...
  • 主题
高级搜索  >
历史搜索 清空历史
首页> 外文期刊>New Journal of Chemistry >A combined experimental and theoretical rationalization of an unusual zinc(ii)-mediated conversion of 18-membered Schiff-base macrocycles to 18-membered imine-amine macrocycles with imidazolidine side rings: an investigation of their bio-relevant catalytic activities
【24h】

A combined experimental and theoretical rationalization of an unusual zinc(ii)-mediated conversion of 18-membered Schiff-base macrocycles to 18-membered imine-amine macrocycles with imidazolidine side rings: an investigation of their bio-relevant catalytic activities

机译：具有咪唑烷侧环的18元席克基碱宏杂环的异常锌（II）介导的转化率的综合实验性和理论合理化，咪唑烷侧环对18元酰胺 - 胺宏杂种：对其生物相关催化活性的研究

获取原文
获取原文并翻译 | 示例
           
页面导航
  • 摘要
  • 著录项
  • 相似文献
  • 相关主题

摘要

The 2 : 2 condensation reaction of 2,6-diformyl-4-isopropyl phenol and N '-(2-aminoethyl)ethane-1,2-diamine leads to a macrocycle Schiff base ligand (H2L) with the N6O2 chromophore, which in the presence of ZnX2 transforms into a new [2+2] 18 membered macrocyclic system (H2L1) with an N4O2 chromophore and two exo-cyclic imidazolidine rings. The transformation of H2L to H2L1 in the presence of ZnX2 is unique and was confirmed by single crystal X-ray diffraction. The structural analysis reveals that the transformation generates complexes with a dinuclear Zn(ii) core connected to a ZnX3 moiety, leading to trinuclear species with the composition [Zn-3(L-1)(X)(5)](CH3OH)(H2O). The complexes (X = Cl, 1 and X = Br, 2) are also isostructural, where the central and terminal Zn atoms have different coordination geometries (trigonal-bipyramidal and tetrahedral, respectively). A probable mechanistic pathway involved in the conversion of the 18-membered imine-imine macrocycles to 18-membered imine-amine macroycles with imidazolidine excyclic rings has been established by combined experimental and theoretical investigations. Both these complexes (1 and 2) were exploited to check their phosphatase-like activity using the disodium salt of 4-nitrophenylphosphate (4-NPP) as a model substrate in a 97.5% (v/v) DMF-H2O mixture. The turnover numbers (k(cat)) of complexes 1 and 2 were calculated to be 17.905 and 14.235 s(-1), respectively. The probable mechanistic pathway has been explored via trapping the intermediate species of the catalytic cycle by ESI-MS study. On considering the efficiency of the catalyst in phospho-ester bond hydrolysis, both complexes were tested for their anticancer activities on MDA-MB-231 (human breast cancer) and HeLa (cervical cancer) cell lines, as revealed by in vitro MTT assays. The better cell killing properties of complex 1 were further evidenced with the help of cell migration inhibition studies.
机译：2,6-二甲酰基-4-异丙基苯酚和N'-（2-氨基乙基）乙烷-1,2-二胺的2:2缩合反应生成一个大环席夫碱配体（H2L）和N6O2生色团，在ZnX2存在下，该配体转化为一个新的[2+2]18元大环系统（H2L1），带有一个N4O2生色团和两个外环咪唑啉环。在ZnX2存在下，H2L向H2L1的转化是独特的，并由单晶X射线衍射证实。结构分析表明，该转化生成了与ZnX3部分连接的双核Zn（ii）核的配合物，导致组成为[Zn-3（L-1）（X）（5）]（CH3OH）（H2O）的三核物种。配合物（X=Cl，1和X=Br，2）也是同构的，其中中心和末端的锌原子具有不同的配位几何形状（分别为三角双锥和四面体）。通过实验和理论研究相结合，建立了18元亚胺-亚胺大环转化为18元亚胺-胺大环和咪唑啉环的可能机制。在97.5%（v/v）的DMF-H2O混合物中，使用4-硝基苯磷酸二钠盐（4-NPP）作为模型底物，利用这两种复合物（1和2）来检查它们的磷酸酶样活性。计算出配合物1和配合物2的周转数（k（cat））分别为17.905和14.235s（-1）。ESI-MS研究通过捕获催化循环的中间物种探索了可能的机理途径。考虑到催化剂在磷酸酯键水解中的效率，体外MTT分析显示，这两种复合物在MDA-MB-231（人乳腺癌）和HeLa（宫颈癌）细胞系上的抗癌活性均得到了测试。在细胞迁移抑制研究的帮助下，复合物1具有更好的细胞杀伤性能。

著录项

  • 来源
    《New Journal of Chemistry》 |2021年第5期|共13页
  • 作者

    Chakraborty Tonmoy; Mukherjee Somali; Parveen Rumana; Chandra Arpita; Samanta Debabrata; Das Debasis;

  • 作者单位

    Univ Calcutta Dept Chem 92 APC Rd Kolkata 700009 India;

    Univ Calcutta Dept Chem 92 APC Rd Kolkata 700009 India;

    Univ Calcutta Dept Chem 92 APC Rd Kolkata 700009 India;

    Chittaranjan Natl Canc Inst In Vitro Carcinogenesis &

    Cellular Chemotherapy Kolkata 700026 India;

    Dukhulal Nibaran Chandra Coll Dept Chem Aurangabad 742201 W Bengal India;

    Univ Calcutta Dept Chem 92 APC Rd Kolkata 700009 India;

  • 收录信息
  • 原文格式 PDF
  • 正文语种 eng
  • 中图分类 化学;
  • 关键词

相似文献

  • 外文文献
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