2-(3-Methoxy-phenyl)-3-nitro-chromen-4-one | 143468-21-7

• 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: 2-(3-Methoxy-phenyl)-3-nitro-chromen-4-one
• 英文别名: 2-(3-Methoxyphenyl)-3-nitrochromen-4-one
• CAS: 143468-21-7
• 化学式: C₁₆H₁₁NO₅
• 分子量: 297.267
• InChiKey: MQVAZWJYMVOJBR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  81.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(3-Methoxy-phenyl)-3-nitro-chromen-4-one 在 palladium on activated charcoal 氢气 作用下， 以 1,4-二氧六环 为溶剂， 反应 16.0h， 以99%的产率得到3-amino-2-(3-methoxyphenyl)-4H-1-benzopyran-4-one
  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-chloro-3,4-dihydro-4-hydroxy-2-(3-methoxy-phenyl)-3-nitro-2H-1-benzopyran 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 8.33h， 生成 2-(3-Methoxy-phenyl)-3-nitro-chromen-4-one
  参考文献：
  名称：

  Synthesis of 2-Aryl-3-nitro-4H-1-benzopyran-4-ones

  摘要：

  2-Aryl-3-nitro-4H-1-benzopyran-4-ones (or 3-nitroflavones) 3 are conveniently prepared in good yields using a two-step approach starting from 2-aryl-3-chloro-3,4-dihydro-4-hydroxy-3-nitro-2H-1-benzopyrans 1. A general synthesis of the novel 2-aryl-3-chloro-2,3-dihydro-3-nitro-4H-1-benzopyran-4-ones 2 employed as intermediates in the procedure is described.

  DOI：

  10.1055/s-1992-26198

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 2-Aryl-3-nitro-4<i>H</i>-1-benzopyran-4-ones
  作者：Daniel Dauzonne、Cyrille Grandjean

  DOI：10.1055/s-1992-26198

  日期：——

  2-Aryl-3-nitro-4H-1-benzopyran-4-ones (or 3-nitroflavones) 3 are conveniently prepared in good yields using a two-step approach starting from 2-aryl-3-chloro-3,4-dihydro-4-hydroxy-3-nitro-2H-1-benzopyrans 1. A general synthesis of the novel 2-aryl-3-chloro-2,3-dihydro-3-nitro-4H-1-benzopyran-4-ones 2 employed as intermediates in the procedure is described.

  2-Aryl-3-nitro-4H-1-benzopyran-4-ones (or 3-nitroflavones) 3 are conveniently prepared in good yields using a two-step approach starting from 2-aryl-3-chloro-3,4-dihydro-4-hydroxy-3-nitro-2H-1-benzopyrans 1. A general synthesis of the novel 2-aryl-3-chloro-2,3-dihydro-3-nitro-4H-1-benzopyran-4-ones 2 employed as intermediates in the procedure is described.