4'-methylflavone-8-carboxylic acid | 92606-13-8

• 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: 4'-methylflavone-8-carboxylic acid
• 英文别名: 2-(4-Methylphenyl)-4-oxochromene-8-carboxylic acid
• CAS: 92606-13-8
• 化学式: C₁₇H₁₂O₄
• 分子量: 280.28
• InChiKey: XHQQHAGSLHXDPC-UHFFFAOYSA-N

物化性质

• 沸点：
  491.5±45.0 °C(Predicted)
• 密度：
  1.346±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  21
• 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：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4'-methylflavone-8-carboxylic acid chloride 、 N,N-二乙基乙二胺 、 4'-methylflavone-8-carboxylic acid 在 氯化亚砜 作用下， 以 苯 为溶剂， 生成 N-(2-Diethylaminoethyl)-4'-methylflavone-8-carboxamide
  参考文献：
  名称：

  N-substituted flavone-8-carboxamides

  摘要：

  式(I)所表示的N-取代黄酮-8-甲酰胺衍生物，其中R1表示氢原子、甲基或乙基，R2表示氢原子、低级烷基、低级烷氧基、卤素原子或硝基，R3表示氢原子或低级烷基，k表示0、1、2或3，m表示0或1；X和Y必须不同，表示氢原子或甲基。A表示具有式(II)的氨基，其中，R4和R5可以相同或不同，表示低级烷基或与氮原子一起形成的有或无氧原子的环状氨基，R6表示低级烷基，n表示2或3。这些衍生物以及含有它们的药物组合物和使用它们的治疗方法被公开。N-取代黄酮-8-甲酰胺衍生物作为治疗尿潴留的药物是有用的。

  公开号：

  US04525356A1
• 作为产物：
  描述：

  5-溴水杨酸 在 palladium on activated charcoal 氢氧化钾 、 三氯化铝 、 selenium(IV) oxide 、 硫酸 、 氢气 作用下， 以 1,4-二氧六环 、 乙醇 、 二甲基亚砜 为溶剂， 25.0~160.0 ℃ 、1.52 MPa 条件下， 反应 126.0h， 生成 4'-methylflavone-8-carboxylic acid
  参考文献：
  名称：

  Synthesis of carboxylated flavonoids as new leads for LTD4 antagonists

  摘要：

  A series of 3'- and 5'-carboxylated chalcones, 6- or 8-carboxylated flavones and 6-carboxylated flavanones, -flavanols and -flavans were prepared. The compounds were tested for their inhibitory activities against leukotriene D-4 (LTD(4)) induced contraction of guinea-pig ileum. A new and convenient synthetic route to 3-acetyl-2-hydroxybenzoic acid (1d), a key intermediate for the synthesis of 3'-carboxy-2'-hydroxychalcones and 8-carboxylated flavones, was developed. The activities of the tested compounds ranged from 0 to 63% inhibition at 10(-5) M drug concentration against a single challenge of 10(-8) M LTD(4). Several compounds were tested in a radioligand binding assay against [H-3]LTD(4) on guinea-pig lung membrane. The quinoline-containing chalcone 12 and flavone 17 were found to exhibit significant but weak affinities for LTD(4) receptors with pK(D)-values of 4.95 and 4.83, respectively, and are interesting lead structures for the development of rigid LTD(4) antagonists. In contrast, the rest of the compounds tested in the binding assay did not show significant displacement of the radioligand, implying that for these compounds the functional activity is probably not caused by competitive antagonism at the LTD(4) receptor. The exact mechanism of the relaxant activity remains unclear.

  DOI：

  10.1016/s0223-5234(97)89849-2

文献信息

• US4525356A
  申请人：——

  公开号：US4525356A

  公开（公告）日：1985-06-25
• Synthesis of carboxylated flavonoids as new leads for LTD4 antagonists
  作者：ME Zwaagstra、H Timmerman、RS Abdoelgafoer、MQ Zhang

  DOI：10.1016/s0223-5234(97)89849-2

  日期：1996.1

  A series of 3'- and 5'-carboxylated chalcones, 6- or 8-carboxylated flavones and 6-carboxylated flavanones, -flavanols and -flavans were prepared. The compounds were tested for their inhibitory activities against leukotriene D-4 (LTD(4)) induced contraction of guinea-pig ileum. A new and convenient synthetic route to 3-acetyl-2-hydroxybenzoic acid (1d), a key intermediate for the synthesis of 3'-carboxy-2'-hydroxychalcones and 8-carboxylated flavones, was developed. The activities of the tested compounds ranged from 0 to 63% inhibition at 10(-5) M drug concentration against a single challenge of 10(-8) M LTD(4). Several compounds were tested in a radioligand binding assay against [H-3]LTD(4) on guinea-pig lung membrane. The quinoline-containing chalcone 12 and flavone 17 were found to exhibit significant but weak affinities for LTD(4) receptors with pK(D)-values of 4.95 and 4.83, respectively, and are interesting lead structures for the development of rigid LTD(4) antagonists. In contrast, the rest of the compounds tested in the binding assay did not show significant displacement of the radioligand, implying that for these compounds the functional activity is probably not caused by competitive antagonism at the LTD(4) receptor. The exact mechanism of the relaxant activity remains unclear.
• N-substituted flavone-8-carboxamides
  申请人：Hokuriku Pharmaceutical Co., Ltd.

  公开号：US04525356A1

  公开（公告）日：1985-06-25

  Derivatives of N-substituted flavone-8-carboxamides represented by general formula (I) ##STR1## wherein R.sub.1 represents a hydrogen atom, a methyl group or an ethyl group, R.sub.2 represents a hydrogen atom, a lower alkyl group, a lower alkoxyl group, a halogen atom or a nitro group, R.sub.3 represents a hydrogen atom or a lower alkyl group, k represents 0, 1, 2, or 3, m represents 0 or 1; X and Y, which must be different, represent a hydrogen atom or methyl group. A represents an amino group having the formula ##STR2## wherein, R.sub.4 and R.sub.5, which may be the same or different, represent a lower alkyl group or a cyclic amino group together with the nitrogen atom and with or without an oxygen atom, R.sub.6 represents a lower alkyl group and n represents 2 or 3, are disclosed, as well as pharmaceutical compositions thereof and method of treating therewith. The N-substituted flavone-8-carboxamides derivatives are useful as agents for treatment of dysurea.

  式(I)所表示的N-取代黄酮-8-甲酰胺衍生物，其中R1表示氢原子、甲基或乙基，R2表示氢原子、低级烷基、低级烷氧基、卤素原子或硝基，R3表示氢原子或低级烷基，k表示0、1、2或3，m表示0或1；X和Y必须不同，表示氢原子或甲基。A表示具有式(II)的氨基，其中，R4和R5可以相同或不同，表示低级烷基或与氮原子一起形成的有或无氧原子的环状氨基，R6表示低级烷基，n表示2或3。这些衍生物以及含有它们的药物组合物和使用它们的治疗方法被公开。N-取代黄酮-8-甲酰胺衍生物作为治疗尿潴留的药物是有用的。