5-methoxybenzothiophene-4-carboxaldehyde | 1268272-51-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: 5-methoxybenzothiophene-4-carboxaldehyde
• 英文别名: 5-Methoxy-1-benzothiophene-4-carbaldehyde
• CAS: 1268272-51-0
• 化学式: C₁₀H₈O₂S
• 分子量: 192.238
• InChiKey: CDOVGJQVYPUWKE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  54.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-methoxybenzothiophene-4-carboxaldehyde 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 以84 %的产率得到5-hydroxy-benzo[b]thiophene-4-carbaldehyde
  参考文献：
  名称：

  US2023/128569

  摘要：

  公开号：
• 作为产物：
  描述：

  4-甲氧基苯硫酚 在 磷酸 、 sodium methylate 、 四氯化锡 作用下， 以 甲醇 、 5,5-dimethyl-1,3-cyclohexadiene 、 二氯甲烷 为溶剂， 生成 5-methoxybenzothiophene-4-carboxaldehyde
  参考文献：
  名称：

  Antitumor Agents. 284. New Desmosdumotin B Analogues with Bicyclic B-Ring as Cytotoxic and Antitubulin Agents

  摘要：

  We previously reported that the biological activity of analogues of desmosdumotin B (1) was dramatically changed depending on the B-ring system. A naphthalene B-ring analogue 3 exerted potent in vitro activity against a diverse panel of human tumor cell lines with GI(50) values of 0.8-2.1 mu M. In contrast, 1 analogues with a phenyl B-ring showed unique selective activity against P-glycoprotein (P-gp) over-expressing multidrug resistant cell line. We have now prepared and evaluated, 1 analogues with bicyclic or tricyclic aromatic B-ring systems as in vitro inhibitors of human cancer cell line proliferation. Among all synthesized derivatives, 21 with a benzo[b]thiophenyl B-ring was highly active, with GI(50) values of 0.06-0.16 mu M, and this activity was not influenced by overexpression of P-gp. Furthermore, 21 inhibited tubulin assembly in vitro with an IC(50) value of 2.0 mu M and colchicine binding by 7896 as well as cellular microtubule polymerization and spindle formation.

  DOI：

  10.1021/jm1011947

文献信息

• NEW COMPOUND AND USE THEREOF
  申请人：Daicel Corporation

  公开号：EP4108657A1

  公开（公告）日：2022-12-28

  Provided is a compound that is excellent in chemical stability, has a high solubility in a solvent, and exhibits an excellent carrier mobility. A compound represented by Formula (1): where in Formula (1), X1, X2, X3, and R1 to R10 are as defined in the specification.

  本发明提供了一种化学稳定性极佳、在溶剂中溶解度高、载体流动性极佳的化合物。 由式（1）表示的化合物： 式（1）中，X1、X2、X3 和 R1 至 R10 如说明书中所定义。