(E)-7-(2,5-dimethoxybenzylidene)-3-(2,5-dimethoxyphenyl)-3,3a,4,5,6,7-hexahydro-2H-indazole | 1383969-68-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: (E)-7-(2,5-dimethoxybenzylidene)-3-(2,5-dimethoxyphenyl)-3,3a,4,5,6,7-hexahydro-2H-indazole
• 英文别名: (e)-7-(2,5-Dimethoxybenzylidene)-3-(2,5-dimethoxyphenyl)-3,3a,4,5,6,7-hexahydro-2h-indazole；(7E)-3-(2,5-dimethoxyphenyl)-7-[(2,5-dimethoxyphenyl)methylidene]-2,3,3a,4,5,6-hexahydroindazole
• CAS: 1383969-68-3
• 化学式: C₂₄H₂₈N₂O₄
• 分子量: 408.497
• InChiKey: LBYLUJZFUBILFH-NTCAYCPXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  61.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (2E,6E)-2,6-bis(2,5-dimethoxybenzylidene)cyclohexanone 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 21.0h， 以78%的产率得到(E)-7-(2,5-dimethoxybenzylidene)-3-(2,5-dimethoxyphenyl)-3,3a,4,5,6,7-hexahydro-2H-indazole
  参考文献：
  名称：

  Synthesis and biological evaluation of new curcumin derivatives as antioxidant and antitumor agents

  摘要：

  Twenty-four new compounds were prepared, taking curcumin as a lead, in order to explore their antioxidant and antitumor properties. The capacities of these derivatives to scavenge the 2,2'-azinobis(3-ethylbenzothiazoline-6-sulfonic acid) radical cation (ABTS(.+)), and to protect human red blood cells (RBCs) from oxidative haemolysis were investigated. In addition, the percentage viability of different cell lines (Hep G2, WI38, VERO and MCF-7) was tested. The result of the antitumor testing was generally in accordance with those of the antioxidant assays. Compounds which bear o-methoxy substitution to the 4-hydroxy function in the phenyl ring (7g, 5g and 3g) exhibited significantly higher ABTS(.+)-scavenging, antihaemolysis, and antitumor activities than other derivatives. In addition, molecular modelling studies were carried out for biologically active and inactive compounds, to study the structure-activity relationship, with the aim to elucidate which portions of the molecules are critical for the antioxidant and antitumor activity.

  DOI：

  10.1007/s00044-012-0116-9

文献信息

• Synthesis and biological evaluation of new curcumin derivatives as antioxidant and antitumor agents
  作者：Said M. Bayomi、Hassan A. El-Kashef、Mahmoud B. El-Ashmawy、Magda N. A. Nasr、Magda A. El-Sherbeny、Farid A. Badria、Laila A. Abou-zeid、Mariam A. Ghaly、Naglaa I. Abdel-Aziz

  DOI：10.1007/s00044-012-0116-9

  日期：2013.3

  Twenty-four new compounds were prepared, taking curcumin as a lead, in order to explore their antioxidant and antitumor properties. The capacities of these derivatives to scavenge the 2,2'-azinobis(3-ethylbenzothiazoline-6-sulfonic acid) radical cation (ABTS(.+)), and to protect human red blood cells (RBCs) from oxidative haemolysis were investigated. In addition, the percentage viability of different cell lines (Hep G2, WI38, VERO and MCF-7) was tested. The result of the antitumor testing was generally in accordance with those of the antioxidant assays. Compounds which bear o-methoxy substitution to the 4-hydroxy function in the phenyl ring (7g, 5g and 3g) exhibited significantly higher ABTS(.+)-scavenging, antihaemolysis, and antitumor activities than other derivatives. In addition, molecular modelling studies were carried out for biologically active and inactive compounds, to study the structure-activity relationship, with the aim to elucidate which portions of the molecules are critical for the antioxidant and antitumor activity.