[(η5-pentamethylcyclopentadienyl)Ir(2-phenylquinoline(1-))Cl] | 1326301-04-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: [(η5-pentamethylcyclopentadienyl)Ir(2-phenylquinoline(1-))Cl]
• 英文别名: iridium(3+);1,2,3,4,5-pentamethylcyclopenta-1,3-diene;2-phenylquinoline;chloride
• CAS: 1326301-04-5
• 化学式: C₂₅H₂₅ClIrN
• 分子量: 567.153
• InChiKey: BGSQSFABWWENIN-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  3.65
• 重原子数：
  28
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  氘代甲醇 、 [(η5-pentamethylcyclopentadienyl)Ir(2-phenylquinoline(1-))Cl] 、 重水 以 氘代甲醇 、 重水 为溶剂， 生成 [(η5-pentamethylcyclopentadienyl)Ir(2-phenylquinoline(1-))(D2O)](1+) 、 ([(η5-pentamethylcyclopentadienyl)Ir]2(μ-OD)3)(1+)
  参考文献：
  名称：

  Organometallic Iridium(III) Cyclopentadienyl Anticancer Complexes Containing C,N-Chelating Ligands

  摘要：

  Organometallic Ir(III) cyclopentadienyl complexes [(eta(5)-Cp(x))Ir(C((sic))N)Cl] {Cp(x) = Cp*, C((sic))N = 2-(p-tolyl)pyridine (1), 2-phenylquinoline (2), 2-(2,4-difluorophenyl)pyridine (3), Cp(x) = tetramethyl(phenyl)cyclopentadienyl (Cp(xph)), C((sic))N = 2-phenylpyridine (4), and Cp(x) = tetramethyl(biphenyl)cyclopentadienyl (C(pxbiph)), C((sic))N = 2-phenylpyridine (5)} have been synthesized and characterized. The X-ray crystal structures of 2 and 5 have been determined and show typical "piano-stool" geometry. All the complexes hydrolyzed rapidly in aqueous solution (< 5 min) even at 278 K. The plc values of the aqua adducts 1A-5A are in the range 8.31-8.87 and follow the order 1A > 2A > 4A > 5A approximate to 3A. Hydroxo-bridged dimers {[eta(5)-Cp(x))Ir](2)(mu-OD)(3)}(+) (Cp(x) = Cp*, 6; Cp(xph), 7; Cp(xbiph), 8) are readily formed during pH titrations at ca. pH 8.7. Complexes I and 3-5 bind strongly to 9-ethylguanine (9-EtG) moderately strongly to 9-methyladenine (9-MeA), and hence preferentially to 9-EtG when in competition with 9-MeA. The extent of guanine and adenine binding to complex 2 was significantly lower for both purines due to steric hindrance from the chelating ligand. All complexes showed potent cytotoxicity, with IC(50) values ranging from 6.5 to 0.7 mu M toward A2780 human ovarian cancer cells. Potency toward these cancer cells increased with additional phenyl substitution on Cp*, Cp(xbiph) > Cp(xph) > Cp*, Cp(xbiph) with complex 5 exhibited submicromolar activity (2X as active as cisplatin). These data demonstrate how the aqueous chemistry, nucleobase binding, and anticancer activity of C,N-bound Ir(III) cyclopentadienyl complexes can be controlled and fine-tuned by the modification of the chelating and cyclopentadienyl ligands.

  DOI：

  10.1021/om2005468
• 作为产物：
  描述：

  bis[dichloro(pentamethylcyclopentadienyl)iridium(III)] 、 2-苯基喹啉 在 sodium acetate 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以75%的产率得到[(η5-pentamethylcyclopentadienyl)Ir(2-phenylquinoline(1-))Cl]
  参考文献：
  名称：

  [EN] NOVEL IRIDIUM/RHODIUM ANTI-CANCER COMPOUNDS
  [FR] NOUVEAUX COMPOSÉS ANTICANCÉREUX CONTENANT DE L'IRIDIUM/RHODIUM

  摘要：

  本发明涉及用作细胞毒性物质，如抗癌药物的新型含铱和/或铑配合物，还提供了一种制备所述化合物的方法。

  公开号：

  WO2011148124A1