(±)-(6-{2,5,7,8-tetramethyl-2-[4-(3-methyl-2,4-dioxothiazolidin-(5Z)-ylidenemethyl)phenoxymethyl]chroman-6-yl}hexyl)carbamic acid tert-butyl ester | 1621470-75-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (±)-(6-{2,5,7,8-tetramethyl-2-[4-(3-methyl-2,4-dioxothiazolidin-(5Z)-ylidenemethyl)phenoxymethyl]chroman-6-yl}hexyl)carbamic acid tert-butyl ester
• CAS: 1621470-75-4
• 化学式: C₃₆H₄₈N₂O₆S
• 分子量: 636.853
• InChiKey: KIEMICOFAUISMW-OFWBYEQRSA-N

物化性质

• 熔点：
  112-114 °C
• 密度：
  1.161±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.07
• 重原子数：
  45.0
• 可旋转键数：
  11.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  94.17
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (±)-(6-{2,5,7,8-tetramethyl-2-[4-(3-methyl-2,4-dioxothiazolidin-(5Z)-ylidenemethyl)phenoxymethyl]chroman-6-yl}hexyl)carbamic acid tert-butyl ester 、 三氟乙酸 以 二氯甲烷 为溶剂， 反应 3.0h， 以54%的产率得到(±)-(5Z)-{4-[6-(6-aminohexyl)-2,5,7,8-tetramethylchroman-2-ylmethoxy]benzylidene}-3-methylthiazolidine-2,4-dione trifluoroacetic acid salt
  参考文献：
  名称：

  Optimization of troglitazone derivatives as potent anti-proliferative agents: Towards more active and less toxic compounds

  摘要：

  Δ2-Troglitazone derivatives were shown to exhibit anti-proliferative activity in a PPARγ-independent manner. We prepared various compounds in order to increase their potency and decrease their toxicity towards non-malignant primary cultured hepatocytes. Many compounds induced viabilities less than 20% at 10 μM on various cancer cell lines. Furthermore, five of them showed hepatocyte viability of 80% or more at 200 μM. In addition, compounds 17 and 18 exhibited promising maximum tolerated doses on a murine model, enabling future investigations.

  DOI：

  10.1016/j.ejmech.2014.06.015
• 作为产物：
  描述：

  6-溴己酰氯 在 哌啶 、 吡啶 、 aluminum (III) chloride 、 lithium aluminium tetrahydride 、 sodium azide 、 palladium on activated charcoal 、 氢气 、 potassium carbonate 、 苯甲酸 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 59.33h， 生成 (±)-(6-{2,5,7,8-tetramethyl-2-[4-(3-methyl-2,4-dioxothiazolidin-(5Z)-ylidenemethyl)phenoxymethyl]chroman-6-yl}hexyl)carbamic acid tert-butyl ester
  参考文献：
  名称：

  Optimization of troglitazone derivatives as potent anti-proliferative agents: Towards more active and less toxic compounds

  摘要：

  Δ2-Troglitazone derivatives were shown to exhibit anti-proliferative activity in a PPARγ-independent manner. We prepared various compounds in order to increase their potency and decrease their toxicity towards non-malignant primary cultured hepatocytes. Many compounds induced viabilities less than 20% at 10 μM on various cancer cell lines. Furthermore, five of them showed hepatocyte viability of 80% or more at 200 μM. In addition, compounds 17 and 18 exhibited promising maximum tolerated doses on a murine model, enabling future investigations.

  DOI：

  10.1016/j.ejmech.2014.06.015