2-(4-hydroxy-3-methoxybenzylidene)-2,3-dihydro-5,6-dimethoxyinden-1-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 2-(4-hydroxy-3-methoxybenzylidene)-2,3-dihydro-5,6-dimethoxyinden-1-one
• 英文别名: 2-(4-hydroxy-3-methoxybenzylidene)-5,6-dimethoxy-2,3-dihydro-1H-inden-1-one；2-[(4-hydroxy-3-methoxyphenyl)methylidene]-5,6-dimethoxy-3H-inden-1-one
• 化学式: C₁₉H₁₈O₅
• 分子量: 326.349
• InChiKey: FLMBUHUCBMHMRZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(4-hydroxy-3-methoxybenzylidene)-2,3-dihydro-5,6-dimethoxyinden-1-one 在 palladium on activated charcoal 、 氢气 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 以70%的产率得到2-(4-hydroxy-3-methoxybenzyl)-2,3-dihydro-5,6-dimethoxyinden-1-one
  参考文献：
  名称：

  Syntheses of 2-methoxyestradiol and eugenol template based diarylpropenes as non-steroidal anticancer agents

  摘要：

  基于2-甲氧基雌二醇（1）和丁子香酚（6）模板，合成了构象灵活和刚性的二芳基丙烯类化合物14(a–l)与20(a–e)，作为非甾体抗肿瘤药物。采用SRB法评估了这些合成化合物在体外对人癌细胞系MCF-7、A549、DU 145、KB和MDA-MB-231的抗肿瘤活性。化合物14i、14k和15a在不同癌细胞系中显示显著的抗肿瘤活性，IC50值介于10.27 μM至27.91 μM之间。活性最高的分子14k通过诱导凋亡和阻滞细胞周期于G2/M期来抑制细胞增殖。在正常肝单核细胞（THP-1）中进行的体外毒性测试显示，这些化合物（14i、14k和15a）对癌细胞与健康细胞具有高度的选择性。

  DOI：

  10.1039/c4ra03823a
• 作为产物：
  描述：

  3-甲氧基-4-[(四氢-2H-吡喃-2-基)氧基]苯甲醛 在 盐酸 、 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 5.0h， 生成 2-(4-hydroxy-3-methoxybenzylidene)-2,3-dihydro-5,6-dimethoxyinden-1-one
  参考文献：
  名称：

  2-亚苄基-1-茚满酮衍生物的设计、合成和构效关系作为治疗急性肺损伤的抗炎剂

  摘要：

  Purpose: The purpose of this study was to design and synthesize novel 2-benzylidene-1-indanone derivatives for treatment of acute lung injury.Methods: A series of 39 novel 2-benzylidene-indanone structural derivatives were synthesized and evaluated for anti-inflammatory activity in lipopolysaccharide (LPS)-stimulated murine primary macrophages.Results: Most of the obtained compounds effectively inhibited the LPS-induced expression of IL-6 and TNF-alpha. The most active compound, 8f, was found to significantly reduce LPS-induced pulmonary inflammation, as reflected by reductions in the concentration of total protein, inflammatory cell count, as well as the lung wet/dry ratio in bronchoalveolar lavage (BAL) fluid. Furthermore, 8f effectively inhibited mRNA expression of several inflammatory cytokines after LPS challenge in vitro and in vivo. Administration of 8f also blocked LPS-induced activation of the proinflammatory NF-kappa B/MAPK signaling pathway.Conclusion: The simple synthetic preparation and biological properties of these derivatives make these 2-benzylidene-indanone scaffolds promising new entities for the development of anti-inflammatory therapeutics for the treatment of acute lung injury.

  DOI：

  10.2147/dddt.s160314

文献信息

• Design, synthesis, and structure–activity relationships of 2-benzylidene-1-indanone derivatives as anti-inflammatory agents for treatment of acute lung injury
  作者：Siyang Xiao、Wenxin Zhang、Hongjin Chen、Bo Fang、Yinda Qiu、Xianxin Chen、Lingfeng Chen、Shen Shu、Yali Zhang、Yunjie Zhao、Zhiguo Liu、Guang Liang

  DOI：10.2147/dddt.s160314

  日期：——

  Purpose: The purpose of this study was to design and synthesize novel 2-benzylidene-1-indanone derivatives for treatment of acute lung injury.Methods: A series of 39 novel 2-benzylidene-indanone structural derivatives were synthesized and evaluated for anti-inflammatory activity in lipopolysaccharide (LPS)-stimulated murine primary macrophages.Results: Most of the obtained compounds effectively inhibited the LPS-induced expression of IL-6 and TNF-alpha. The most active compound, 8f, was found to significantly reduce LPS-induced pulmonary inflammation, as reflected by reductions in the concentration of total protein, inflammatory cell count, as well as the lung wet/dry ratio in bronchoalveolar lavage (BAL) fluid. Furthermore, 8f effectively inhibited mRNA expression of several inflammatory cytokines after LPS challenge in vitro and in vivo. Administration of 8f also blocked LPS-induced activation of the proinflammatory NF-kappa B/MAPK signaling pathway.Conclusion: The simple synthetic preparation and biological properties of these derivatives make these 2-benzylidene-indanone scaffolds promising new entities for the development of anti-inflammatory therapeutics for the treatment of acute lung injury.
• Syntheses of 2-methoxyestradiol and eugenol template based diarylpropenes as non-steroidal anticancer agents
  作者：Vinay Pathak、Imran Ahmad、Amandeep Kaur Kahlon、Mohammad Hasanain、Sandeep Sharma、Kishore K. Srivastava、Jayanta Sarkar、Karuna Shankar、Ashok Sharma、Atul Gupta

  DOI：10.1039/c4ra03823a

  日期：——

  Syntheses of 2-methoxyestradiol (1) and eugenol (6) template based conformationally flexible and rigid diarylpropenes, 14(a–l) and 20(a–e), as nonsteroidal anticancer agents have been performed. The synthesized compounds were evaluated for their anticancer activity in in vitro using a panel of human cancer cell lines viz. MCF-7, A549, DU 145, KB and MDA-MB-231by SRB assay. Compounds 14i, 14k and 15a showed significant anticancer activity at IC50 between 10.27 μM to 27.91 μM in different cancer cell lines. The most active molecule, 14k, inhibited proliferation of cells by inducing apoptosis and arresting the cell cycle at the G2/M phase. In vitro toxicity of these compounds (14i, 14k and 15a) in healthy hepatic monocyte (THP-1) cells showed high selectivity of compounds towards cancerous vs. healthy cells.

  基于2-甲氧基雌二醇（1）和丁子香酚（6）模板，合成了构象灵活和刚性的二芳基丙烯类化合物14(a–l)与20(a–e)，作为非甾体抗肿瘤药物。采用SRB法评估了这些合成化合物在体外对人癌细胞系MCF-7、A549、DU 145、KB和MDA-MB-231的抗肿瘤活性。化合物14i、14k和15a在不同癌细胞系中显示显著的抗肿瘤活性，IC50值介于10.27 μM至27.91 μM之间。活性最高的分子14k通过诱导凋亡和阻滞细胞周期于G2/M期来抑制细胞增殖。在正常肝单核细胞（THP-1）中进行的体外毒性测试显示，这些化合物（14i、14k和15a）对癌细胞与健康细胞具有高度的选择性。