7-(4-nitrobenzylidene)-3-(4-nitrophenyl)-3,3a,4,5,6,7-hexahydro-2H-indazole | 99160-05-1

• 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: 7-(4-nitrobenzylidene)-3-(4-nitrophenyl)-3,3a,4,5,6,7-hexahydro-2H-indazole
• 英文别名: 3-(4-nitrophenyl)-7-[(4-nitrophenyl)methylidene]-2,3,3a,4,5,6-hexahydroindazole
• CAS: 99160-05-1
• 化学式: C₂₀H₁₈N₄O₄
• 分子量: 378.387
• InChiKey: SJMNREBVDHZEOD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  28
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  116
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 7-(4-nitrobenzylidene)-3-(4-nitrophenyl)-3,3a,4,5,6,7-hexahydro-2H-indazole 在 4-二甲氨基吡啶 作用下， 反应 3.0h， 以92%的产率得到1-(7-(4-nitrobenzylidene)-3-(4-nitrophenyl)-3,3a,4,5,6,7-hexahydro-2H-indazol-2-yl)ethanone
  参考文献：
  名称：

  Synthesis and evaluation of DPPH and anti-inflammatory activities of 2,6-bisbenzylidenecyclohexanone and pyrazoline derivatives

  摘要：

  A series of thirty three 2,6-bisbenzylidenecyclohexanone and pyrazoline derivatives were synthesized and evaluated for inhibitory activities on IFN-gamma/LPS-activated RAW 264.7 cells and DPPH radical scavenging activity. Compounds 8, 9, and 11a demonstrated significant NO inhibitory activity as compared to L-NAME and curcumin with IC50 values of 6.68 +/- A 0.16, 6.09 +/- A 0.46, and 6.84 +/- A 0.12 mu M, respectively. Apparently the suppression upon NO secretion was not due to cell death since the active compounds did not reduce the cell viability in close proximity to the IC50 of NO inhibition. Overall, incorporation of pyrazoline ring as part of the linker chain improved cell viability compared to the 2,6-bisbenzylidenecyclohexanone derivatives. Meanwhile, compound 11 (IC50 = 13.27 +/- A 1.78 mu M) bearing ortho hydroxyls on the aromatic rings recorded the highest radical scavenging activity as compared with quercetin (IC50 = 21.46 +/- A 0.85 mu M).

  DOI：

  10.1007/s00044-010-9521-0
• 作为产物：
  描述：

  2,6-di(p-nitrobenzylidene)cyclohexanone 在 一水合肼 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以62%的产率得到7-(4-nitrobenzylidene)-3-(4-nitrophenyl)-3,3a,4,5,6,7-hexahydro-2H-indazole
  参考文献：
  名称：

  Synthesis and evaluation of DPPH and anti-inflammatory activities of 2,6-bisbenzylidenecyclohexanone and pyrazoline derivatives

  摘要：

  A series of thirty three 2,6-bisbenzylidenecyclohexanone and pyrazoline derivatives were synthesized and evaluated for inhibitory activities on IFN-gamma/LPS-activated RAW 264.7 cells and DPPH radical scavenging activity. Compounds 8, 9, and 11a demonstrated significant NO inhibitory activity as compared to L-NAME and curcumin with IC50 values of 6.68 +/- A 0.16, 6.09 +/- A 0.46, and 6.84 +/- A 0.12 mu M, respectively. Apparently the suppression upon NO secretion was not due to cell death since the active compounds did not reduce the cell viability in close proximity to the IC50 of NO inhibition. Overall, incorporation of pyrazoline ring as part of the linker chain improved cell viability compared to the 2,6-bisbenzylidenecyclohexanone derivatives. Meanwhile, compound 11 (IC50 = 13.27 +/- A 1.78 mu M) bearing ortho hydroxyls on the aromatic rings recorded the highest radical scavenging activity as compared with quercetin (IC50 = 21.46 +/- A 0.85 mu M).

  DOI：

  10.1007/s00044-010-9521-0

文献信息

• Synthesis and evaluation of DPPH and anti-inflammatory activities of 2,6-bisbenzylidenecyclohexanone and pyrazoline derivatives
  作者：Kok Wai Lam、Chau Ling Tham、Choi Yi Liew、Ahmad Syahida、Mohd. Basyaruddin Abdul Rahman、Daud A. Israf、Nordin H. Lajis

  DOI：10.1007/s00044-010-9521-0

  日期：2012.3

  A series of thirty three 2,6-bisbenzylidenecyclohexanone and pyrazoline derivatives were synthesized and evaluated for inhibitory activities on IFN-gamma/LPS-activated RAW 264.7 cells and DPPH radical scavenging activity. Compounds 8, 9, and 11a demonstrated significant NO inhibitory activity as compared to L-NAME and curcumin with IC50 values of 6.68 +/- A 0.16, 6.09 +/- A 0.46, and 6.84 +/- A 0.12 mu M, respectively. Apparently the suppression upon NO secretion was not due to cell death since the active compounds did not reduce the cell viability in close proximity to the IC50 of NO inhibition. Overall, incorporation of pyrazoline ring as part of the linker chain improved cell viability compared to the 2,6-bisbenzylidenecyclohexanone derivatives. Meanwhile, compound 11 (IC50 = 13.27 +/- A 1.78 mu M) bearing ortho hydroxyls on the aromatic rings recorded the highest radical scavenging activity as compared with quercetin (IC50 = 21.46 +/- A 0.85 mu M).
• Microwave-Assisted In Situ Cyclization of Curcumin Derivatives as Dominant Chemotherapeutic Agents for Leukemia and Colon Cancer
  作者：S. D. Hadiyal、J. N. Lalpara、B. B. Dhaduk

  DOI：10.1134/s1070428022030150

  日期：2022.3