[(η⁶-p-MeC₆H₄iPr)₂Ru₂Cl₂(μ-SCH₂C₆H₅)₂] | 1355036-37-1

• 英文名称: [(η⁶-p-MeC₆H₄iPr)₂Ru₂Cl₂(μ-SCH₂C₆H₅)₂]
• 英文别名: [(η⁶-p-MeC₆H₄ⁱPr)₂Ru₂Cl₂(μ₂-SCH₂Ph)₂]；((η6-p-cymene)(μ-phenylmethanethiolato)RuCl)2
• CAS: 1355036-37-1
• 化学式: C₃₄H₄₂Cl₂Ru₂S₂
• 分子量: 787.885
• InChiKey: KEMNMKQSNUTKLQ-UHFFFAOYSA-J

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：

  [(η⁶-p-MeC₆H₄iPr)₂Ru₂Cl₂(μ-SCH₂C₆H₅)₂] 、 4-叔丁基苯硫酚 以 乙醇 为溶剂， 反应 15.0h， 以97%的产率得到[(η⁶-p-MeC₆H₄ⁱPr)₂Ru₂(μ₂-SCH₂Ph)₂(μ₂-S-p-C₆H₄^tBu)]⁺Cl^-
  参考文献：
  名称：

  Synthesis, characterization and in vitro anticancer activity of highly cytotoxic trithiolato diruthenium complexes of the type [(η6-p-MeC6H4iPr)2Ru2(μ2-SR1)2(μ2-SR2)]+ containing different thiolato bridges

  摘要：

  A series of cationic dinuclear p-cymene ruthenium complexes containing three thiolato bridges with different substituents at the sulfur atoms, [(eta(6)-p-(MeC6H4Pr)-Pr-i)(2)Ru-2(mu(2)-SR1)(2)(mu(2)-SR2)](+) (R-1 = CH2Ph, R-2 = Ph: 4; R-1 = CH2Ph, R-2 = p-(C6H4Pr)-Pr-i: 5; R-1 = CH2Ph, R-2 = p-(C6H4Bu)-Bu-t: 6; R-1 = CH2Ph, R-2 = p-C6H4OH: 7; R-1 = CH2Ph, R-2 = p-C6H4Br: 8; R-1 = CH2Ph, R-2 = p-C6H4F: 9; R-1 = CH2CH2Ph, R-2 = Ph: 10; R-1 = CH2CH2Ph, R-2 = p-(C6H4Pr)-Pr-i: 11; R-1 = CH2CH2Ph, R-2 = p-(C6H4Bu)-Bu-t: 12; R-1 = CH2CH2Ph, R-2 = p-C6H4OH: 13; R-1 = CH2CH2Ph, R-2 = p-C6H4Br: 14; R-1 = CH2CH2Ph, R-2 = p-C6H4F: 15; R-1 = CH2C6H4-p-Bu-t, R-2 = Ph: 16; R-1 = CH2C6H4-p-Bu-t, R-2 = p-(C6H4Pr)-Pr-i: 17; R-1 = CH2C6H4-p-Bu-t, R-2 = p-(C6H4Bu)-Bu-t: 18; R-1 = CH2C6H4-p-Bu-t, R-2 = p-C6H4OH: 19; R-1 = CH2C6H4-p-Bu-t, R-2 = p-C6H4Br: 20; R-1 = CH2C6H4-p-Bu-t, R-2 = p-C6H4F: 21), have been obtained from the reaction of the neutral dithiolato intermediates [(eta(6)-p-(MeC6H4Pr)-Pr-i)(2)Ru2Cl2(mu(2)-SR1)(2)] (R-1 = CH2Ph: 1; R-1 = CH2CH2Ph: 2; R-1 = CH2C6H4-p-Bu-t: 3) with the corresponding thiophenol (RSH)-S-2. All cationic complexes have been isolated as their chloride salts and fully characterized by spectroscopic and analytical methods. All complexes are highly cytotoxic against human ovarian cancer cells, the IC50 values being in the submicromolar range. The highest activity is shown by complex 6 with IC50 values of 48 nM against the A2780 cell line and 42 nM against the cisplatin-resistant line A2780cisR. This family of cationic trithiolato complexes belongs to the most cytotoxic ruthenium compounds ever reported. The catalytic activity selected representatives for the oxidation of glutathione (GSH) to GSSG has been investigated by NMR spectroscopy. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2013.04.049
• 作为产物：
  描述：

