3-nitro-4-oxo-2-phenyl-4H-1-benzopyran-8-acetic acid | 163977-81-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 3-nitro-4-oxo-2-phenyl-4H-1-benzopyran-8-acetic acid
• 英文别名: 2-(3-Nitro-4-oxo-2-phenylchromen-8-yl)acetic acid
• CAS: 163977-81-9
• 化学式: C₁₇H₁₁NO₆
• 分子量: 325.277
• InChiKey: UJLJKKPKBGCBNP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  109
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-nitro-4-oxo-2-phenyl-4H-1-benzopyran-8-acetic acid 在 palladium on activated charcoal 盐酸 、 硫酸 、 氢气 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 生成 2-(3-Amino-4-oxo-2-phenylchromen-8-yl)acetic acid;hydrochloride
  参考文献：
  名称：

  Synthesis and in vitro cytotoxicity of a series of 3-aminoflavones

  摘要：

  To further understand the molecular requirements for the antiproliferative activity of flavonoids, a series of 3-aminoflavones and some of their derivatives were prepared and evaluated using L1210 murine leukemia. Our novel five-step synthetic approach required easily available substituted aromatic aldehydes as starting materials and proved more convenient and more general than previously reported methods. Our results in the 3-aminoflavones series indicated that the 4'-methoxy group is important for cytotoxic activity. Moreover, for the flavone-8-acetic analogs, a marked increase in potency was observed with the addition of a 3-amino or a 3-nitro group, Methoxy groups on the 6 and 7 positions of flavonoids (as in cirsiliol) also appear to be important for antiproliferative activity. These results are essential for the further understanding of the critical molecular requirements that lead to antiproliferative properties in the flavonoid series.

  DOI：

  10.1016/s0223-5234(97)84363-2
• 作为产物：
  描述：

  3-nitro-2-phenyl-8-(prop-2-enyl)-4H-1-benzopyran-4-one 在 ruthenium trichloride 、 sodium periodate 作用下， 以 四氯化碳 、 水 、 乙腈 为溶剂， 以75%的产率得到3-nitro-4-oxo-2-phenyl-4H-1-benzopyran-8-acetic acid
  参考文献：
  名称：

  3-氨基黄酮-8-乙酸的合成

  摘要：

  从2-羟基-3-（丙酸）开始合成迄今未知的3-氨基-4-氧代-2-苯基-4 H -1-苯并吡喃-8-乙酸（3-氨基黄酮-8-乙酸）的合成描述了-2-烯）苯甲醛和（Z）-（2-氯-2-硝基乙烯基）苯。

  DOI：

  10.1016/0040-4039(95)00138-3

文献信息

• Synthesis and in vitro cytotoxicity of a series of 3-aminoflavones
  作者：D Dauzonne、B Folléas、L Martinez、GG Chabot

  DOI：10.1016/s0223-5234(97)84363-2

  日期：1997.1

  To further understand the molecular requirements for the antiproliferative activity of flavonoids, a series of 3-aminoflavones and some of their derivatives were prepared and evaluated using L1210 murine leukemia. Our novel five-step synthetic approach required easily available substituted aromatic aldehydes as starting materials and proved more convenient and more general than previously reported methods. Our results in the 3-aminoflavones series indicated that the 4'-methoxy group is important for cytotoxic activity. Moreover, for the flavone-8-acetic analogs, a marked increase in potency was observed with the addition of a 3-amino or a 3-nitro group, Methoxy groups on the 6 and 7 positions of flavonoids (as in cirsiliol) also appear to be important for antiproliferative activity. These results are essential for the further understanding of the critical molecular requirements that lead to antiproliferative properties in the flavonoid series.
• Synthesis of the 3-aminoflavone-8-acetic acid
  作者：Daniel Dauzonne、Laetitia Martinez

  DOI：10.1016/0040-4039(95)00138-3

  日期：1995.3

  The synthesis of the so far unknown 3-amino-4-oxo-2-phenyl-4H-1-benzopyran-8-acetic acid (3-aminoflavone-8-acetic acid) starting from 2-hydroxy-3-(prop-2-ene)benzaldehyde and (Z)-(2-chloro-2-nitroethenyl)benzene is described.

  从2-羟基-3-（丙酸）开始合成迄今未知的3-氨基-4-氧代-2-苯基-4 H -1-苯并吡喃-8-乙酸（3-氨基黄酮-8-乙酸）的合成描述了-2-烯）苯甲醛和（Z）-（2-氯-2-硝基乙烯基）苯。