cis-dichloro(1,4,8,11-tetraazabicyclo[6.6.2]hexadecane)cobalt(III) chloride | 1443429-89-7

• 英文名称: cis-dichloro(1,4,8,11-tetraazabicyclo[6.6.2]hexadecane)cobalt(III) chloride
• CAS: 1443429-89-7
• 化学式: C₁₂H₂₆Cl₂CoN₄*Cl
• 分子量: 391.717
• InChiKey: SECRQOSJUGZAAX-UHFFFAOYSA-K

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
  None
• 可旋转键数：
  None
• 环数：
  None
• sp3杂化的碳原子比例：
  None
• 拓扑面积：
  None
• 氢给体数：
  None
• 氢受体数：
  None

反应信息

• 作为反应物：
  描述：

  cis-dichloro(1,4,8,11-tetraazabicyclo[6.6.2]hexadecane)cobalt(III) chloride 以 甲醇 为溶剂， 反应 5.5h， 生成 8-quinolinolato(1,4,8,11-tetraazabicyclo[6.6.2]hexadecane)cobalt(III) perchlorate
  参考文献：
  名称：

  Cross-Bridged Cyclen or Cyclam Co(III) Complexes Containing Cytotoxic Ligands as Hypoxia-Activated Prodrugs

  摘要：

  A series of cobalt(III) complexes of the potent DNA minor groove alkylator (1-(chlorornethyl)-5-hydroxy-1H-pyrrolo [3,2-f]quinolin-3 (2H) -yl) (5,6,7- trim ethoxy-1H-indol-2-yl)methancine (3; seco-CPyI-TMI), with cyclam or cyclen auxiliary ligands (L3 and L5) containing a cross-bridging ethylene (CH2CH2) group or the N,N'-dimethyl derivatives of these (L4 and L6), was prepared. Two 8-quinolinato (2) model complexes of these, [Co(L3)(2)](ClO4)(2) and [Co(L6)(2)](ClO4)(2), and the aquated derivative [Co(L6)(H2O)(2)](OTf)(3) were characterized by X-ray Crystallography. Electrochemistry of the 8-quinolinato model complexes showed that the Co(III)/(II) reduction potential Was lowered relative to the unsubstituted cyclen ligand. Evaluation of the cytotoxicity of the racemic seco-CPyI cobalt complexes in vitro showed considerable attenuation of their cytotoxicity relative to the free alkylator and marked hypoxic selectivity, especially [Co(L3)(3)](2+) (9), which was 81-212-fold more potent under hypoxia than 20% oxygen in a panel of 10 human tumor cell lines. However, 9 did not elicit significant killing of hypoxic cells in HT29 tumor xenografts suggesting possible pharmacological limitations in vivo.

  DOI：

  10.1021/ic4006967
• 作为产物：
  描述：

  trans-dichlorotetra(pyridine)cobalt(III) chloride hexahydrate 、 1,4,8,11-四氮杂双环[6.6.2]十六烷 以 甲醇 为溶剂， 反应 1.0h， 以71%的产率得到cis-dichloro(1,4,8,11-tetraazabicyclo[6.6.2]hexadecane)cobalt(III) chloride
  参考文献：
  名称：

  Cross-Bridged Cyclen or Cyclam Co(III) Complexes Containing Cytotoxic Ligands as Hypoxia-Activated Prodrugs

  摘要：

  A series of cobalt(III) complexes of the potent DNA minor groove alkylator (1-(chlorornethyl)-5-hydroxy-1H-pyrrolo [3,2-f]quinolin-3 (2H) -yl) (5,6,7- trim ethoxy-1H-indol-2-yl)methancine (3; seco-CPyI-TMI), with cyclam or cyclen auxiliary ligands (L3 and L5) containing a cross-bridging ethylene (CH2CH2) group or the N,N'-dimethyl derivatives of these (L4 and L6), was prepared. Two 8-quinolinato (2) model complexes of these, [Co(L3)(2)](ClO4)(2) and [Co(L6)(2)](ClO4)(2), and the aquated derivative [Co(L6)(H2O)(2)](OTf)(3) were characterized by X-ray Crystallography. Electrochemistry of the 8-quinolinato model complexes showed that the Co(III)/(II) reduction potential Was lowered relative to the unsubstituted cyclen ligand. Evaluation of the cytotoxicity of the racemic seco-CPyI cobalt complexes in vitro showed considerable attenuation of their cytotoxicity relative to the free alkylator and marked hypoxic selectivity, especially [Co(L3)(3)](2+) (9), which was 81-212-fold more potent under hypoxia than 20% oxygen in a panel of 10 human tumor cell lines. However, 9 did not elicit significant killing of hypoxic cells in HT29 tumor xenografts suggesting possible pharmacological limitations in vivo.

  DOI：

  10.1021/ic4006967