2-(4-nitrophenoxy)-1-phenyl-propan-1-one | 101097-75-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(4-nitrophenoxy)-1-phenyl-propan-1-one
• 英文别名: 2-(4-nitro-phenoxy)-1-phenyl-propan-1-one；2-(4-Nitro-phenoxy)-1-phenyl-propan-1-on；(p-Nitrophenoxy)propiophenone；2-(4-nitrophenoxy)-1-phenylpropan-1-one
• CAS: 101097-75-0
• 化学式: C₁₅H₁₃NO₄
• 分子量: 271.273
• InChiKey: FBLBJILLEMJSIL-UHFFFAOYSA-N

物化性质

• 熔点：
  82-83 °C
• 沸点：
  447.2±25.0 °C(Predicted)
• 密度：
  1.243±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  苯丙酮 在 溴 、 potassium carbonate 作用下， 以 氯仿 、 丁酮 为溶剂， 反应 2.25h， 生成 2-(4-nitrophenoxy)-1-phenyl-propan-1-one
  参考文献：
  名称：

  Synthesis, Characterization and in vitro Anticancer Activity of Novel 8,4’-Oxyneolignan Analogues

  摘要：

  Neolignans are a class of natural products with a wide range of biological effects. These substances are of great synthetic and biological interest, especially in searching for novel anticancer agents. In this paper, we report the synthesis of a new subclass of 8,4'-oxyneolignan analogues (beta-ketoethers and beta-ketoesters) and their cell viability assay on twenty four different cancer cells, among leukemias and carcinomas. Three compounds inhibited the growth of most human cancer cells. 2-Oxo-2-phenylethyl(2E)-3-[4-(2-oxo-2-phenylethoxy) phenyl] prop-2-enoate showed an antiproliferative activity superior to doxorubicin for U-87, U-138 MG and H1299 cell types and (E)-2-oxo-2-phenylethyl 3-(3-methoxy-4-(2-oxo-2-phenylethoxy) phenyl) acrylate was found to be very selective, demonstrating a growth inhibition of 92.0% against KG-1 cells. Furthermore, 1-oxo-1-phenylpropan-2-yl cinnamate exhibited significant inhibition activity in a range of 52.2 to 91.2% against twelve kinds of leukemia cell lines, revealing excellent results and very comparable to the reference drug.

  DOI：

  10.21577/0103-5053.20170075

文献信息

• Samochwalow et al., Zhurnal Obshchei Khimii, 1957, vol. 27, p. 2501,2505; engl. Ausg. S. 2560, 2563
  作者：Samochwalow et al.

  DOI：——

  日期：——
• Synthesis, Characterization and in vitro Anticancer Activity of Novel 8,4’-Oxyneolignan Analogues
  作者：Gisele Souza、Gilberto Franchi Jr.、Alexandre Nowill、Lourivaldo Santos、Cláudio Alves、Lauro Barata、Carlos Andrade

  DOI：10.21577/0103-5053.20170075

  日期：——

  Neolignans are a class of natural products with a wide range of biological effects. These substances are of great synthetic and biological interest, especially in searching for novel anticancer agents. In this paper, we report the synthesis of a new subclass of 8,4'-oxyneolignan analogues (beta-ketoethers and beta-ketoesters) and their cell viability assay on twenty four different cancer cells, among leukemias and carcinomas. Three compounds inhibited the growth of most human cancer cells. 2-Oxo-2-phenylethyl(2E)-3-[4-(2-oxo-2-phenylethoxy) phenyl] prop-2-enoate showed an antiproliferative activity superior to doxorubicin for U-87, U-138 MG and H1299 cell types and (E)-2-oxo-2-phenylethyl 3-(3-methoxy-4-(2-oxo-2-phenylethoxy) phenyl) acrylate was found to be very selective, demonstrating a growth inhibition of 92.0% against KG-1 cells. Furthermore, 1-oxo-1-phenylpropan-2-yl cinnamate exhibited significant inhibition activity in a range of 52.2 to 91.2% against twelve kinds of leukemia cell lines, revealing excellent results and very comparable to the reference drug.