bis(triethylphosphine)digold(I) 3-(2-thienyl)-2-sulfanylpropenoate | 1039404-64-2

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: bis(triethylphosphine)digold(I) 3-(2-thienyl)-2-sulfanylpropenoate
• CAS: 1039404-64-2
• 化学式: C₁₉H₃₄Au₂O₂P₂S₂
• 分子量: 814.49
• InChiKey: KXEZTRZFBPZYHT-UHFFFAOYSA-L

计算性质

• 辛醇/水分配系数(LogP)：
  5.44
• 重原子数：
  27.0
• 可旋转键数：
  13.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  40.13
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  bis(triethylphosphine)digold(I) 3-(2-thienyl)-2-sulfanylpropenoate 在 DMSO-d6 作用下， 以 氘代二甲亚砜 为溶剂， 生成 bis(triethylphosphine)gold(I)(1+) 、 triethylphosphinegold(I) (3-(2-thienyl)-2-sulfanylpropenoate(1-))
  参考文献：
  名称：

  Synthesis, Structural Characterization, and Antiinflammatory Activity of Triethylphosphinegold(I) Sulfanylpropenoates of the Type [(AuPEt₃)₂xspa] [H₂xspa = 3-(Aryl)-2-sulfanylpropenoic acid]: an (H₂O)₆ Cluster in the Lattice of the Complexes [(AuPEt₃)₂xspa]·3H₂O

  摘要：

  Gold complexes of the type [(AuPEt3)(2)xspa] were prepared by reacting AuPEt3Cl in basic media with the 3-(aryl)-2-sulfanylpropenoic acids H(2)xspa [x = p, Clp, -o-mp, -p-mp, -o-hp, -p-hp, diBr-o-hp, f, t, -o-py; p = 3-phenyl, Clp = 3-(2-chlorophenyl)-, -o-mp = 3-(2-methoxyphenyl)-, -p-mp = 3-(4-methoxyphenyl)-, -o-hp = 3-(2-hydroxyphenyl)-, -p-hp = 3-(4-hydroxyphenyl)-, -diBr-o-hp = 3-(3,5- dibromo-2-hydroxyphenyl)-, t = 3-(2-furyl)-, t = 3-(2-thienyl)-, -o-py = 3-(2-pyridyl); spa = 2-sulfanylpropenoato], and 2-cyclopentylidene-2-sulfanylacetic acid (H(2)cpa). The complexes were characterized by spectroscopic methods (IR, H-1, C-13 and P-31 NMR) and mass spectrometry, and the complexes [(AuPEt3)(2)pspa]center dot 3H(2)O, [(AuPEt3)(2)-p-hpspa]center dot 3H(2)O, [(AuPEt3)(2)tspa)]center dot 3H(2)O, and [(AuPEt3)(2)-o-hpspa] by X-ray diffractometry. The crystals of the first three complexes contain (H2O)(6) clusters hydrogen bonded to [(AuPEt3)2xspa]2 dimer units, whereas in the -o-hpspa derivative the hydrogen bonds are between the monomer [(AuPEt3)2-o-hpspa] units. The antiinflammatory activity of the complexes against plantar edema induced by carrageenan in rats is generally significant, with the values for the o-hpspa and tspa derivatives being particularly high.

  DOI：

  10.1021/ic800314p
• 作为产物：
  描述：

  氯(三乙基膦)金(I) 、 3-(2-thienyl)-2-sulfanylpropenoic acid 在 NaOH 作用下， 以 甲醇 、 水 为溶剂， 以74%的产率得到bis(triethylphosphine)digold(I) 3-(2-thienyl)-2-sulfanylpropenoate
  参考文献：
  名称：

  Synthesis, Structural Characterization, and Antiinflammatory Activity of Triethylphosphinegold(I) Sulfanylpropenoates of the Type [(AuPEt₃)₂xspa] [H₂xspa = 3-(Aryl)-2-sulfanylpropenoic acid]: an (H₂O)₆ Cluster in the Lattice of the Complexes [(AuPEt₃)₂xspa]·3H₂O

