• 主题
高级搜索  >
历史搜索 清空历史
首页> 外文期刊>RSC Advances >Synthesis, structural studies and biological properties of some phosphono-perfluorophenylalanine derivatives formed by SNAr reactions
【24h】

Synthesis, structural studies and biological properties of some phosphono-perfluorophenylalanine derivatives formed by SNAr reactions

机译：SNAr反应形成的某些膦酰基全氟苯丙氨酸衍生物的合成，结构研究和生物学性质

获取原文
           
页面导航
  • 摘要
  • 著录项
  • 相似文献
  • 相关主题

摘要

Several novel phosphono-perfluorophenylalanine derivatives, as mimetics of phenylalanine, were synthesized by subjecting diethyl (2-(perfluorophenyl)-1-(phenylamino)ethyl)-phosphonate to S _(N) Ar reactions with different types of nucleophiles such as thiols, amines and phenols. The structure of the products was confirmed using spectroscopic and spectrometric techniques. For two compounds X-ray single crystal diffraction analysis and DFT investigations were performed providing information in regard to the preferable conformation, hydrogen bonds and other interactions. The antiproliferative potency of some of the new phosphono-perfluorophenylalanine derivatives obtained as well as representatives of previously synthesized perfluorophenyl phosphonate analogues of phenylalanine was studied on selected glioma cell lines. Preliminary evaluation of the compounds drug likeness was examined with respect to Lipinski's and Veber's rules, and showed that they meet the criteria perfectly. MTT (3-(4,5-dimethyl-2-thiazolyl)-2,5-diphenyl-2 H -tetrazolium bromide) assay results demonstrated that the compounds exhibit moderate activity against the glioblastoma multiforme cell lines (T98G and U-118 MG). Moreover most of the studied S _(N) Ar reaction products displayed significantly higher inhibitory activity against both cancer cell lines than the parent diethyl (2-(perfluorophenyl)-1-(phenylamino)ethyl)phosphonate.
机译：通过使（2-（全氟苯基）-1-（苯基氨基）乙基）-膦酸二乙酯与S_（N）Ar反应与不同类型的亲核试剂（例如硫醇）进行合成，合成了几种新颖的膦酰基全氟苯基丙氨酸衍生物，作为苯丙氨酸的模拟物胺和酚。使用光谱学和光谱学技术确认了产物的结构。对两种化合物进行了X射线单晶衍射分析和DFT研究，提供了有关优选构象，氢键和其他相互作用的信息。在选定的神经胶质瘤细胞系上研究了一些新的膦酰基全氟苯基丙氨酸衍生物的抗增殖能力以及以前合成的苯丙氨酸全氟苯基膦酸酯类似物的代表。根据Lipinski's和Veber's规则对化合物的相似性进行了初步评估，结果表明它们完全符合标准。 MTT（3-（4,5-二甲基-2-噻唑基）-2,5-二苯基-2 H-四唑溴化物）分析结果表明，该化合物对多形性胶质母细胞瘤细胞系（T98G和U-118 MG）具有中等活性）。而且，大多数研究的S_（N）Ar反应产物显示出对两种癌细胞系的抑制活性明显高于母体（2-（全氟苯基）-1-（苯基氨基）乙基）膦酸酯。

著录项

相似文献

  • 外文文献
  • 中文文献
  • 专利
获取原文

客服邮箱：kefu@zhangqiaokeyan.com

京公网安备：11010802029741号 ICP备案号：京ICP备15016152号-6 六维联合信息科技 (北京) 有限公司©版权所有

  • 客服微信

  • 服务号