1,2-bis(di-1-methylimidazol-2-ylphosphino)ethane | 1242167-02-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1,2-bis(di-1-methylimidazol-2-ylphosphino)ethane
• 英文别名: bis(di-1-methylimidazol-2-ylphosphino)ethane；1,2-bis(di(N-methylimidazol-2-yl)phosphino)ethane；2-dimpeNMe；2-Bis(1-methylimidazol-2-yl)phosphanylethyl-bis(1-methylimidazol-2-yl)phosphane；2-bis(1-methylimidazol-2-yl)phosphanylethyl-bis(1-methylimidazol-2-yl)phosphane
• CAS: 1242167-02-7
• 化学式: C₁₈H₂₄N₈P₂
• 分子量: 414.39
• InChiKey: PFIOPDUDLLBZBF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  71.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,2-bis(di-1-methylimidazol-2-ylphosphino)ethane 在 水 、 双氧水 作用下， 以 乙醇 为溶剂， 反应 8.0h， 以38 mg的产率得到P,P'-bis(1-methylimidazol-2-yl)ethylenediphosphinic acid
  参考文献：
  名称：

  Synthesis, X-ray crystal structure and cytotoxicity of a new tetranuclear ruthenium arene complex

  摘要：

  The tetranuclear ruthenium arene compound [(cym)(4)Ru-4(2)Cl-6]Cl-2 (3) (cym = eta(6)-p-cymene, 2 = 1,2-bis (di-N-methylimidazol-2-ylphosphino)ethane) was prepared and characterised by one- and two-dimensional NMR techniques. Its cytotoxicity against four different cell lines was determined and, with an approximate IC50 of > 100 mu M 3 can be regarded as non-toxic. Its partition coefficient in n-octanol/water (log D-7.4) was also determined. The structures of complex 3 as well as of the related compound [(cym)(2)Ru-2(4)Cl-2]Cl-2 (5) (4 = 1,2-bis(di-N-methylimidazol-2-ylphosphino)ethane dioxide) were determined by single crystal structure analysis. Upon oxidation in protic solvents, ligand 2 shows P-C bond cleavage reactions to yield P,P'-bis(N-methylimidazol-2-yl)ethylene diphosphinic acid (6). (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2010.10.042
• 作为产物：
  描述：

  1,2-双(二氯磷基)-乙烷 、 三甲基-(1-甲基咪唑-2-基)硅烷 生成 1,2-bis(di-1-methylimidazol-2-ylphosphino)ethane
  参考文献：
  名称：

  Gold(i) complexes of water-soluble diphos-type ligands: Synthesis, anticancer activity, apoptosis and thioredoxin reductase inhibition

  摘要：

  研究人员制备了咪唑和噻唑二磷配体的金（I）配合物，并对其作为化疗药物的潜力进行了研究。根据所用配体和反应条件的不同，可以得到[L(AuCl)2]和[L2Au]X（X = Cl，PF6）配合物。使用的配体是带有偶氮取代基 R2P(CH2)2PR2 {R = 1-甲基咪唑-2-基（1），1-甲基苯并咪唑-2-基（4）、噻唑-2-基 (5) 和苯并噻唑-2-基 (6)} 以及新型配体 RPhP(CH2)2PRPh {R = 1-甲基咪唑-2-基 (3)} 和 R2P(CH2)3PR2 {R = 1-甲基咪唑-2-基 (2)}。评估了这些配合物对三种人类癌细胞系和一种大鼠肝癌细胞系的细胞毒性活性，并将其与化合物的亲脂性联系起来。具有中等亲油性（logD7.4 = 0.21 和 0.25）的四面体金配合物 [(3)2Au]PF6 和 [(5)2Au]PF6 在不同细胞系中显示出显著的细胞毒性活性。这两种化合物都能诱导细胞凋亡并抑制硫代氧化还原酶和谷胱甘肽还原酶。

  DOI：

  10.1039/c1dt10368g

文献信息

• Novel multitopic diphos-type ligands.
  作者：Peter C. Kunz、Corinna Wetzel、Melanie Bongartz、Anna Louisa Noffke、Bernhard Spingler

