5,7-bis(phenylmethoxy)-2-(4-phenylmethoxyphenyl)-2H-chromene | 859871-18-4

• 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: 5,7-bis(phenylmethoxy)-2-(4-phenylmethoxyphenyl)-2H-chromene
• CAS: 859871-18-4
• 化学式: C₃₆H₃₀O₄
• 分子量: 526.632
• InChiKey: PFEFNBMAAHVYMB-UHFFFAOYSA-N

物化性质

• 沸点：
  705.0±60.0 °C(Predicted)
• 密度：
  1.199±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  40
• 可旋转键数：
  10
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5,7-bis(phenylmethoxy)-2-(4-phenylmethoxyphenyl)-2H-chromene 在 硼烷四氢呋喃络合物 、 sodium hydroxide 、 双氧水 作用下， 生成 5,7-bis(phenylmethoxy)-2-(4-phenylmethoxyphenyl)-3,4-dihydro-2H-chromen-3-ol
  参考文献：
  名称：

  A structure-activity study for the inhibition of metalloproteinase-9 activity and gene expression by analogues of gallocatechin-3-gallate

  摘要：

  Catechins are able to modulate the gelatinolytic activity of matrix metalloproteinase-9 (MMP-9) by reducing its release from macrophages. Gallocatechins decrease MMP-9 secretion by lowering MMP-9 promoter activity and mRNA levels. The effect appears to be dependent on some structural and stereochemical requirements. In this study, the relationship between chemical structure and activity was studied by testing the effect of analogues of (+/-)-gallocatechin-3-gallate (+/-)-GCG, selectively deprived of hydroxyl groups, on MMP-9 activity, transcription, and secretion. Our results indicate that (+/-)-GCG and (+/-)-catechin-3-gallate are characterized by a substitution pattern compatible with direct inhibition of MMP-9 activity. Conversely, when transcription was the target, (+/-)-trans-3-flavanol-3-benzoate, lacking all the hydroxyl groups, was the most effective both in lowering MMP-9 promoter activity and consequently protein secretion, and in inhibiting nuclear-factor-kappa B-driven transcription. Our results suggest that the structural requirements for enzyme inhibition are different from those necessary for targeting gene expression.

  DOI：

  10.1007/s00018-005-5422-7
• 作为产物：
  描述：

  E-3-(4-苄氧基)-1-(2.4-二苄氧基-6-羟基)苯基)丙烯酮 在 sodium tetrahydroborate 、 三氟化硼乙醚 作用下， 以 二氯甲烷 、 乙二醇甲醚 为溶剂， 反应 0.66h， 生成 5,7-bis(phenylmethoxy)-2-(4-phenylmethoxyphenyl)-2H-chromene
  参考文献：
  名称：

  Synthesis of (±)-Lotthanongine, a Novel Natural Product with a Flavan-Indole Hybrid Structure

  摘要：

  首次完成了具有黄烷-吲哚复合结构的天然产物洛坦农(3)的全合成，这一过程是通过路易斯酸催化的儿茶素和吲哚单元之间的C-C键形成实现的。

  DOI：

  10.1055/s-2005-868485

文献信息

• Synthesis of (±)-Lotthanongine, a Novel Natural Product with a Flavan-Indole Hybrid Structure
  作者：Keisuke Suzuki、Keisuke Hatakeyama、Ken Ohmori

  DOI：10.1055/s-2005-868485

  日期：——

  First total synthesis of lotthanongine (3), a natural product with a flavan-indole composite structure, has been achieved via the Lewis acid-catalyzed C-C bond formation between the catechin and the indole units.

  首次完成了具有黄烷-吲哚复合结构的天然产物洛坦农(3)的全合成，这一过程是通过路易斯酸催化的儿茶素和吲哚单元之间的C-C键形成实现的。
• NOVEL ANALOGUES OF EPICATECHIN AND RELATED POLYPHENOLS
  申请人：Sphaera Pharma Pvt. Ltd.

  公开号：EP2981260B1

  公开（公告）日：2021-01-13
• A structure-activity study for the inhibition of metalloproteinase-9 activity and gene expression by analogues of gallocatechin-3-gallate
  作者：M. Dell’Agli、S. Bellosta、L. Rizzi、G. V. Galli、M. Canavesi、F. Rota、R. Parente、E. Bosisio、S. Romeo

  DOI：10.1007/s00018-005-5422-7

  日期：2005.12

  Catechins are able to modulate the gelatinolytic activity of matrix metalloproteinase-9 (MMP-9) by reducing its release from macrophages. Gallocatechins decrease MMP-9 secretion by lowering MMP-9 promoter activity and mRNA levels. The effect appears to be dependent on some structural and stereochemical requirements. In this study, the relationship between chemical structure and activity was studied by testing the effect of analogues of (+/-)-gallocatechin-3-gallate (+/-)-GCG, selectively deprived of hydroxyl groups, on MMP-9 activity, transcription, and secretion. Our results indicate that (+/-)-GCG and (+/-)-catechin-3-gallate are characterized by a substitution pattern compatible with direct inhibition of MMP-9 activity. Conversely, when transcription was the target, (+/-)-trans-3-flavanol-3-benzoate, lacking all the hydroxyl groups, was the most effective both in lowering MMP-9 promoter activity and consequently protein secretion, and in inhibiting nuclear-factor-kappa B-driven transcription. Our results suggest that the structural requirements for enzyme inhibition are different from those necessary for targeting gene expression.