  [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂ 、 苄硫醇 以 乙醇 为溶剂， 生成 [(η⁶-p-MeC₆H₄iPr)₂Ru₂Cl₂(μ-SCH₂C₆H₅)₂]
  参考文献：
  名称：

  表征双核硫氰酸盐桥联的芳烃钌络合物对弓形虫的活性。

  摘要：

  最初设计为抗癌剂的18种双核巯基桥连的芳烃钌配合物（1种单硫醇化合物，4种二硫醇化合物和13种三硫醇化合物）对人包皮成纤维细胞（HFF）宿主上生长的apicomplexan寄生虫弓形虫的体外作用被研究了。在浓度为250 nM或更低时，某些三硫latolato化合物显示出抗寄生虫功效。其中，复合物1和复合物2分别以34％和62 nM的50％抑制浓度（IC50s）抑制刚地弓形虫的增殖，并且在200μM或更高剂量下它们不影响HFF，导致选择性指数> 23,000 。对于刚地弓形虫，复合物9的IC50为1.2 nM，而对于HFF，复合物9的IC50为5μM以上。透射电子显微镜在治疗的早期阶段检测到寄生虫线粒体基质中的超微结构改变，随后速殖子的破坏更为明显。但是，在250 nM下施用15天的这三种化合物均无杀虫作用。通过使用配合物9偶联至环氧活化的Sepharose的亲和色谱，然后进行质谱分析，刚地

  DOI：

  10.1128/aac.01031-17

文献信息

• Water-soluble trithiolato-bridged dinuclear ruthenium(II) and osmium(II) arene complexes with bisphosphonate functionalized ligands as anticancer organometallics
  作者：Christoph A. Riedl、Alexander Rosner、Sophia Harringer、Philipp Salomon、Michaela Hejl、Michael A. Jakupec、Wolfgang Kandioller、Bernhard K. Keppler

  DOI：10.1016/j.jinorgbio.2021.111618

  日期：2021.12

  trithiolato-bridged dinuclear ruthenium(II) and osmium(II) arene complexes bearing one to three bisphosphonate-benzylmercaptane derived ligands. In addition to improved aqueous solubility the high affinity of bisphosphonates towards apatite structures found in bone and bone metastases may grant selective targeting properties to functionalized organometallics. The complex stabilities and hydroxyapatite binding

  三硫醇桥联双核钌 (II) 配合物 [Ru 2 ( p -cym) 2 (SR) 3 ]Cl ( p -cym =  p- 伞花烃，R = 苄基衍生物）被认为是最具细胞毒性的金属 (II) 芳烃抗肿瘤剂，但通常因其在水性介质中的溶解度差而受到限制。因此，我们设计了用于模块化两步络合过程的双膦酸盐官能化配体，以合成六种三硫醇桥联的双核钌 (II) 和锇 (II) 芳烃配合物，这些配合物带有一到三个双膦酸盐-苄硫醇衍生的配体。除了提高水溶性外，双膦酸盐对骨和骨转移中发现的磷灰石结构的高亲和力可以赋予功能化有机金属选择性靶向特性。复合物稳定性和羟基磷灰石结合行为通过紫外/可见光谱测定。双膦酸盐官能化降低抗增殖活性由于候选药物的亲脂性不同，这与较低的细胞积累有关。
• Monothiolato‐Bridged Dinuclear Arene Ruthenium Complexes: The Missing Link in the Reaction of Arene Ruthenium Dichloride Dimers with Thiols
  作者：David Stíbal、Bruno Therrien、Federico Giannini、Lydia E. H. Paul、Julien Furrer、Georg Süss‐Fink

