(E)-1-(4-chloro-2-hydroxyphenyl)-3-(4-chlorophenyl)prop-2-en-1-one | 36768-43-1

• 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-(4-chloro-2-hydroxyphenyl)-3-(4-chlorophenyl)prop-2-en-1-one
• 英文别名: 4,4'-Dichlor-2'-hydroxychalcon
• CAS: 36768-43-1
• 化学式: C₁₅H₁₀Cl₂O₂
• 分子量: 293.149
• InChiKey: PVEXJEITSZPXNK-FPYGCLRLSA-N

物化性质

• 熔点：
  150-151 °C(Solv: ethanol (64-17-5); acetone (67-64-1))
• 沸点：
  464.2±45.0 °C(Predicted)
• 密度：
  1.381±0.06 g/cm3(Predicted)

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-(4-chloro-2-hydroxyphenyl)-3-(4-chlorophenyl)prop-2-en-1-one 在 水 、 sodium acetate 作用下， 以 乙醇 为溶剂， 以54%的产率得到7-chloro-2-(4-chlorophenyl)chroman-4-one
  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
• 作为产物：
  描述：

  4'-氯-2'-羟基苯乙酮 、 4-氯苯甲醛 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 48.0h， 以80%的产率得到(E)-1-(4-chloro-2-hydroxyphenyl)-3-(4-chlorophenyl)prop-2-en-1-one
  参考文献：
  名称：

  4'-Hydroxy-3-methoxyflavones with potent antipicornavirus activity

  摘要：

  4'-Hydroxy-3-methoxyflavones are natural compounds with known antiviral activities against picornaviruses such as poliomyelitis and rhinoviruses. In order to establish a structure-activity relationship a series of analogues were synthesized, and their antiviral activities and cytotoxicities were compared with those of flavones from natural origin. The 4'-hydroxyl and 3-methoxyl groups, a substitution in the 5 position and a polysubstituted A ring appeared to be essential requirements for a high activity. The most interesting compound was 4',7-dihydroxy-3-methoxy-5,6-dimethylflavone possessing in vitro TI99 values of > 1000 and > 200 against poliovirus type 1 and rhinovirus type 15, respectively. This compound was also active against other rhinovirus serotypes (2, 9, 14, 29, 39, 41, 59, 63, 70, 85, and 89) tested, having MIC50 values ranging from 0.016 to 0.5-mu-g/mL. Finally in contrast to quercetin it showed to be not mutagenic in concentrations up to 2.5 mg in the Ames test.

  DOI：

  10.1021/jm00106a039

文献信息

• 4'-Hydroxy-3-methoxyflavones with potent antipicornavirus activity
  作者：Nadine De Meyer、Achiel Haemers、Lallan Mishra、Hrishi Kesh Pandey、L. A. C. Pieters、Dirk A. Vanden Berghe、Arnold J. Vlietinck

  DOI：10.1021/jm00106a039

  日期：1991.2

  4'-Hydroxy-3-methoxyflavones are natural compounds with known antiviral activities against picornaviruses such as poliomyelitis and rhinoviruses. In order to establish a structure-activity relationship a series of analogues were synthesized, and their antiviral activities and cytotoxicities were compared with those of flavones from natural origin. The 4'-hydroxyl and 3-methoxyl groups, a substitution in the 5 position and a polysubstituted A ring appeared to be essential requirements for a high activity. The most interesting compound was 4',7-dihydroxy-3-methoxy-5,6-dimethylflavone possessing in vitro TI99 values of > 1000 and > 200 against poliovirus type 1 and rhinovirus type 15, respectively. This compound was also active against other rhinovirus serotypes (2, 9, 14, 29, 39, 41, 59, 63, 70, 85, and 89) tested, having MIC50 values ranging from 0.016 to 0.5-mu-g/mL. Finally in contrast to quercetin it showed to be not mutagenic in concentrations up to 2.5 mg in the Ames test.
• DE, MEYER NADINE;HAEMERS, ACHIEL;MISHRA, LALLAN;PANDEY, HRISHI-KESH;PIETE+, J. MED. CHEM., 34,(1991) N, C. 736-746
  作者：DE, MEYER NADINE、HAEMERS, ACHIEL、MISHRA, LALLAN、PANDEY, HRISHI-KESH、PIETE+

  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.