chlorido(8-quinolinolato-k²N,O)(η⁶-p-cymene)osmium(II) | 934755-79-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: chlorido(8-quinolinolato-k²N,O)(η⁶-p-cymene)osmium(II)
• 英文别名: [(η6-p-cymene)Os(8-hydroxyquinolinato)Cl]；[(η6-p-cym)Os(oxine)Cl]；[(η6-p-cymene)(8-hydroxyquinoline(-1H))OsCl]；[(η6-p-cym)Os(quin)Cl]；1-methyl-4-propan-2-ylbenzene;osmium(2+);quinolin-8-olate;chloride
• CAS: 934755-79-0
• 化学式: C₁₉H₂₀ClNOOs
• 分子量: 504.027
• InChiKey: PELSLZWKJPJITH-UHFFFAOYSA-L

计算性质

• 辛醇/水分配系数(LogP)：
  1.43
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  36
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  chlorido(8-quinolinolato-k²N,O)(η⁶-p-cymene)osmium(II) 、 重水 以 重水 为溶剂， 生成 [(η6-p-cymene)Os(8-hydroxyquinolinato)(OD2)](1+)
  参考文献：
  名称：

  Tuning the Hydrolytic Aqueous Chemistry of Osmium Arene Complexes with N,O-Chelating Ligands to Achieve Cancer Cell Cytotoxicity

  摘要：

  Potential biological and medical applications of organometallic complexes are hampered by a lack of knowledge of their aqueous solution chemistry. We show that the hydrolytic and aqueous solution chemistry of half-sandwich Os-II arene complexes of the type [(eta(6)-arene)Os(XY)Cl] can be tuned with XY chelating ligands to achieve cancer cell cytoxicity comparable to carboplatin. Complexes containing arene = p-cymene, XY = N,O-chelating ligands glycinate (1), l-alaninate (2), alpha-aminobutyrate (3), beta-alaninate (4), picolinate (5), or 8-hydroxyquinolinate (7) were synthesized. Although, 1-4 and 4 hydrolyzed rapidly (< min), complexes with pi-acceptor pyridine as N-donor and carboxylate as O-donor (5 and 6) hydrolyzed much more slowly (t(1/2) = 0.20 and 0.52 h, 298 K). The aqua picolinate complexes were more acidic (pK(a)* = 6.67, 6.33) than the other aqua adducts (pK(a)* = 7.17-7.71). At biological test concentrations (micromolar), the chelating ligands dissociated from complexes \1-4 to give the inert hydroxo-bridged dinuclear species [(eta(6)-arene)Os(mu-OH)(3)Os(eta(6)-arene)](+) (8), and these complexes were inactive toward human lung A549 and ovarian A2780 cancer cells. In contrast, 5-7 were cytotoxic, especially 6 (IC50 values of 8 and 4.2 mu M). The X-ray structures of 9-ethylguanine, [(eta(6)-p-cym)Os(pico)(9EtG-N7)]PF6, and 9-ethyladenine, [(eta(6)-p-cym)Os(pico)(9EtA-N7)]PF6, adducts of 5 are reported (the first reported for G or A adducts of Os-II). Crystals of the 9EtA complex contain homoadenine base pairing. The 9EtG adduct in particular exhibits remarkable aqueous kinetic stability. This work shows how the rational control of chemical reactivity (hydrolysis, acidity, formation of hydroxo-bridged dinuclear species) can allow the design of cytotoxic anticancer Os-II arene complexes.

  DOI：

  10.1021/ja068335p
• 作为产物：
  描述：

  8-羟基喹啉 、 [osmium(II)dichloride(η6-p-cymene)]2 在 NaOCH₃ 作用下， 以 甲醇 为溶剂， 以84%的产率得到chlorido(8-quinolinolato-k²N,O)(η⁶-p-cymene)osmium(II)
  参考文献：
  名称：

  具有高抗增殖活性的水溶性混合配体钌（II）和O（II）芳烃配合物

  摘要：

  钌的合成（II）和锇（II）芳烃通式的配合物[（η 6 - p -cymene）M（喔星）（Hazole）] X，其中M =钌，锇; oxine =去质子化的8-羟基喹啉，Hazole =唑杂环，即吡唑（Hpz），吲唑（Hind），咪唑（Him），苯并咪唑（Hbzim）或5,6-二甲基苯并咪唑（Hdmbzim）；X = CF 3 SO 3 -，PF 6 -，或Cl -据报道，结合了目前正在临床开发中的金属基配合物所涉及的配体。这些化合物已通过元素分析，ESI质谱，光谱学（IR，UV-vis，NMR）和X射线晶体学进行了全面表征。进行这些配合物的合成是为了在水溶性和亲脂性之间取得平衡。钌（II）和（II）化合物在肿瘤细胞系CH1和SW480中表现出出色的细胞毒性作用，IC 50值在3.3至9.4μM之间。如所预期的，这些化合物是水溶性的，在水介质中没有水解或配体交换的迹象，这使其成为值得进一步开发的候选化合物。的配合物[（η

  DOI：

  10.1021/om800774t

文献信息

• Hydroxyquinoline-derived anticancer organometallics: Introduction of amphiphilic PTA as an ancillary ligand increases their aqueous solubility
  作者：William D.J. Tremlett、Kelvin K.H. Tong、Tasha R. Steel、Sanam Movassaghi、Muhammad Hanif、Stephen M.F. Jamieson、Tilo Söhnel、Christian G. Hartinger

  DOI：10.1016/j.jinorgbio.2019.110768

  日期：2019.10

  Organometallic compounds based on bioactive ligand systems have shown promising antiproliferative properties. The use of 8-hydroxyquinoline and its derivatives as bioactive ligands resulted in organometallic complexes with potent anticancer activity, but they lack aqueous solubility for further development. We report here the preparation of a series of MII/III(cym/Cp*)Cl complexes (η6-p-cymene (cym):

  基于生物活性配体系统的有机金属化合物已显示出令人期待的抗增殖特性。使用8-羟基喹啉及其衍生物作为生物活性配体可产生具有有效抗癌活性的有机金属配合物，但它们缺乏水溶性，无法进一步开发。我们在这里报告的一系列M的制备II / III（CYM / CP *）氯配合物（η 6 - p -cymene（CYM）：M =茹，锇;η 5-五甲基环戊二烯基（CP *）：M = Rh，Ir）与羟基喹啉衍生的共配体，并在随后的步骤中用氯代配体取代两亲的1,3,5-triaza-7-phosphatritricyclo- [3.3.1.1]癸烷（PTA）。溶解度研究表明，引入的PTA配体显着改善了所有配合物的水溶性。该络合物在水溶液和DMSO溶液中至少3 d稳定。如对复合物的这种修饰所预期的那样，较高的溶解度导致癌细胞中的细胞毒性显着降低。其抗增殖活性仍比RAPTA-C [Ru（cym）（PTA）Cl]强，但已
• WO2008/17855
  申请人：——

  公开号：——

  公开（公告）日：——