(E)-1-(5-Chloro-2-hydroxy-phenyl)-3-(3-chloro-phenyl)-propenone | 86881-94-9

• 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)-1-(5-Chloro-2-hydroxy-phenyl)-3-(3-chloro-phenyl)-propenone
• 英文别名: 1-(5-Chloro-2-hydroxyphenyl)-3-(3-chlorophenyl)prop-2-en-1-one；1-(5-chloro-2-hydroxyphenyl)-3-(3-chlorophenyl)prop-2-en-1-one
• CAS: 86881-94-9
• 化学式: C₁₅H₁₀Cl₂O₂
• 分子量: 293.149
• InChiKey: ZIQVOGGFHZSARK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-1-(5-Chloro-2-hydroxy-phenyl)-3-(3-chloro-phenyl)-propenone 在 水 、 sodium acetate 作用下， 以 乙醇 为溶剂， 以58%的产率得到3',6-Dichloroflavanone
  参考文献：
  名称：

  Halogenated flavanones as potential apoptosis-inducing agents: Synthesis and biological activity evaluation

  摘要：

  A series of halogenated flavanones were synthesized from 2-hydroxychalcones and tested for their cytotoxicity against a panel of human cancer cell lines. Among the synthesized compounds, 3',7-dichloroflavanone (2d) showed the highest activity against MCF-7, LNCaP, PO, Hep-G2, KB and SK-N-MC cells. However, 3',6-dichloroflavanone (2g) with IC50 value of 2.9 +/- 0.9 mu M was the most potent compound against MDA-MB-231 cells, being approximately 12 times more active than etoposide as reference drug. According to the flow-cytometric analysis, compound 2g can induce apoptosis by 66.19 and 21.37% in PO and MDA-MB-231 cells, respectively. The results of acridine orange/ethidium bromide staining and TUNEL assay suggested that the cytotoxic activity of this compound in PO and MDA-MB-231 cells occurs via apoptosis. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.10.043

文献信息

• Jadhav, K. P.; Ingle, D. B., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1983, vol. 22, # 2, p. 180 - 182
  作者：Jadhav, K. P.、Ingle, D. B.

  DOI：——

  日期：——
• Halogenated flavanones as potential apoptosis-inducing agents: Synthesis and biological activity evaluation
  作者：Maliheh Safavi、Nasim Esmati、Sussan Kabudanian Ardestani、Saeed Emami、Soheila Ajdari、Jamshid Davoodi、Abbas Shafiee、Alireza Foroumadi

  DOI：10.1016/j.ejmech.2012.10.043

  日期：2012.12

  A series of halogenated flavanones were synthesized from 2-hydroxychalcones and tested for their cytotoxicity against a panel of human cancer cell lines. Among the synthesized compounds, 3',7-dichloroflavanone (2d) showed the highest activity against MCF-7, LNCaP, PO, Hep-G2, KB and SK-N-MC cells. However, 3',6-dichloroflavanone (2g) with IC50 value of 2.9 +/- 0.9 mu M was the most potent compound against MDA-MB-231 cells, being approximately 12 times more active than etoposide as reference drug. According to the flow-cytometric analysis, compound 2g can induce apoptosis by 66.19 and 21.37% in PO and MDA-MB-231 cells, respectively. The results of acridine orange/ethidium bromide staining and TUNEL assay suggested that the cytotoxic activity of this compound in PO and MDA-MB-231 cells occurs via apoptosis. (C) 2012 Elsevier Masson SAS. All rights reserved.