  摘要：

  Gold complexes of the type [(AuPEt3)(2)xspa] were prepared by reacting AuPEt3Cl in basic media with the 3-(aryl)-2-sulfanylpropenoic acids H(2)xspa [x = p, Clp, -o-mp, -p-mp, -o-hp, -p-hp, diBr-o-hp, f, t, -o-py; p = 3-phenyl, Clp = 3-(2-chlorophenyl)-, -o-mp = 3-(2-methoxyphenyl)-, -p-mp = 3-(4-methoxyphenyl)-, -o-hp = 3-(2-hydroxyphenyl)-, -p-hp = 3-(4-hydroxyphenyl)-, -diBr-o-hp = 3-(3,5- dibromo-2-hydroxyphenyl)-, t = 3-(2-furyl)-, t = 3-(2-thienyl)-, -o-py = 3-(2-pyridyl); spa = 2-sulfanylpropenoato], and 2-cyclopentylidene-2-sulfanylacetic acid (H(2)cpa). The complexes were characterized by spectroscopic methods (IR, H-1, C-13 and P-31 NMR) and mass spectrometry, and the complexes [(AuPEt3)(2)pspa]center dot 3H(2)O, [(AuPEt3)(2)-p-hpspa]center dot 3H(2)O, [(AuPEt3)(2)tspa)]center dot 3H(2)O, and [(AuPEt3)(2)-o-hpspa] by X-ray diffractometry. The crystals of the first three complexes contain (H2O)(6) clusters hydrogen bonded to [(AuPEt3)2xspa]2 dimer units, whereas in the -o-hpspa derivative the hydrogen bonds are between the monomer [(AuPEt3)2-o-hpspa] units. The antiinflammatory activity of the complexes against plantar edema induced by carrageenan in rats is generally significant, with the values for the o-hpspa and tspa derivatives being particularly high.

  DOI：

  10.1021/ic800314p

文献信息

• Mono and dinuclear phosphinegold(I) sulfanylcarboxylates: Influence of nuclearity and substitution of PPh 3 for PEt 3 on cytotoxicity
  作者：Elena Barreiro、José S. Casas、María D. Couce、Agustín Sánchez、Angeles Sánchez-Gonzalez、José Sordo、Ezequiel M. Vázquez-López

  DOI：10.1016/j.jinorgbio.2014.05.010

  日期：2014.9

  Gold complexes of the type [Au(PEt3)(Hxspa)] were prepared by reacting triethylphosphinegold(I) chloride in ethanol/water (8:1) with the 3-(aryl)-2-sulfanylpropenoic acids H(2)xspa [x = p = 3-phenyl-; f = 3-(2-furyl)-; t = 3-(2-thienyl)-; py = 3-(2-pyridyl); Clp = 3-(2-Chlorophenyl)-; -o-mp = 3-(2-methoxyphenyl)-; -p-mp = 3-(4-methoxyphenyl)-; -o-hp = 3-(2-hydroxyphenyl)-; -p-hp = 3-(4-hydroxyphenyl)-; -diBr-o-hp = 3-(3,5-dibromo-2-hidroxyphenyl-); spa = 2-sulfanylpropenoato] or 2-cyclopentylidene-2-sulfanylacetic acid (H(2)cpa) and KOH in a 1:1:1 mole ratio. The compounds were characterized by IR spectroscopy and FAB mass spectrometry and by H-1, C-13 and P-31 NMR spectroscopy. The in vitro antitumor activity of these and of the previously described dinuclear [(AuPEt3)(2)(xspa)] complexes against the HeLa-229, A2780 and A2780cis cell lines was determined and compared with those of the analogous PPh3 complexes. The results show that the substitution of the PPh3 ligand by PEt3 is particularly effective in increasing the cytotoxicity of the dinuclear [(AuPR3)(2)(xspa)] complexes, giving rise to compounds that are significantly more active than cisplatin against the aforementioned cell lines. In addition, and as a preliminary test for nephrotoxicity, the cytotoxicity of the most active compounds against the normal renal LCC-PK1 cell line was evaluated and compared with that of cisplatin. (C) 2014 Elsevier Inc. All rights reserved.