5-羟基-6-硝基-2-苯基-苯并吡喃-4-酮 | 92424-80-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 中文名称: 5-羟基-6-硝基-2-苯基-苯并吡喃-4-酮
• 英文名称: 5-hydroxy-6-nitroflavone
• 英文别名: 6-Nitro-5-hydroxy-flavon；5-hydroxy-6-nitro-2-phenyl-chromen-4-one；5-Hydroxy-6-nitro-2-phenyl-chromen-4-on；5-Hydroxy-6-nitro-2-phenyl-4h-chromen-4-one；5-hydroxy-6-nitro-2-phenylchromen-4-one
• CAS: 92424-80-1
• 化学式: C₁₅H₉NO₅
• 分子量: 283.24
• InChiKey: WYRPSALLMOLFKE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  92.4
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 海关编码：
  2914700090

反应信息

• 作为反应物：
  描述：

  5-羟基-6-硝基-2-苯基-苯并吡喃-4-酮 在 溶剂黄146 、 锌 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以65%的产率得到6-氨基-5-羟基-2-苯基色烯-4-酮
  参考文献：
  名称：

  α-Glucosidase inhibition of 6-hydroxyflavones. Part 3: Synthesis and evaluation of 2,3,4-trihydroxybenzoyl-containing flavonoid analogs and 6-aminoflavones as α-glucosidase inhibitors

  摘要：

  The SAR studies suggested that the C-ring of baicalein (1) was not necessary for the activity, and validated the importance of 2,3,4-trihydroxybenzoyl structure of 1. Thus, a series of 2,3,4-trihydroxybenzoyi-containing flavonoid analogs were investigated for the alpha-glucosidase inhibitory activity. The results indicated that 5,6,7-trihydroxy-2-phenyl-4-quinolone (2) and 5,6,7-trihydroxyflavanone (4) showed the comparable activity to 1, while 3,5,6,7-tetrahydroxyflavone (7), 5,6,7-trihydroxyisoflavone (8), and 6-hydroxygenistein (9) showed moderate alpha-glucosidase inhibitory activity. In addition, it was found that 6-amino-5,7-dihydroxyflavone (16) was a more potent and specific rat intestinal alpha-glucosidase inhibitor than 1, and showed the comparable activity to acarbose. This is the first report on mammalian intestinal alpha-glucosidase inhibitory activity of 6-aminoflavones. Kinetic studies revealed that 16 inhibited both sucrose- and maltose-hydrolyzing activities of rat intestinal alpha-glucosidase uncompetitively/ (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.12.010
• 作为产物：
  描述：

  3-bromo-5-hydroxy-6-nitro-2-phenyl-chroman-4-one 在 吡啶 作用下， 生成 5-羟基-6-硝基-2-苯基-苯并吡喃-4-酮
  参考文献：
  名称：

  Reactions of Nitrohydroxychalcones: Synthesis of Nitrohydroxyflavones

  摘要：

  DOI：

  10.1021/jo01105a042

文献信息

• Naik; Thakor, Proceedings - Indian Academy of Sciences, Section A, 1953, # 37, p. 774,777
  作者：Naik、Thakor

  DOI：——

  日期：——
• Naik et al., Proceedings - Indian Academy of Sciences, Section A, 1953, # 38, p. 31,35
  作者：Naik et al.

  DOI：——

  日期：——
• Naik; Thakor, Proceedings - Indian Academy of Sciences, Section A, p. 37 >1953> 774, 778
  作者：Naik、Thakor

  DOI：——

  日期：——
• α-Glucosidase inhibition of 6-hydroxyflavones. Part 3: Synthesis and evaluation of 2,3,4-trihydroxybenzoyl-containing flavonoid analogs and 6-aminoflavones as α-glucosidase inhibitors
  作者：Hong Gao、Jun Kawabata

  DOI：10.1016/j.bmc.2004.12.010

  日期：2005.3.1

  The SAR studies suggested that the C-ring of baicalein (1) was not necessary for the activity, and validated the importance of 2,3,4-trihydroxybenzoyl structure of 1. Thus, a series of 2,3,4-trihydroxybenzoyi-containing flavonoid analogs were investigated for the alpha-glucosidase inhibitory activity. The results indicated that 5,6,7-trihydroxy-2-phenyl-4-quinolone (2) and 5,6,7-trihydroxyflavanone (4) showed the comparable activity to 1, while 3,5,6,7-tetrahydroxyflavone (7), 5,6,7-trihydroxyisoflavone (8), and 6-hydroxygenistein (9) showed moderate alpha-glucosidase inhibitory activity. In addition, it was found that 6-amino-5,7-dihydroxyflavone (16) was a more potent and specific rat intestinal alpha-glucosidase inhibitor than 1, and showed the comparable activity to acarbose. This is the first report on mammalian intestinal alpha-glucosidase inhibitory activity of 6-aminoflavones. Kinetic studies revealed that 16 inhibited both sucrose- and maltose-hydrolyzing activities of rat intestinal alpha-glucosidase uncompetitively/ (C) 2004 Elsevier Ltd. All rights reserved.
• Reactions of Nitrohydroxychalcones: Synthesis of Nitrohydroxyflavones
  作者：S. SESHADRI、P. L. TRIVEDI

  DOI：10.1021/jo01105a042

  日期：1958.11