194937-70-7Relevant academic research and scientific papers
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.
Approaches to the synthesis of arisugacin A
Jung, Michael E.,Min, Sun-Joon
, p. 3682 - 3701 (2007/10/03)
Approaches to the synthesis of the important acetylcholinesterase inhibitor, arisugacin A, are described. Two different routes to?the key AB ring system are described: the first utilizes an intramolecular Diels-Alder reaction on a furan substrate and the
Synthesis of the bis-potassium salts of 5-hydroxy-3-oxopent-4-enoic acids and their use for the efficient preparation of 4-hydroxy-2H-pyran-2-ones and other heterocycles
Schmidt, Dietmar,Conrad, Juergen,Klaiber, Iris,Beifuss, Uwe
, p. 4732 - 4734 (2007/10/03)
5-Hydroxy-3-oxopent-4-enoic acid esters can be efficiently transformed into the stable bis-potassium salts of the corresponding 5-hydroxy-3-oxopent-4-enoic acids, from which the sensitive acids are released in situ, the latter being converted into substit
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.
A One-Pot Condensation of Pyrones and Enals. Synthesis of 1H,7H-5a,6,8,9-Tetrahydro-1-oxopyrano[4,3-6][1]benzopyrans
Hua, Duy H.,Chen, Yi,Sin, Hong-Sig,Maroto, Maria J.,Robinson, Paul D.,Newell, Steven W.,Perchellet, Elisabeth M.,Ladesich, James B.,Freeman, Jonathan A.,Perchellet, Jean-Pierre,Chiang, Peter K.
, p. 6888 - 6896 (2007/10/03)
Condensation of various 6-substituted 4-hydroxypyrones 1 with 1-cyclohexenecarboxaldehydes in the presence of L-proline in ethyl acetate gave high yields of substituted 1H,7H-5a,6,8,9-tetrahydro-1-oxopyrano[4,3-6][1]benzopyrans. The reaction presumably oc
