(1E,6E)-4-[(4-hydroxyphenyl)methylidene]-1,7-bis(4-hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5-disemicarbazone | 1384422-86-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (1E,6E)-4-[(4-hydroxyphenyl)methylidene]-1,7-bis(4-hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5-disemicarbazone
• CAS: 1384422-86-9
• 化学式: C₃₀H₃₀N₆O₇
• 分子量: 586.604
• InChiKey: SZYRHSPXCQOZON-SBGMBJCMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.68
• 重原子数：
  43.0
• 可旋转键数：
  11.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  214.11
• 氢给体数：
  7.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  (1E,6E)-4-[(4-hydroxyphenyl)methylidene]-1,7-bis(4-hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5-disemicarbazone 、 ruthenium(III) chloride trihydrate 以 甲醇 为溶剂， 反应 3.0h， 生成 N'-[(E)-[(1E,5E,6E)-5-[(Z)-[amino(hydroxy)methylidene]hydrazinylidene]-1,7-bis(4-hydroxy-3-methoxyphenyl)-4-[(4-hydroxyphenyl)methylidene]hepta-1,6-dien-3-ylidene]amino]carbamimidic acid;ruthenium(3+);trichloride
  参考文献：
  名称：

  Synthesis, DNA binding, hemolytic, and anti-cancer assays of curcumin I-based ligands and their ruthenium(III) complexes

  摘要：

  Knoevenagel condensates of curcumin I were synthesized with p-hydroxybenzaldehyde and 4-hydroxy-3,5-dimethoxy benzaldehyde and allowed to react with semicarbazide to form the corresponding curcumin I-based ligands. The ligands were complexed with ruthenium(III) metal ions. These complexes (C-1 and C-2) were purified by chromatography and characterized as octahedral geometries by analytical techniques. The binding affinities of these compounds for calf thymus DNA were determined. DNA binding constants (K (b) ) for the two complexes were 1.46 x 10(4) and 3.54 x 10(4) M-1, respectively. Similarly, the binding constants (K (sv)) for C-1 and C-2 were 9.40 x 10(3) and 9.30 x 10(3) M-1, respectively. Hemolytic assays of the compounds showed less toxicity than the standard anti-cancer drug letrazole. The compounds showed good activity against the cervical cancer cell line (HeLa) and moderate activity against liver hepatocellular carcinoma (HepG2), breast cancer (MDA-MB-231) and human colon adenocarcinoma (HT-29) cells lines. These compounds showed potential for treatment of cervical cancer in the future.

  DOI：

  10.1007/s00044-012-0133-8
• 作为产物：
  描述：

  姜黄素 在 哌啶 作用下， 以 甲醇 、 氯仿 、 水 为溶剂， 反应 72.0h， 生成 (1E,6E)-4-[(4-hydroxyphenyl)methylidene]-1,7-bis(4-hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5-disemicarbazone
  参考文献：
  名称：

  Synthesis, DNA binding, hemolytic, and anti-cancer assays of curcumin I-based ligands and their ruthenium(III) complexes

  摘要：

  Knoevenagel condensates of curcumin I were synthesized with p-hydroxybenzaldehyde and 4-hydroxy-3,5-dimethoxy benzaldehyde and allowed to react with semicarbazide to form the corresponding curcumin I-based ligands. The ligands were complexed with ruthenium(III) metal ions. These complexes (C-1 and C-2) were purified by chromatography and characterized as octahedral geometries by analytical techniques. The binding affinities of these compounds for calf thymus DNA were determined. DNA binding constants (K (b) ) for the two complexes were 1.46 x 10(4) and 3.54 x 10(4) M-1, respectively. Similarly, the binding constants (K (sv)) for C-1 and C-2 were 9.40 x 10(3) and 9.30 x 10(3) M-1, respectively. Hemolytic assays of the compounds showed less toxicity than the standard anti-cancer drug letrazole. The compounds showed good activity against the cervical cancer cell line (HeLa) and moderate activity against liver hepatocellular carcinoma (HepG2), breast cancer (MDA-MB-231) and human colon adenocarcinoma (HT-29) cells lines. These compounds showed potential for treatment of cervical cancer in the future.

  DOI：

  10.1007/s00044-012-0133-8