  DOI：10.1016/j.jorganchem.2010.04.028

  日期：2010.7

  Seven novel imidazole and thiazole derivatives of diphos-type ligands are presented. They are of the general structure R(2)P(CH(2))(2)PR(2), where R is imidazol-2-yl (1), 1-methylimidazol-2-yl (2), 1-methyl-benzimidazol-2-yl (3), 1-methylimidazol-5-yl (4), 2-isopropylimidazol-4(5)-yl (5), thiazol-2-yl (6), benzothiazol-2-yl (7), thiazol-4-yl (8) or thiazol-5-yl (9). Syntheses involved direct metallation or halogen-metal exchange reactions. Their solubility, especially in aqueous solution, is strongly dependent on the nature of the substituents as is their partition coefficient log D. The crystal structures of compounds 2, 3, 7a and 9 as well as the structure of the rhodium complex [(2)(2)Rh(2)Cl(2)]Cl(2) (10) have been determined. (C) 2010 Elsevier B. V. All rights reserved.
• Gold(i) complexes of water-soluble diphos-type ligands: Synthesis, anticancer activity, apoptosis and thioredoxin reductase inhibition
  作者：Corinna Wetzel、Peter. C. Kunz、Matthias U. Kassack、Alexandra Hamacher、Philip Böhler、Wim Watjen、Ingo Ott、Riccardo Rubbiani、Bernhard Spingler

  DOI：10.1039/c1dt10368g

  日期：——

  Gold(I) complexes of imidazole and thiazole-based diphos type ligands were prepared and their potential as chemotherapeutics investigated. Depending on the ligands employed and the reaction conditions complexes [L(AuCl)2] and [L2Au]X (X = Cl, PF6) are obtained. The ligands used are diphosphanes with azoyl substituents R2P(CH2)2PR2 R = 1-methylimidazol-2-yl (1), 1-methylbenzimidazol-2-yl (4), thiazol-2-yl (5) and benzthiazol-2-yl (6)} as well as the novel ligands RPhP(CH2)2PRPh R = 1-methylimidazol-2-yl (3)} and R2P(CH2)3PR2 R = 1-methylimidazol-2-yl (2)}. The cytotoxic activity of the complexes was assessed against three human cancer cell lines and a rat hepatoma cell line and correlated to the lipophilicity of the compounds. The tetrahedral gold complexes [(3)2Au]PF6 and [(5)2Au]PF6 with intermediate lipophilicity (logD7.4 = 0.21 and 0.25) showed significant cytotoxic activity in different cell lines. Both compounds induce apoptosis and inhibit the enzymes thioredoxin reductase and glutathione reductase.

  研究人员制备了咪唑和噻唑二磷配体的金（I）配合物，并对其作为化疗药物的潜力进行了研究。根据所用配体和反应条件的不同，可以得到[L(AuCl)2]和[L2Au]X（X = Cl，PF6）配合物。使用的配体是带有偶氮取代基 R2P(CH2)2PR2 R = 1-甲基咪唑-2-基（1），1-甲基苯并咪唑-2-基（4）、噻唑-2-基 (5) 和苯并噻唑-2-基 (6)} 以及新型配体 RPhP(CH2)2PRPh R = 1-甲基咪唑-2-基 (3)} 和 R2P(CH2)3PR2 R = 1-甲基咪唑-2-基 (2)}。评估了这些配合物对三种人类癌细胞系和一种大鼠肝癌细胞系的细胞毒性活性，并将其与化合物的亲脂性联系起来。具有中等亲油性（logD7.4 = 0.21 和 0.25）的四面体金配合物 [(3)2Au]PF6 和 [(5)2Au]PF6 在不同细胞系中显示出显著的细胞毒性活性。这两种化合物都能诱导细胞凋亡并抑制硫代氧化还原酶和谷胱甘肽还原酶。
• Synthesis, X-ray crystal structure and cytotoxicity of a new tetranuclear ruthenium arene complex
  作者：Anna Louisa Noffke、Melanie Bongartz、Wim Wätjen、Philip Böhler、Bernhard Spingler、Peter C. Kunz

  DOI：10.1016/j.jorganchem.2010.10.042

  日期：2011.3

  The tetranuclear ruthenium arene compound [(cym)(4)Ru-4(2)Cl-6]Cl-2 (3) (cym = eta(6)-p-cymene, 2 = 1,2-bis (di-N-methylimidazol-2-ylphosphino)ethane) was prepared and characterised by one- and two-dimensional NMR techniques. Its cytotoxicity against four different cell lines was determined and, with an approximate IC50 of > 100 mu M 3 can be regarded as non-toxic. Its partition coefficient in n-octanol/water (log D-7.4) was also determined. The structures of complex 3 as well as of the related compound [(cym)(2)Ru-2(4)Cl-2]Cl-2 (5) (4 = 1,2-bis(di-N-methylimidazol-2-ylphosphino)ethane dioxide) were determined by single crystal structure analysis. Upon oxidation in protic solvents, ligand 2 shows P-C bond cleavage reactions to yield P,P'-bis(N-methylimidazol-2-yl)ethylene diphosphinic acid (6). (C) 2010 Elsevier B.V. All rights reserved.