2-(isopropylaminomethylene)-8-methyl-1,6-dioxo-1,2,5,6-tetrahydrophenanthrene-4-carbaldehyde | 933774-94-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: 2-(isopropylaminomethylene)-8-methyl-1,6-dioxo-1,2,5,6-tetrahydrophenanthrene-4-carbaldehyde
• 英文别名: 4-methyl-2,7-dioxo-8-[(propan-2-ylamino)methylidene]benzo[h]chromene-10-carbaldehyde
• CAS: 933774-94-8
• 化学式: C₁₉H₁₇NO₄
• 分子量: 323.348
• InChiKey: CYMOHBNNNKMSSG-UHFFFAOYSA-N

物化性质

• 熔点：
  240 °C
• 沸点：
  568.1±50.0 °C(predicted)
• 密度：
  1.371±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.76
• 重原子数：
  24.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  76.38
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  7-hydroxy-4-methyl-2-oxo-2H-benzo[h]chromen-8,10-dicarbaldehyde 、 异丙胺 以 乙醇 为溶剂， 反应 0.17h， 以85%的产率得到2-(isopropylaminomethylene)-8-methyl-1,6-dioxo-1,2,5,6-tetrahydrophenanthrene-4-carbaldehyde
  参考文献：
  名称：

  Neo-tanshinlactone inspired synthesis, in vitro evaluation of novel substituted benzocoumarin derivatives as potent anti-breast cancer agents

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2010.09.040

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.