18692-95-0Relevant academic research and scientific papers
Total synthesis method of meroterpenoid natural product (+)-Arisugacins F/G
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Paragraph 0009; 0050; 0056; 0073-0075, (2020/03/12)
The invention discloses a total synthesis method of a meroterpenoid natural product (+)-Arisugacins F/G, and belongs to the field of organic synthesis. The method is as follows: using oleanolic acid as a chiral source starting raw material, and carrying out active group protection, free radical elimination, ring-opening reaction, cis-trans isomerization and oxidative hydrolysis to obtain a chiralintermediate aldehyde; then carrying out [3 + 3] cycloaddition reaction with pyrone, and carrying out hydrogenation reduction to generate (+)-Arisugacins F; and then carrying out an oxidation reactionto obtain (+)-Arisugacins G. According to the invention, the chiral source starting raw material oleanolic acid is commercially available, the reaction conditions of each unit in the reaction processare mild and controllable, the stereoselectivity of the key reaction is strong, and the method has potential application value in total synthesis of terpenoid natural products and drug discovery.
Total syntheses of (+)-arisugacins F, G
Chen, Ping,Li, Yu,Tang, Yu,Wu, Hao
supporting information, (2020/07/20)
(+)-Arisugacin F and G are synthesized from commercially available oleanolic acid in 9 and 10 steps, respectively. This strategy features a AgOTf/Pd(PPh3)4-mediated cis/trans olefin isomerization and a highly convergent formal oxa-[3 + 3] cycloaddition between key α, β-unsaturated aldehyde and pyrone, which lays the foundation for efficient and concise synthesis of other natural products with similar terpenoid scaffolds.
Antitumor agents 270. Novel substituted 6-phenyl-4H-furo[3,2-c]pyran-4-one derivatives as potent and highly selective anti-breast cancer agents
Dong, Yizhou,Shi, Qian,Nakagawa-Goto, Kyoko,Wu, Pei-Chi,Morris-Natschke, Susan L.,Brossi, Arnold,Bastow, Kenneth F.,Lang, Jing-Yu,Hung, Mien-Chie,Lee, Kuo-Hsiung
scheme or table, p. 803 - 808 (2010/04/26)
6-Phenyl-4H-furo[3,2-c]pyran-4-one derivatives based on neo-tashinlactone (1) were synthesized and evaluated as novel anti-breast cancer agents. Compounds 10-13, 23, 25, and 27 showed potent inhibition against the SK-BR-3 breast cancer cell line. Importantly, 25 and 27 showed the highest cancer cell line selectivity, being approximately 100-250-fold more potent against SK-BR-3 (ED50 0.28 and 0.44 μM, respectively) compared with other cancer cell lines tested. In addition, 25 displayed low cytotoxicity against normal breast cell lines 184A1 and MCF10A. Compounds 25 and 27 merit further investigation in our continuing program to generate and develop selective anti-breast cancer agents.
Synthesis and UV studies of a small library of 6-aryl-4-hydroxy-2- pyrones. A relevant structural feature for the inhibitory property of arisugacin against acetylcholinesterase
Douglas, Christopher J.,Sklenicka, Heather M.,Shen, Hong C.,Mathias, David S.,Degen, Shane J.,Golding, Geoffrey M.,Morgan, Christopher D.,Shih, Regina A.,Mueller, Kristen L.,Seurer, Lisa M.,Johnson, Erik W.,Hsung, Richard P.
, p. 13683 - 13696 (2007/10/03)
4-Hydroxypyrones belong to an important class of compounds not only because of their medicinal significance, but also because they represent a common structural feature among natural products that are biologically relevant. We describe here preparations of a small library of 6-aryl-4- hydroxy-pyrones which represent structural analogs of the DE-ring of arisugacin, a potent and selective inhibitor against acetylcholinesterase. Given the structural significance of the DE-ring in the inhibitory activity of arisugacin, chemical shifts of relevant protons on the pyrone ring are compared, and distinct features in UV absorptions of these 6-aryl-4-hydroxy- pyrones are described.
