2-(2-hydroxy-5-methoxycarbonyl-phenyl)-4,5-dihydrothiazole-4-carboxylic acid | 1144112-92-4

• 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: 2-(2-hydroxy-5-methoxycarbonyl-phenyl)-4,5-dihydrothiazole-4-carboxylic acid
• 英文别名: 2-(2-Hydroxy-5-methoxycarbonylphenyl)-4,5-dihydro-1,3-thiazole-4-carboxylic acid
• CAS: 1144112-92-4
• 化学式: C₁₂H₁₁NO₅S
• 分子量: 281.289
• InChiKey: HAAZLRFNMUESLY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  122
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  L-半胱氨酸 、 3-cyano-4-hydroxymethylbenzoic acid methyl ester 以 甲醇 、 水 为溶剂， 反应 16.0h， 生成 2-(2-hydroxy-5-methoxycarbonyl-phenyl)-4,5-dihydrothiazole-4-carboxylic 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

文献信息

• [EN] NOVEL COMPOUNDS, PREPARATION AND USES THEREOF<br/>[FR] NOUVEAUX COMPOSES, PRÉPARATION ET UTILISATIONS
  申请人：UNIV PASTEUR

  公开号：WO2009053628A2

  公开（公告）日：2009-04-30

  La présente invention concerne de nouveaux composés, les compositions pharmaceutiques les comprenant ainsi que leurs applications thérapeutiques dans les domaines de la santé humaine et animale. La présente invention a également trait à un procédé de préparation de ces composés.