引用本文:
林丽, 徐庆, 唐燕辉, 陈国荣. 6-O-苯甲酰基苯醌碳糖苷的合成及抗肿瘤活性[J]. 应用化学,
2007, 24(10): 1109-1114.
Citation: LIN Li, XU Qing, TANG Yan-Hui, CHEN Guo-Rong. Synthesis and Anti-tumor Activity of 6-O-Benzoyl C-Glycosyl Benzoquinone[J]. Chinese Journal of Applied Chemistry, 2007, 24(10): 1109-1114.
Citation: LIN Li, XU Qing, TANG Yan-Hui, CHEN Guo-Rong. Synthesis and Anti-tumor Activity of 6-O-Benzoyl C-Glycosyl Benzoquinone[J]. Chinese Journal of Applied Chemistry, 2007, 24(10): 1109-1114.
6-O-苯甲酰基苯醌碳糖苷的合成及抗肿瘤活性
摘要:
通过异亚丙基和苄基的选择性保护和脱保护法,分别方便地合成了6位带有自由羟基的半乳糖和葡萄糖,并进一步选择性地对其进行6位苯甲酰基化修饰从而获得相应糖给体。从6位苯甲酰基化半乳糖和葡萄糖糖给体出发,立体专一性地合成了β-构型的芳香碳糖苷中间体,再经硝酸铈铵(CAN)温和氧化烷氧基苯获得6-O-苯甲酰基苯醌碳糖苷目标化合物,其中4个结构未见文献报道。经1H NMR、13C NMR谱及高分辨质谱测试技术分析确证了目标化合物结构。采用MTT法考察了目标化合物对黑色素肿瘤细胞株A375的体外抑制活性。结果表明,2-(2,3,4-三-O-乙酰基-6-O-苯甲酰基-β-D-吡喃半乳糖)-1,4-苯醌(6)和2-(2,3,4-三-β)-乙酰基-6-O-苯甲酰基-β-D-吡喃葡萄糖)-1,4-苯醌(15)显示体外抗肿瘤活性。对此类化合物进一步的结构优化,开发高选择性、高活性的抗肿瘤先导化合物提供了信息。
English
Synthesis and Anti-tumor Activity of 6-O-Benzoyl C-Glycosyl Benzoquinone
Abstract:
Galactopyranose and glucopyranose with 6-position hydroxyl were conveniently synthesized by selective protection and deprotection of isopropylidene group and benzyl group respectively. Selective benzoylation on 6-position of galactose and glucose could be achieved from the 6-position hydroxyl compounds and then β-aryl C-glycoside intermediates were obtained with high stereoselectivity by means of introducing the glycosyl donors onto 1,4-dimethoxyl benzene. Under moderate oxidation with CAN(ceric ammonium nitrate), 6-O-benzoyl C-glycosyl benzoquinones were prepared and for of them have not been reported. The structures of target compounds were confirmed by 1H NMR, 13C NMR and HRMS spectroscopy. Anti-tumor activity tests including IC50 by MTT tetrazolium dye assay against human melanoma A375 cell line were carried out. The results show that 6-O-benzoyl C-glycosyl benzoquinones possess moderate anti-tumor activity. This character will make them useful in the structure modification and discovery of some potential antitumor with high selectivity and high activity.
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Key words:
- selective O-modification
- / C-glycosyl benzoquinones
- / synthesis
- / anti-tumor activity
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