  DOI：10.1002/ejic.201402754

  日期：2014.12

  with R = CH2C6H5 (1), p-CH2C6H4NO2 (2), C10H15 (3), m-9-B10C2H11 (4) were synthesized by treating [(η6-p-MeC6H4iPr)2Ru2Cl2(μ-Cl)2] with the corresponding thiols RSH. The reaction of p-cymene ruthenium dichloride dimer with thiols is well known to give the cationic trithiolato complexes [(η6-p-MeC6H4iPr)2Ru2(μ-SR)3]+, but recently the intermediary dithiolato complexes [(η6-p-MeC6H4iPr)2Ru2Cl2(μ-SR)2]

  单硫醇络合物 [(η6-p-MeC6H4iPr)2Ru2Cl2(μ-Cl)(μ-SR)] 与 R = CH2C6H5 (1), p-CH2C6H4NO2 (2), C10H15 (3), m-9-B10C2H11 (4) ) 是通过用相应的硫醇 RSH 处理 [(η6-p-MeC6H4iPr)2Ru2Cl2(μ-Cl)2] 合成的。众所周知，对伞花烃二氯化钌二聚体与硫醇反应生成阳离子三硫醇络合物 [(η6-p-MeC6H4iPr)2Ru2(μ-SR)3]+，但最近中间体二硫醇络合物 [(η6-p-在某些情况下，MeC6H4iPr)2Ru2Cl2(μ-SR)2] 也可以被分离和表征。现在观察到的 monothiolato 复合物 1-4 代表了 trithiolato 复合物逐步形成中的缺失环节。配合物 1 和 2 的单晶 X 射线结构分析表明，两个钌原子被氯配体和硫醇基配体桥接，没有金属 -
• Thiolato‐Bridged Arene–Ruthenium Complexes: Synthesis, Molecular Structure, Reactivity, and Anticancer Activity of the Dinuclear Complexes [(arene) ₂ Ru ₂ (SR) ₂ Cl ₂ ]
  作者：Anne‐Flore Ibao、Michaël Gras、Bruno Therrien、Georg Süss‐Fink、Olivier Zava、Paul J. Dyson

  DOI：10.1002/ejic.201101057

  日期：2012.3

  the two thiolato ligands without a metalmetal bond. The neutral dithiolato complexes[(arene)2Ru2(SR)2Cl2] (13) are intermediates in the formation of the cationic trithiolato complexes [(arene)2Ru2(SR)3]+ (57). Of the new [(arene)2Ru2(SR)2Cl2] complexes, derivative 2 is highly cytotoxic against human ovarian cancer cells, with IC50 values of 0.20 mu M for the A2780 cell line and 0.31 for the cisplatin-resistant

  用硫醇 RSH 处理二氯化芳钌二聚体以产生 [(芳烃)2Ru2(SR)3]+ 类型的阳离子三硫代络合物，显示通过中性硫代络合物 [(芳烃)2Ru2(SR)2Cl2]，已分离并表征芳烃 = p-MeC6H4iPr 和 R = CH2Ph (1)、CH2CH2Ph (2)、CH2C6H4-p-tBu (3) 和 C6H11 (4)。对叔丁基苄基衍生物 3 的单晶 X 射线结构分析表明，两个钌原子由两个硫醇基配体桥接，没有金属金属键。中性二硫代络合物[(芳烃)2Ru2(SR)2Cl2](13)是形成阳离子三硫代络合物[(芳烃)2Ru2(SR)3]+(57)的中间体。在新的 [(arene)2Ru2(SR)2Cl2] 复合物中，衍生物 2 对人卵巢癌细胞具有高度细胞毒性，IC50 值为 0。