取代的7-甲基-2H,5H-吡喃并[4,3-b]吡喃-5-酮的高效合成及其体外抗增殖/细胞毒性活性评估。
Efficient synthesis of substituted 7-methyl-2H,5H-pyrano[4,3-b]pyran-5-ones and evaluation of their in vitro antiproliferative/cytotoxic activities.
作者信息
Leutbecher Heiko, Williams Lawrence A D, Rösner Harald, Beifuss Uwe
机构信息
Bioorganische Chemie, Institut für Chemie der Universität Hohenheim, Garbenstr. 30, 70599 Stuttgart, Germany.
出版信息
Bioorg Med Chem Lett. 2007 Feb 15;17(4):978-82. doi: 10.1016/j.bmcl.2006.11.045. Epub 2006 Nov 17.
Substituted 7-methyl-2H,5H-pyrano[4,3-b]pyran-5-ones and related heterocycles 3 were synthesized through an efficient domino Knoevenagel condensation/6pi-electron electrocyclization. In vitro antiproliferative/cytotoxic activity evaluation was performed with human SH-SY5Y neuroblastoma cells and revealed IC(50) values ranging from 6.7 to >200microM. The compound that was most cytotoxic to the neuroblastoma cells, that is, 2-isobutyl-3-isopropyl-7-methyl-2H,5H-pyrano[4,3-b]pyran-5-one (3a), also exhibited necrotic effects on the human IPC melanoma cells.
通过高效的多米诺Knoevenagel缩合/6π-电子电环化反应合成了取代的7-甲基-2H,5H-吡喃并[4,3-b]吡喃-5-酮及相关杂环化合物3。用人SH-SY5Y神经母细胞瘤细胞进行了体外抗增殖/细胞毒性活性评估，结果显示IC(50)值在6.7至>200μM之间。对神经母细胞瘤细胞毒性最大的化合物，即2-异丁基-3-异丙基-7-甲基-2H,5H-吡喃并[4,3-b]吡喃-5-酮(3a)，对人IPC黑色素瘤细胞也表现出坏死作用。
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