3,3'-[(1,12-dithioxo-5,8-dioxa-2,11-diazadodecane-1,12-diyl)bis(4,2-thiazolediyl)]bis-[4-hydroxybenzoic acid] dimethyl ester | 1144112-95-7

• 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: 3,3'-[(1,12-dithioxo-5,8-dioxa-2,11-diazadodecane-1,12-diyl)bis(4,2-thiazolediyl)]bis-[4-hydroxybenzoic acid] dimethyl ester
• 英文别名: Methyl 4-hydroxy-3-[4-[2-[2-[2-[[2-(2-hydroxy-5-methoxycarbonylphenyl)-1,3-thiazole-4-carbothioyl]amino]ethoxy]ethoxy]ethylcarbamothioyl]-1,3-thiazol-2-yl]benzoate；methyl 4-hydroxy-3-[4-[2-[2-[2-[[2-(2-hydroxy-5-methoxycarbonylphenyl)-1,3-thiazole-4-carbothioyl]amino]ethoxy]ethoxy]ethylcarbamothioyl]-1,3-thiazol-2-yl]benzoate
• CAS: 1144112-95-7
• 化学式: C₃₀H₃₀N₄O₈S₄
• 分子量: 702.854
• InChiKey: VNTRYRPILPEWFC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  46
• 可旋转键数：
  17
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  282
• 氢给体数：
  4
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  3,3'-[(1,12-dithioxo-5,8-dioxa-2,11-diazadodecane-1,12-diyl)bis(4,2-thiazolediyl)]bis-[4-hydroxybenzoic acid] dimethyl ester 在 水 、 potassium hydroxide 、 盐酸 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 2.0h， 以59%的产率得到3,3'-[(1,12-dithioxo-5,8-dioxa-2,11-diazadodecane-1,12-diyl)bis(4,2-thiazolediyl)]bis[4-hydroxybenzoic acid]
  参考文献：
  名称：

  Synthesis and biological properties of iron chelators based on a bis-2-(2-hydroxy-phenyl)-thiazole-4-carboxamide or -thiocarboxamide (BHPTC) scaffold

  摘要：

  Bis-2-(2-hydroxy-phenyl)-thiazole-4-carboxamides and -thiocarboxamides (BHPTCs) form a family of gemini hexacoordinated bis-tridentate chelating scaffolds. Four molecules were synthesized and shown to chelate iron(III) efficiently with a 1:1 stoichiometry. A dithioamide BHPTC displayed promising anti-proliferative activity in several cancerous cell lines, making this molecule an interesting lead compound for the design of new iron-chelating anticancer drugs. Conversely, diamide BHPTCs had significant cytoprotective activity against iron overload in HepaRG cells in vitro, and were as efficient as and less toxic than deferoxamine B (DFO). (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.11.057
• 作为产物：
  描述：

  3,3'-[(1,12-dioxo-5,8-dioxa-2,11-diazadodecane-1,12-diyl)-bis(4,2-thiazolediyl)]bis-[4-hydroxybenzoic acid] dimethyl ester 在 劳森试剂 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以96%的产率得到3,3'-[(1,12-dithioxo-5,8-dioxa-2,11-diazadodecane-1,12-diyl)bis(4,2-thiazolediyl)]bis-[4-hydroxybenzoic acid] dimethyl ester
  参考文献：
  名称：

  Synthesis and biological properties of iron chelators based on a bis-2-(2-hydroxy-phenyl)-thiazole-4-carboxamide or -thiocarboxamide (BHPTC) scaffold

  摘要：

  Bis-2-(2-hydroxy-phenyl)-thiazole-4-carboxamides and -thiocarboxamides (BHPTCs) form a family of gemini hexacoordinated bis-tridentate chelating scaffolds. Four molecules were synthesized and shown to chelate iron(III) efficiently with a 1:1 stoichiometry. A dithioamide BHPTC displayed promising anti-proliferative activity in several cancerous cell lines, making this molecule an interesting lead compound for the design of new iron-chelating anticancer drugs. Conversely, diamide BHPTCs had significant cytoprotective activity against iron overload in HepaRG cells in vitro, and were as efficient as and less toxic than deferoxamine B (DFO). (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.11.057

文献信息

• Synthesis and biological properties of iron chelators based on a bis-2-(2-hydroxy-phenyl)-thiazole-4-carboxamide or -thiocarboxamide (BHPTC) scaffold
  作者：David Rodriguez-Lucena、François Gaboriau、Freddy Rivault、Isabelle J. Schalk、Gérard Lescoat、Gaëtan L.A. Mislin

  DOI：10.1016/j.bmc.2009.11.057

  日期：2010.1

  Bis-2-(2-hydroxy-phenyl)-thiazole-4-carboxamides and -thiocarboxamides (BHPTCs) form a family of gemini hexacoordinated bis-tridentate chelating scaffolds. Four molecules were synthesized and shown to chelate iron(III) efficiently with a 1:1 stoichiometry. A dithioamide BHPTC displayed promising anti-proliferative activity in several cancerous cell lines, making this molecule an interesting lead compound for the design of new iron-chelating anticancer drugs. Conversely, diamide BHPTCs had significant cytoprotective activity against iron overload in HepaRG cells in vitro, and were as efficient as and less toxic than deferoxamine B (DFO). (C) 2009 Elsevier Ltd. All rights reserved.