2-(3',4'-dimethoxybenzylidene)-4-methoxy-7-piperidinocarbonyloxy-2,3-dihydro-benzo[b]thiophen-3-one | 865851-38-3

• 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-(3',4'-dimethoxybenzylidene)-4-methoxy-7-piperidinocarbonyloxy-2,3-dihydro-benzo[b]thiophen-3-one
• 英文别名: [(2Z)-2-[(3,4-dimethoxyphenyl)methylidene]-4-methoxy-3-oxo-1-benzothiophen-7-yl] piperidine-1-carboxylate
• CAS: 865851-38-3
• 化学式: C₂₄H₂₅NO₆S
• 分子量: 455.532
• InChiKey: URBCDTFHXOKQMS-ZHZULCJRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  99.6
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-(3',4'-dimethoxybenzylidene)-4-methoxy-7-piperidinocarbonyloxy-2,3-dihydro-benzo[b]thiophen-3-one 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以77%的产率得到2-[1-(3,4-Dimethoxy-phenyl)-meth-(Z)-ylidene]-7-hydroxy-4-methoxy-benzo[b]thiophen-3-one
  参考文献：
  名称：

  Synthesis and Cytostatic Activity of 4,7-Dihydroxythioaurone Derivatives. Effect of B Ring Substitution on the Activity

  摘要：

  迄今为止，人们尚未测试过硫代金 属化合物的生物活性，因此该类化合物是完全未开发的具有药理学意义的新分子来源。我们报告了在环 A 中含有对氢醌系统的硫代金酸盐衍生物的合成和细胞毒性活性评估。研究发现它们的活性与取代模式密切相关，因此最终可以通过进一步的结构修饰来调整分子的活性和药代动力学参数。

  DOI：

  10.1248/cpb.54.350
• 作为产物：
  描述：

  4-acetyl-5-hydroxybenzo[1,3]oxathiol-2-one 在 potassium carbonate 、 二甲基亚砜 作用下， 以 丙酮 为溶剂， 反应 3.0h， 生成 2-(3',4'-dimethoxybenzylidene)-4-methoxy-7-piperidinocarbonyloxy-2,3-dihydro-benzo[b]thiophen-3-one
  参考文献：
  名称：

  New domino reaction. One pot synthesis of 4,7-dihydroxythioaurone derivatives from benzaldehydes and 4-acetyl-2-oxo-benz[1,3]oxathiole

  摘要：

  A convenient synthesis of 4,7-dihydroxythioaurone derivatives by a one pot reaction of benzaldehydes with 4-acetyl-2-oxobenz[1,3]oxathioles and piperidine acetate in DMSO is described. The structures of the compounds, including double bond geometry were proved unequivocally by NMR methods. The thioaurone ring system seems to be formed by three consecutive reactions: opening of the oxathiolone ring with piperidine, oxidation of the formed mercapto group with DMSO or/and air to disulfide, and condensation with aldehyde. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.06.107

文献信息

• New domino reaction. One pot synthesis of 4,7-dihydroxythioaurone derivatives from benzaldehydes and 4-acetyl-2-oxo-benz[1,3]oxathiole
  作者：Marek T. Konieczny、Wojciech Konieczny、Stefan Wolniewicz、Konstanty Wierzba、Yoshimitsu Suda、Paweł Sowiński

  DOI：10.1016/j.tet.2005.06.107

  日期：2005.9

  A convenient synthesis of 4,7-dihydroxythioaurone derivatives by a one pot reaction of benzaldehydes with 4-acetyl-2-oxobenz[1,3]oxathioles and piperidine acetate in DMSO is described. The structures of the compounds, including double bond geometry were proved unequivocally by NMR methods. The thioaurone ring system seems to be formed by three consecutive reactions: opening of the oxathiolone ring with piperidine, oxidation of the formed mercapto group with DMSO or/and air to disulfide, and condensation with aldehyde. (c) 2005 Elsevier Ltd. All rights reserved.
• Synthesis and Cytostatic Activity of 4,7-Dihydroxythioaurone Derivatives. Effect of B Ring Substitution on the Activity
  作者：Marek Tadeusz Konieczny、Wojciech Konieczny、Soko Okabe、Hiroaki Tsujimoto、Yoshimitsu Suda、Konstanty Wierzba

  DOI：10.1248/cpb.54.350

  日期：——

  Biological activity of thioaurones was not tested so far and the group constitute completely unexplored source of new molecules of pharmacological interest. We report synthesis and evaluation of cytotoxic activity of thioaurone derivatives bearing p-hydroquinone system in ring A. Their activity was found to depend strongly on substitution pattern, so eventually both the activity and pharmacokinetic parameters of the molecules could be tailored by further structural modifications.

  迄今为止，人们尚未测试过硫代金 属化合物的生物活性，因此该类化合物是完全未开发的具有药理学意义的新分子来源。我们报告了在环 A 中含有对氢醌系统的硫代金酸盐衍生物的合成和细胞毒性活性评估。研究发现它们的活性与取代模式密切相关，因此最终可以通过进一步的结构修饰来调整分子的活性和药代动力学参数。