Ph₃PAu[S₂CN(ⁱPr)CH₂CH₂OH]

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Ph₃PAu[S₂CN(ⁱPr)CH₂CH₂OH]
• 英文别名: gold(1+);N-(2-hydroxyethyl)-N-propan-2-ylcarbamodithioate;triphenylphosphane
• 化学式: C₂₄H₂₇AuNOPS₂
• 分子量: 637.557
• InChiKey: GZNMVEMLRRBUAQ-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  3.96
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  56.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  三苯基膦氯金 、 以 水 、 丙酮 为溶剂， 反应 1.0h， 以60%的产率得到Ph₃PAu[S₂CN(ⁱPr)CH₂CH₂OH]
  参考文献：
  名称：

  Phosphanegold(I) dithiocarbamates, R3PAu[SC(S)N(iPr)CH2CH2OH] for R = Ph, Cy and Et: Role of phosphane-bound R substituents upon in vitro cytotoxicity against MCF-7R breast cancer cells and cell death pathways

  摘要：

  The synthesis and characterisation of R3PAu[S2CN(Pr-i)CH2CH2OH], for R = Ph (1), Cy (2) and Et (3)4, is reported. Compounds 1-3 are cytotoxic against the doxorubicin-resistant breast cancer cell line, MCF-7R, with 1 exhibiting greater potency and cytotoxicity than either of doxorubicin and cisplatin. Based on human apoptosis PCR-array analysis, caspase activities, DNA fragmentation, cell apoptotic assays, intracellular reactive oxygen species (ROS) measurements and human topoisomerase I inhibition, induction of apoptosis by 1, and necrosis by 2 and 3, are demonstrated, by both extrinsic and intrinsic pathways. Compound 1 activates the p53 gene, 2 activates only the p73 gene, whereas 3 activates both the p53 and p73 genes. Compounds 1 and 3 activate NF-kappa B, and each inhibits topoisomerase I. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.06.038

文献信息

• Phosphanegold(I) dithiocarbamates, R3PAu[SC(S)N(iPr)CH2CH2OH] for R = Ph, Cy and Et: Role of phosphane-bound R substituents upon in vitro cytotoxicity against MCF-7R breast cancer cells and cell death pathways
  作者：Nazzatush Shimar Jamaludin、Zheng-Jie Goh、Yoke Kqueen Cheah、Kok-Pian Ang、Jiun Horng Sim、Chai Hoon Khoo、Zainal Abidin Fairuz、Siti Nadiah Binti Abdul Halim、Seik Weng Ng、Hoi-Ling Seng、Edward R.T. Tiekink

  DOI：10.1016/j.ejmech.2013.06.038

  日期：2013.9

  The synthesis and characterisation of R3PAu[S2CN(Pr-i)CH2CH2OH], for R = Ph (1), Cy (2) and Et (3)4, is reported. Compounds 1-3 are cytotoxic against the doxorubicin-resistant breast cancer cell line, MCF-7R, with 1 exhibiting greater potency and cytotoxicity than either of doxorubicin and cisplatin. Based on human apoptosis PCR-array analysis, caspase activities, DNA fragmentation, cell apoptotic assays, intracellular reactive oxygen species (ROS) measurements and human topoisomerase I inhibition, induction of apoptosis by 1, and necrosis by 2 and 3, are demonstrated, by both extrinsic and intrinsic pathways. Compound 1 activates the p53 gene, 2 activates only the p73 gene, whereas 3 activates both the p53 and p73 genes. Compounds 1 and 3 activate NF-kappa B, and each inhibits topoisomerase I. (C) 2013 Elsevier Masson SAS. All rights reserved.