2-(2,4-dichlorophenyl)-5-(4-methoxybenzofuran-5-yl)-3-phenyl-2H-pyrazole | 1286238-27-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(2,4-dichlorophenyl)-5-(4-methoxybenzofuran-5-yl)-3-phenyl-2H-pyrazole
• 英文别名: 1-(2,4-dichlorophenyl)-3-(4-methoxybenzofuran-5-yl)-5-phenyl-1H-pyrazole；1-(2,4-Dichlorophenyl)-3-(4-methoxy-1-benzofuran-5-yl)-5-phenylpyrazole；1-(2,4-dichlorophenyl)-3-(4-methoxy-1-benzofuran-5-yl)-5-phenylpyrazole
• CAS: 1286238-27-4
• 化学式: C₂₄H₁₆Cl₂N₂O₂
• 分子量: 435.309
• InChiKey: KCHRQISXLDQSJN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  40.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  水黄皮籽素 、 2,4-二氯苯肼盐酸盐 在 溶剂黄146 作用下， 反应 8.0h， 以55%的产率得到2-(2,4-dichlorophenyl)-5-(4-methoxybenzofuran-5-yl)-3-phenyl-2H-pyrazole
  参考文献：
  名称：

  Synthesis and anticancer effects of pongamol derivatives on mitogen signaling and cell cycle kinases

  摘要：

  A series of oxazole and pyrazole derivatives of pongamol (1) were designed and synthesized to examine their anti-cancer activity. The cytotoxicity of these compounds was examined in three different human tumor cell lines, IMR-32, HeLa and Jurkat. Although all compounds tested were quite effective than the pongamol against all the three different types of cancer cell lines examined, the compounds (2), (5), and (6) were found to be the most active compounds of this series.

  DOI：

  10.1007/s00044-011-9563-y

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.