3,5-bis(4-hydroxy-3-methoxystyryl)-1H-pyrazole-1-yl-(4-pyridyl)methanone

• 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: 3,5-bis(4-hydroxy-3-methoxystyryl)-1H-pyrazole-1-yl-(4-pyridyl)methanone
• 英文别名: (3,5-bis(4-hydroxy-3-methoxystyryl)-1H-pyrazol-1-yl)(pyridine-4-yl)methanone；[3,5-bis[(E)-2-(4-hydroxy-3-methoxy-phenyl)vinyl]pyrazol-1-yl]-(4-pyridyl)methanone；[3,5-bis[(E)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]pyrazol-1-yl]-pyridin-4-ylmethanone
• 化学式: C₂₇H₂₃N₃O₅
• 分子量: 469.497
• InChiKey: UFDSAXFMNUUEEN-FCXRPNKRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  35
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  107
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  异烟酸乙酯 在 溶剂黄146 、 肼 作用下， 以 乙醇 为溶剂， 反应 24.0h， 生成 3,5-bis(4-hydroxy-3-methoxystyryl)-1H-pyrazole-1-yl-(4-pyridyl)methanone
  参考文献：
  名称：

  Synthesis, antiproliferative activity, and molecular docking studies of curcumin analogues bearing pyrazole ring

  摘要：

  Several curcumin analogues bearing pyrazole were synthesized and characterized by IR, NMR, and mass spectral data. There were four tested compounds among 11 synthesized compounds, which were evaluated for antiproliferative activity and showed significant activity in both one-dose and five-dose assays. The antiproliferative effects were tested on a panel of 60 cell lines, according to the National Cancer Institute screening protocol. The most active compounds among the series were 3,5-bis(4-hydroxy-3-methylstyryl)-1H-pyrazole-1-carboxamide (3k) which showed mean percent growth inhibition of 116.09 in one-dose assay at 10 A mu M, and GI(50) values were ranging between 0.0912 and 2.36 A mu M in five-dose assay. The best results were recorded on the leukaemia cell lines with value ranging from 0.0912 to 0.365 A mu M. All the tested compounds showed broad-spectrum antiproliferative activity over different cancer cell lines. When compared with the standard drug paclitaxel, the compound 3k showed superior activity on nearly 42 cell lines. The molecular docking study was performed to explore the binding interaction of these curcumin analogues with the active site of EGFR tyrosine kinase (EGFR-TK). The hydroxyl group of both phenyl rings was important for the rein-geminated hydrogen bonding by either side chain or backbone with the active site of EGFR-TK.Four curcumin analogues were evaluated for their antiproliferative activity and showed promising results. The molecular docking studies showed that all the compounds (3a-k) were well accommodated in the EGFR tyrosine kinase.[GRAPHICS].

  DOI：

  10.1007/s00044-015-1457-y

文献信息

• Structure activity relationship, cytotoxicity and evaluation of antioxidant activity of curcumin derivatives
  作者：Pramod K. Sahu、Praveen K. Sahu、Puran L. Sahu、Dau D. Agarwal

  DOI：10.1016/j.bmcl.2015.12.013

  日期：2016.2

  compound 3c, (IC50 value 6.25 μM) has shown better cytotoxicity effect against three cell lines. According to results of SAR study, it was found that 4H-pyrimido[2,1-b]benzothiazole derivatives (2e and 2f), pyrazoles (3a, 3b, 3c and 3d) benzylidenes (4d) exhibited better antioxidant activity than curcumin. A correlation of structure and activities relationship of these compounds with respect to drug

  设计了一系列姜黄素衍生物/类似物，并描述了其合成的有效方法。筛选所有合成的化合物的细胞毒性并评估其抗氧化活性。已经通过MTT测定法评估了针对三种细胞系Hep-G2，HCT-116和QG-56的细胞毒性作用。结构活性关系表明，特别是化合物3c（IC50值为6.25μM）对三种细胞系表现出更好的细胞毒性作用。根据SAR研究的结果，发现4H-嘧啶并[2,1-b]苯并噻唑衍生物（2e和2f），吡唑（3a，3b，3c和3d）亚苄基（4d）具有比姜黄素更好的抗氧化活性。
• Synthesis, antiproliferative activity, and molecular docking studies of curcumin analogues bearing pyrazole ring
  作者：Mohamed Jawed Ahsan、Kavita Choudhary、Surender Singh Jadav、Sabina Yasmin、Md. Yousuf Ansari、Reddymasu Sreenivasulu

  DOI：10.1007/s00044-015-1457-y

  日期：2015.12

  Several curcumin analogues bearing pyrazole were synthesized and characterized by IR, NMR, and mass spectral data. There were four tested compounds among 11 synthesized compounds, which were evaluated for antiproliferative activity and showed significant activity in both one-dose and five-dose assays. The antiproliferative effects were tested on a panel of 60 cell lines, according to the National Cancer Institute screening protocol. The most active compounds among the series were 3,5-bis(4-hydroxy-3-methylstyryl)-1H-pyrazole-1-carboxamide (3k) which showed mean percent growth inhibition of 116.09 in one-dose assay at 10 A mu M, and GI(50) values were ranging between 0.0912 and 2.36 A mu M in five-dose assay. The best results were recorded on the leukaemia cell lines with value ranging from 0.0912 to 0.365 A mu M. All the tested compounds showed broad-spectrum antiproliferative activity over different cancer cell lines. When compared with the standard drug paclitaxel, the compound 3k showed superior activity on nearly 42 cell lines. The molecular docking study was performed to explore the binding interaction of these curcumin analogues with the active site of EGFR tyrosine kinase (EGFR-TK). The hydroxyl group of both phenyl rings was important for the rein-geminated hydrogen bonding by either side chain or backbone with the active site of EGFR-TK.Four curcumin analogues were evaluated for their antiproliferative activity and showed promising results. The molecular docking studies showed that all the compounds (3a-k) were well accommodated in the EGFR tyrosine kinase.[GRAPHICS].