3,11-dimethoxy-7,8-dihydro-6H-chromeno[3,2-d]xanthene

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 3,11-dimethoxy-7,8-dihydro-6H-chromeno[3,2-d]xanthene
• 英文别名: CHX-5MO-SAL；6,18-Dimethoxy-2,22-dioxapentacyclo[12.8.0.01,10.03,8.016,21]docosa-3(8),4,6,9,14,16(21),17,19-octaene；6,18-dimethoxy-2,22-dioxapentacyclo[12.8.0.01,10.03,8.016,21]docosa-3(8),4,6,9,14,16(21),17,19-octaene
• 化学式: C₂₂H₂₀O₄
• 分子量: 348.398
• InChiKey: FLVVZCAAAQVPIC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.84
• 重原子数：
  26.0
• 可旋转键数：
  2.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  36.92
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  2-羟基-5-甲氧基苯甲醛 、 环己酮 在 四氯化硅 、 ammonium hydroxide 作用下， 以 乙醇 、 乙醚 为溶剂， 以81%的产率得到3,11-dimethoxy-7,8-dihydro-6H-chromeno[3,2-d]xanthene
  参考文献：
  名称：

  SiCl₄mediated one-pot synthesis of novel spirobibenzopyrans as potent anticancer agents

  摘要：

  这项研究是关于未被开发利用的一类治疗剂——螺环联苯吡喃类化合物的抗癌活性的首次报告。

  DOI：

  10.1039/c8nj06444j

文献信息

• SiCl₄mediated one-pot synthesis of novel spirobibenzopyrans as potent anticancer agents
  作者：Swayamsiddha Kar、Naveen Shivalingegowda、Lokanath Neratur Krishnappagowda、Nageswara Rao Golakoti

  DOI：10.1039/c8nj06444j

  日期：——

  This study is the first report on the anticancer activity of spirobibenzopyrans, an unexplored class of therapeutic agents.

  这项研究是关于未被开发利用的一类治疗剂——螺环联苯吡喃类化合物的抗癌活性的首次报告。
• Synthesis of novel spirobibenzopyrans as potent anticancer leads inducing apoptosis in HeLa cells
  作者：Swayamsiddha Kar、Gayathri Ramamoorthy、Kartik Mitra、Naveen Shivalingegowda、Mahesha、Sai Kiran Mavileti、Lokanath Neratur Krishnappagowda、Mukesh Doble、Nageswara Rao Golakoti

  DOI：10.1016/j.bmcl.2020.127199

  日期：2020.6

  Spirobibenzopyrans are an unexplored class of therapeutics. We report the anticancer activity of novel spirobibenzopyrans, synthesized by a one-pot reaction and extensively characterized. Structure of one of the spirobibenzopyran has been determined by the single crystal XRD technique. The in vitro anticancer activity of these derivatives across the NCI 60-cell line panel was evaluated and for the first time their mechanism of action against HeLa cells was probed via cell morphology analysis and cell cycle analysis. They were determined to be apoptosis inducers with cell cycle arrest in G(0)/G(1) and S phase suggesting CDK-4 protein inhibition and the inhibition of DNA replication. The DNA inhibition was studied and confirmed using the alkaline comet assay for the compound CHX-4MO-SAL showing S phase inhibition. Further, conformity with the in silico Lipinski's score signify the potential of spirobibenzopyrans as anticancer leads.