at the meta position of the phenol favour high yields of the coumarin, which in all cases rearranges to afford benzofuran-3-acetic acids in near quantitative yields.
