mer-[RuCl(DMSO)3(3-(1H-benzimidazol-2-yl)-5-bromo-1H-pyrazolo[3,4-b]pyridine(-1H))]*H2O | 1351282-04-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: mer-[RuCl(DMSO)3(3-(1H-benzimidazol-2-yl)-5-bromo-1H-pyrazolo[3,4-b]pyridine(-1H))]*H2O
• 英文别名: 3-(1H-benzimidazol-2-yl)-5-bromopyrazolo[3,4-b]pyridin-1-ide;methylsulfinylmethane;ruthenium(2+);chloride;hydrate
• CAS: 1351282-04-6
• 化学式: C₁₉H₂₅BrClN₅O₃RuS₃*H₂O
• 分子量: 702.079
• InChiKey: GYUBYMFAIMCZCB-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -0.95
• 重原子数：
  34
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  165
• 氢给体数：
  2
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  [RuCl(4-formylphenoxyacetyl-η6-benzylamide)(3-(1H-benzimidazol-2-yl)-5-bromo-1H-pyrazolo[3,4-b]pyridine(-1H))]*H2O 以 二甲基亚砜 为溶剂， 生成 mer-[RuCl(DMSO)3(3-(1H-benzimidazol-2-yl)-5-bromo-1H-pyrazolo[3,4-b]pyridine(-1H))]*H2O
  参考文献：
  名称：

  Conjugation of Organoruthenium(II) 3-(1H-Benzimidazol-2-yl)pyrazolo[3,4-b]pyridines and Indolo[3,2-d]benzazepines to Recombinant Human Serum Albumin: a Strategy To Enhance Cytotoxicity in Cancer Cells

  摘要：

  Following our strategy of coupling cyclin-dependent kinase (Cdk) inhibitors with organometallic moieties to improve their physicochemical properties and bioavailability, five organoruthenium complexes (1c-5c) of the general formula [RuCl(eta(6)-arene)(L)]Cl have been synthesized in which the arene is 4-formylphenoxyacetyl-eta(6)-benzylamide and L is a Cdk inhibitor [3-(1H-benzimidazol-2-yl)-1H-pyrazolo[3,4-b]pyridines (L1-L3) and indolo[3,2-d]benzazepines (L4 and L5)]. All of the compounds were characterized by spectroscopic and analytical methods. Upon prolonged standing (2-3 months) at room temperature, the dimethyl sulfoxide (DMSO) solutions of 1c and 2c-(HCl) afforded residues, which after recrystallization from EtOH and EtOH/H2O, respectively, were shown by X-ray diffraction to be cis,cis-[(RuCl2)-Cl-II(DMSO)(2)(L1)]center dot H2O and mer-[(RuCl)-Cl-II(DMSO)(3)(L2-H)]center dot H2O. Compound 5c, with a coordinated amidine unit, undergoes E/Z isomerization in solution. The antiproliferative activities and effects on the cell cycle of the new compounds were evaluated. Complexes 1c-5c are moderately cytotoxic to cancer cells (CH1, SW480, A549, A2780, and A2780cisR cell lines). Therefore, in order to improve their antiproliferative effects, as well as their drug targeting and delivery to cancer cells, 1c-5c were conjugated to recombinant human serum albumin, potentially exploiting the so-called "enhanced permeability and retention" effect that results in the accumulation of macromolecules in tumors. Notably, a marked increase in cytotoxicity of the albumin conjugates was observed in all cases.

  DOI：

  10.1021/ic201801e