1-(2-Sulfanylethyl)piperidin-4-one | 299187-65-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 1-(2-Sulfanylethyl)piperidin-4-one
• CAS: 299187-65-8
• 化学式: C₇H₁₃NOS
• 分子量: 159.252
• InChiKey: RXCPBKYUVKVVDW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  21.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(2-Sulfanylethyl)piperidin-4-one 、 4-氯-7-硝基苯并-2-氧杂-1,3-二唑 在 potassium hydroxide 作用下， 以 aq. phosphate buffer 、 乙醇 为溶剂， 反应 24.0h， 以51%的产率得到1-(2-((7-nitrobenzo[c][1,2,5]oxadiazol-4-yl)thio)ethyl)piperidin-4-one
  参考文献：
  名称：

  Synthesis and structure–activity relationship of new cytotoxic agents targeting human glutathione-S-transferases

  摘要：

  The 6((7-nitrobenzo[c][1,2,5]oxadiazol-4-yl)thio)hexan-1-ol (NBDHEX, 1), a "suicide inhibitor" of the glutathione-S-transferase GSTP1-1, showed pro-apoptotic properties in tumor cells, but in vivo studies were limited by poor bioavailability and high affinity towards GSTM2-2, expressed in many non-cancerous tissues. Here we describe the synthesis and biological characterization of new 1 analogs (2-40), in which the hydroxyhexyl portion at the C4-sulfur atom has been replaced with phenyl-containing moieties as well as substituted alkyl chains. Some of the new compounds displayed 10-100 times increased water-solubility (8, 11, 17, 26-28, 34, 35), and most of them showed higher GSTP1-1 selectivity (2-20, 23-26, 31-33, 35) than 1. The presence of a phenyl ring with polar substituents is in general associated, with some exceptions (23, 24) to low cytotoxicity in osteosarcoma U-2OS cells. Differently, some alkyl derivatives possess cytotoxicity comparable (26, 34,35) or higher (30, 32) than 1. Among the novel compounds, selected ones (26, 27, 34, and 35) deserve further investigation for their anticancer potential. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.10.033

文献信息

• Neutral ‘3 + 1’ mixed-ligand oxorhenium(V) complexes with tridentate [S,N,S] chelates and aminoalkanethiols: synthesis, characterization and structure determination ‡
  作者：Matthias Friebe、Hartmut Spies、Wilhelm Seichter、Peter Leibnitz、Bernd Johannsen

  DOI：10.1039/b001600o

  日期：——

  ‘3 + 1’ Oxorhenium(V) complexes [ReO(SN(R′)S)(SR)] (R′ = Me, Et, Pr or Bu; SR = aminoalkane thiolate) have been synthesized by ligand exchange at trans-trichloromonooxo-bis(triphenylphosphine)rhenium(V) with a mixture of HSN(R′)SH and RSH in alkaline methanolic solution. The complexes were purified by column chromatography and characterized by elemental analysis, mass and IR spectroscopy and for selected compounds by 1H NMR spectroscopy. The structures of those complexes have been determined by X-ray diffraction analysis and revealed a change in the co-ordination geometry from square pyramidal to trigonal bipyramidal, depending on the chelating (SN(R′)S) moiety. The alkyl group (R′) was found to be arranged “syn” to the oxorhenium group.

  �3+1�氧铼(V)络合物[ReO(SN(R�2)S)(SR)]（R�2=Me、Et、Pr或Bu；SR=氨基烷硫醇盐）通过反式三氯单氧代-双(三苯基膦)铼(V)与HSN(R-)SH和RSH的混合物在碱性甲醇溶液中的配体交换合成。通过柱色谱法纯化络合物，并通过元素分析、质谱和红外光谱进行表征，并通过 1 H NMR 光谱对选定的化合物进行表征。这些配合物的结构已通过 X 射线衍射分析确定，并揭示了配位几何形状从方锥体到三角双锥体的变化，具体取决于螯合 (SN(R−)S) 部分。发现烷基(R-2)与氧铼基团排列成-syn-。