ovalitenone | 64280-22-4

• 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: ovalitenone
• 英文别名: 1-(1,3-benzodioxol-5-yl)-3-(4-methoxy-1-benzofuran-5-yl)propane-1,3-dione
• CAS: 64280-22-4
• 化学式: C₁₉H₁₄O₆
• 分子量: 338.317
• InChiKey: SDJBCBKWKASUCJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  75
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ovalitenone 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以72%的产率得到4H-呋喃并[2,3-h]-1-苯并吡喃-4-酮,2-(1,3-苯并二噁唑-5-基)-
  参考文献：
  名称：

  An efficient transformation of furano-hydroxychalcones to furanoflavones via base mediated intramolecular tandem O-arylation and C–O bond cleavage: a new approach for the synthesis of furanoflavones

  摘要：

  一种高效的将呋喃羟基茵黄酮转化为呋喃黄酮的方法，通过分子内串联O芳基化，随后进行C-O键断裂。

  DOI：

  10.1039/c5ob01802a

文献信息

• Furanoflavones pongapin and lanceolatin B blocks the cell cycle and induce senescence in CYP1A1-overexpressing breast cancer cells
  作者：Rajni Sharma、Ibidapo S. Williams、Linda Gatchie、Vinay R. Sonawane、Bhabatosh Chaudhuri、Sandip B. Bharate

  DOI：10.1016/j.bmc.2018.11.013

  日期：2018.12

  Expression of cytochrome P450-1A1 (CYP1A1) is suppressed under physiologic conditions but is induced (a) by polycyclic aromatic hydrocarbons (PAHs) which can be metabolized by CYP1A1 to carcinogens, and (b) in majority of breast cancers. Hence, phytochemicals or dietary flavonoids, if identified as CYP1A1 inhibitors, may help in preventing PAH-mediated carcinogenesis and breast cancer. Herein, we have investigated the cancer chemopreventive potential of a flavonoid-rich Indian medicinal plant, Pongamia pinnata (L.) Pierre. Methanolic extract of its seeds inhibits CYP1A1 in CYP1A1-overexpressing normal human HEK293 cells, with IC50 of 0.6 mu g/mL. Its secondary metabolites, the furanoflavonoids pongapin/lanceolatin B, inhibit CYP1A1 with IC50 of 20 nM. Although the furanochalcone pongamol inhibits CYP1A1 with IC50 of only 4.4 mu M, a semisynthetic pyrazole-derivative P5b, has similar to 10-fold improved potency (IC50, 0.49 mu M). Pongapin/lanceolatin B and the methanolic extract of P. pinnata seeds protect CYP1A1-overexpressing HEK293 cells from B[a] P-mediated toxicity. Remarkably, they also block the cell cycle of CYP1A1-overexpressing MCF-7 breast cancer cells, at the G(0)-G(1) phase, repress cyclin D1 levels and induce cellular-senescence. Molecular modeling studies demonstrate the interaction pattern of pongapin/lanceolatin B with CYP1A1. The results strongly indicate the potential of methanolic seed-extract and pongapin/lanceolatin B for further development as cancer chemopreventive agents.
• An efficient transformation of furano-hydroxychalcones to furanoflavones via base mediated intramolecular tandem O-arylation and C–O bond cleavage: a new approach for the synthesis of furanoflavones
  作者：Rajni Sharma、Ram A. Vishwakarma、Sandip B. Bharate

  DOI：10.1039/c5ob01802a

  日期：——

  An efficient transformation of furano-hydroxychalcones to furanoflavonesviaan intramolecular tandemO-arylation followed by C–O bond cleavage is described.

  一种高效的将呋喃羟基茵黄酮转化为呋喃黄酮的方法，通过分子内串联O芳基化，随后进行C-O键断裂。