cis-bis(triflato)(4,10-dimethyl-1,4,7,10-tetraaza-bicyclo-[5.5.2]tetradecane)cobalt(III) triflate | 1443429-83-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: cis-bis(triflato)(4,10-dimethyl-1,4,7,10-tetraaza-bicyclo-[5.5.2]tetradecane)cobalt(III) triflate
• CAS: 1443429-83-1
• 化学式: CF₃O₃S*C₁₄H₂₆CoF₆N₄O₆S₂
• 分子量: 732.57
• InChiKey: QDWORDCUGPMYGD-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-bis(triflato)(4,10-dimethyl-1,4,7,10-tetraaza-bicyclo-[5.5.2]tetradecane)cobalt(III) triflate 、 1-(chloromethyl)-5-hydroxy-3-[(5,6,7-trimethoxyindol-2-yl)carbonyl]-2,3-dihydro-1H-pyrrolo[3,2-f]quinoline 在 吡啶 作用下， 以 甲醇 为溶剂， 反应 216.0h， 以84%的产率得到1-(chloromethyl)-3-(5,6,7-trimethoxyindol-2-ylcarbonyl)-2,3-dihydro-1H-pyrrolo[3,2-f]quinolin-5-ato(4,10-dimethyl-1,4,7,10-tetraaza-bicyclo[5.5.2]tetradecane)cobalt(III) triflate
  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：

  三氟甲磺酸 、 (4,10-dimethyl-1,4,7,10-tetraaza-bicyclo[5.5.2]tetradecane)(carbonato)cobalt(III) chloride 反应 2.0h， 以65%的产率得到cis-bis(triflato)(4,10-dimethyl-1,4,7,10-tetraaza-bicyclo-[5.5.2]tetradecane)cobalt(III) triflate
  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