(E)-7-hydroxy-4-methyl-2-oxo-10-(3-oxo-3-p-tolylprop-1-enyl)-2H-benzo[h]chromene-8-carbaldehyde | 1259925-35-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (E)-7-hydroxy-4-methyl-2-oxo-10-(3-oxo-3-p-tolylprop-1-enyl)-2H-benzo[h]chromene-8-carbaldehyde
• 英文别名: 7-hydroxy-4-methyl-2-oxo-10-(3-oxo-3-p-tolylpropenyl)-2H-benzo[h]chromene-8-carbaldehyde；7-hydroxy-4-methyl-10-[(E)-3-(4-methylphenyl)-3-oxoprop-1-enyl]-2-oxobenzo[h]chromene-8-carbaldehyde
• CAS: 1259925-35-3
• 化学式: C₂₅H₁₈O₅
• 分子量: 398.415
• InChiKey: RXIUCUYTSITNNT-JXMROGBWSA-N

物化性质

• 熔点：
  254-255 °C
• 沸点：
  650.6±55.0 °C(predicted)
• 密度：
  1.346±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  80.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (E)-7-hydroxy-4-methyl-2-oxo-10-(3-oxo-3-p-tolylprop-1-enyl)-2H-benzo[h]chromene-8-carbaldehyde 、 丙二酸二甲酯 在 哌啶 作用下， 以 乙醇 为溶剂， 反应 0.5h， 以79%的产率得到(E)-methyl 7-methyl-3,9-dioxo-11-(3-oxo-3-p-tolylprop-1-enyl)-3,9-dihydrochromeno[8,7-h]chromene-2-carboxylate
  参考文献：
  名称：

  Synthesis and anti-inflammatory activity of novel biscoumarin–chalcone hybrids

  摘要：

  A series of synthesized novel biscoumarin-chalcone hybrids were evaluated for their anti-inflammatory and antioxidant activity. The tested compounds significantly inhibit the carrageenin induced paw oedema in albino rats and also exhibit important scavenging activities. These compounds thus constitute an interesting template for the design of new therapeutic tools against inflammation. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.06.002
• 作为产物：
  描述：

  1,5-二羟基萘 在 盐酸 、 对甲苯磺酸 、 三氟乙酸 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 18.0h， 生成 (E)-7-hydroxy-4-methyl-2-oxo-10-(3-oxo-3-p-tolylprop-1-enyl)-2H-benzo[h]chromene-8-carbaldehyde
  参考文献：
  名称：

  Synthesis and anti-inflammatory activity of novel biscoumarin–chalcone hybrids

  摘要：

  A series of synthesized novel biscoumarin-chalcone hybrids were evaluated for their anti-inflammatory and antioxidant activity. The tested compounds significantly inhibit the carrageenin induced paw oedema in albino rats and also exhibit important scavenging activities. These compounds thus constitute an interesting template for the design of new therapeutic tools against inflammation. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.06.002

文献信息

• Neo-tanshinlactone inspired synthesis, in vitro evaluation of novel substituted benzocoumarin derivatives as potent anti-breast cancer agents
  作者：Koneni V. Sashidhara、Jammikuntla N. Rosaiah、Manoj Kumar、Rishi Kumar Gara、Lakshma Vadithe Nayak、Kamini Srivastava、Hemant Kumar Bid、Rituraj Konwar

  DOI：10.1016/j.bmcl.2010.09.040

  日期：2010.12

  A small library of novel benzocoumarin derivatives based on naturally occurring neo-tanshinlactone scaffold was constructed and their antiproliferative activities against breast cancer cells MCF-7 and MDA-MB-231 were evaluated. A number of derivatives showed good anti-breast cancer activity, in some cases higher to that of the reference compound tamoxifen. In particular, benzocoumarins Bc-5, Bc-8 and Bc-9 strongly inhibited the proliferation of MCF-7 cancer cell line with the IC50 values of 3.8, 7.9 and 6.5 mu M, respectively. The compounds were capable of inducing nuclear fragmentation, cell cycle arrest and caspase dependent apoptosis in MCF-7 cell lines. In addition, these derivatives were devoid of cytotoxic effect against normal osteoblast cells. These synthetic benzocoumarins hold promises for developing safer alternative to the existing anti-breast cancer agents. (C) 2010 Elsevier Ltd. All rights reserved.
• Synthesis and anti-inflammatory activity of novel biscoumarin–chalcone hybrids
  作者：Koneni V. Sashidhara、Manoj Kumar、Ram K. Modukuri、Ravi Sonkar、Gitika Bhatia、A.K. Khanna、Shivika Rai、Rakesh Shukla

  DOI：10.1016/j.bmcl.2011.06.002

  日期：2011.8

  A series of synthesized novel biscoumarin-chalcone hybrids were evaluated for their anti-inflammatory and antioxidant activity. The tested compounds significantly inhibit the carrageenin induced paw oedema in albino rats and also exhibit important scavenging activities. These compounds thus constitute an interesting template for the design of new therapeutic tools against inflammation. (C) 2011 Elsevier Ltd. All rights reserved.