(±)-carbonic acid 2-(3-benzyl-2,4-dioxothiazolidin-(5Z)-ylidenemethyl)-2,5,7,8-tetramethylchroman-6-yl-tert-butyl ester | 1621471-10-0

• 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: (±)-carbonic acid 2-(3-benzyl-2,4-dioxothiazolidin-(5Z)-ylidenemethyl)-2,5,7,8-tetramethylchroman-6-yl-tert-butyl ester
• 英文别名: [2-[(Z)-(3-benzyl-2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl]-2,5,7,8-tetramethyl-3,4-dihydrochromen-6-yl] tert-butyl carbonate
• CAS: 1621471-10-0
• 化学式: C₂₉H₃₃NO₆S
• 分子量: 523.65
• InChiKey: CYIYCLYGBXIDNP-JCMHNJIXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  37
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  107
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (±)-carbonic acid 2-(3-benzyl-2,4-dioxothiazolidin-(5Z)-ylidenemethyl)-2,5,7,8-tetramethylchroman-6-yl-tert-butyl ester 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以88%的产率得到(±)-3-benzyl-(5Z)-(6-hydroxy-2,5,7,8-tetramethylchroman-2-ylmethylene)thiazolidine-2,4-dione
  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：

  ethyl 6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-chromene-2-carboxylate 在 哌啶 、 4-二甲氨基吡啶 、 二异丁基氢化铝 、 potassium carbonate 、 苯甲酸 作用下， 以 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 3.0h， 生成 (±)-carbonic acid 2-(3-benzyl-2,4-dioxothiazolidin-(5Z)-ylidenemethyl)-2,5,7,8-tetramethylchroman-6-yl-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

文献信息

• Optimization of troglitazone derivatives as potent anti-proliferative agents: Towards more active and less toxic compounds
  作者：Andrea Bordessa、Christelle Colin-Cassin、Isabelle Grillier-Vuissoz、Sandra Kuntz、Sabine Mazerbourg、Gauthier Husson、Myriam Vo、Stéphane Flament、Hélène Martin、Yves Chapleur、Michel Boisbrun

  DOI：10.1016/j.ejmech.2014.06.015

  日期：2014.8

  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.