dimethyl 3,3'-((5,8-dioxa-2,11-diazadodecanedioyl)bis(4,5-dihydrothiazole-4,2-diyl))bis(4-hydroxybenzoate) | 1144112-93-5

• 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: dimethyl 3,3'-((5,8-dioxa-2,11-diazadodecanedioyl)bis(4,5-dihydrothiazole-4,2-diyl))bis(4-hydroxybenzoate)
• CAS: 1144112-93-5
• 化学式: C₃₀H₃₄N₄O₁₀S₂
• 分子量: 674.753
• InChiKey: ODEHZMZKMSVSJO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.36
• 重原子数：
  46.0
• 可旋转键数：
  15.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  194.44
• 氢给体数：
  4.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  dimethyl 3,3'-((5,8-dioxa-2,11-diazadodecanedioyl)bis(4,5-dihydrothiazole-4,2-diyl))bis(4-hydroxybenzoate) 在 三氯溴甲烷 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 14.0h， 以444 mg的产率得到3,3'-[(1,12-dioxo-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
• 作为产物：
  描述：

  1,8-二氨基-3,6-二氧杂辛烷 、 2-(2-hydroxy-5-methoxycarbonyl-phenyl)-4,5-dihydrothiazole-4-carboxylic acid 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 生成 dimethyl 3,3'-((5,8-dioxa-2,11-diazadodecanedioyl)bis(4,5-dihydrothiazole-4,2-diyl))bis(4-hydroxybenzoate)
  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