棒曲霉素的非天然C-1同系物——合成及有前景的生物活性。
Unnatural C-1 homologues of pancratistatin - Synthesis and promising biological activities.
作者信息
Vshyvenko Sergey, Scattolon Jon, Hudlicky Tomas, Romero Anntherese E, Kornienko Alexander, Ma Dennis, Tuffley Ian, Pandey Siyaram
机构信息
Chemistry Department and Centre for Biotechnology, Brock University, 500 Glenridge Avenue, St. Catharines, ON L2S 3A1, Canada.
Chemistry Department, New Mexico Institute of Mining and Technology, 801 Leroy Place, Socorro, NM 87801, USA.
出版信息
Can J Chem. 2012;90(11):932-943. doi: 10.1139/v2012-073. Epub 2012 Sep 19.
Abstract
Several C-1 homologues of pancratistatin and 7-deoxypancratistatin were synthesized by a phenanthrene-phenathridone oxidative recyclization strategy. The key steps involved the enzymatic dihydroxylation of bromobenzene, addition of an aryl alane to an epoxyaziridine, an intramolecular aziridine opening on silica gel in solid phase, and the above-mentioned recylization strategy. Experimental and spectral data are reported for all new compounds. All synthesized C-1 homologues of pancratistatin and 7-deoxypancratistatin were evaluated for antiproliferative activity in a panel of human cancer cell lines. As expected, the 7-hydroxy compounds were found to be more potent and the activity of the C-1 benzoxymethyl analogue exceeded that of narciclasine, which was used as a positive control.
摘要
通过菲-菲啶酮氧化环化策略合成了几种泛克他汀和7-脱氧泛克他汀的C-1同系物。关键步骤包括溴苯的酶促二羟基化、芳基铝烷与环氧氮丙啶的加成、在硅胶上进行的分子内氮丙啶开环固相反应以及上述环化策略。报道了所有新化合物的实验和光谱数据。对所有合成的泛克他汀和7-脱氧泛克他汀的C-1同系物在一组人类癌细胞系中进行了抗增殖活性评估。正如预期的那样，发现7-羟基化合物活性更强，且C-1苯氧基甲基类似物的活性超过了用作阳性对照的水仙环素。
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