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4,5-Diazafluorene N-glycopyranosyl hydrazones as scaffolds for potential bioactive metallo-organic compounds: Synthesis, structural study and cytotoxic activity
Bioorganic Chemistry ( IF 5.1 ) Pub Date : 2018-09-01 , DOI: 10.1016/j.bioorg.2018.08.019
Sebastian Jäger , Lourdes Gude , María-Selma Arias-Pérez

A series of novel N1-(4,5-diazafluoren-9-yliden)-N2-glycopyranosyl hydrazines was prepared in synthetically useful yields by treatment of 9H-4,5-diazafluoren-9-hydrazone with different unprotected monosaccharides. The reactions with the monosaccharides tested afforded stereoselectively, and exclusively, cyclic derivatives, whose structures correspond to N-β-glycopyranosyl hydrazones except for the d-arabinose derivative that agrees with the α-anomer. Several copper(II) complexes having a 2:1 ligand to metal mole ratio were also prepared. The metal complexes can bind DNA sequences and preferentially stabilize G-quadruplex DNA structures over dsDNA. The fucose, rhamnose and deoxyglucose copper(II) complexes exhibited a cytotoxic activity against cultured HeLa and PC3 tumor cells comparable to other metal complexes normally used for chemotherapeutic purposes, such as cisplatin.



中文翻译:

4,5-二氮杂芴N -glycopyranosyl azo用作潜在的生物活性金属有机化合物的支架:合成,结构研究和细胞毒活性

通过用不同的未保护的单糖处理9 H -4,5-二氮杂芴基-9- in,以合成有用的产率制备了一系列新颖的N 1-(4,5-二氮杂芴-9-li基)-N 2-甘氨酰呋喃糖基肼。与测试的单糖的反应可立体选择性地提供环状衍生物,其结构对应于N -β-甘露糖基,除了d-与α-端基异构体一致的阿拉伯糖衍生物。还制备了几种配体与金属的摩尔比为2:1的铜(II)配合物。金属配合物可以结合DNA序列,并且比dsDNA优先稳定G-四链体DNA结构。岩藻糖,鼠李糖和脱氧葡萄糖铜(II)配合物对培养的HeLa和PC3肿瘤细胞显示出与通常用于化学治疗目的的其他金属配合物(如顺铂)相当的细胞毒活性。

更新日期:2018-09-01
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