4'-Methoxyaucuparin | 54961-04-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4'-Methoxyaucuparin
• 英文别名: 4-Hydroxy-3,4',5-trimethoxybiphenyl；(1,1'-Biphenyl)-4-ol, 3,4',5-trimethoxy-；2,6-dimethoxy-4-(4-methoxyphenyl)phenol
• CAS: 54961-04-5
• 化学式: C₁₅H₁₆O₄
• 分子量: 260.29
• InChiKey: MKDRXVRMAGKWEO-UHFFFAOYSA-N

物化性质

• 沸点：
  384.7±42.0 °C(Predicted)
• 密度：
  1.156±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4'-Methoxyaucuparin 在 potassium fluoride 、 三溴化硼 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 20.17h， 生成 [1,1':4',1"-terphenyl]-2',3,4,4",6'-pentaol
  参考文献：
  名称：

  A novel p-terphenyl derivative inducing cell-cycle arrest and apoptosis in MDA-MB-435 cells through topoisomerase inhibition

  摘要：

  A novel series of p-terphenyl derivatives (1-4, 1a-4a) was successfully synthesized and their in vitro anticancer activities were evaluated. Compound 1, showing the best antiproliferative activity with IC50 < 1 mu M against MDA-MB-435 cells, was further investigated. Compound 1 brought about a remarkable accumulation of MDA-MB-435 cells in G2/M phase prior to the induction of apoptosis. Further antitumor mechanism study indicated that compound 1, which inhibited the enzyme activity of Topo I and Topo II alpha by interfering predominantly with the enzyme, could be topoisomerase suppressors instead of poisons. We conclude that compound 1 represents a novel class of Topo catalytic suppressors for developing new chemotherapeutic agents. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.07.020
• 作为产物：
  描述：

  2,6-二甲氧基苯酚 在 N-溴代丁二酰亚胺(NBS) 、 palladium 10% on activated carbon 、 sodium hydride 、 potassium hydroxide 作用下， 以 氯仿 、 mineral oil 为溶剂， 反应 2.0h， 生成 4'-Methoxyaucuparin
  参考文献：
  名称：

  Suzuki–Miyaura Coupling of Halophenols and Phenol Boronic Acids: Systematic Investigation of Positional Isomer Effects and Conclusions for the Synthesis of Phytoalexins from Pyrinae

  摘要：

  The Suzuki-Miyaura couplings of o-, m-, and p-halophenols with o-, m-, and p-phenol boronic acids were investigated for all combinations under standardized conditions, using Pd/C as a heterogeneous catalyst and water as a solvent. In the case of iodophenols, conventional heating was used, while for bromophenols significantly better results could be obtained using microwave irradiation. This systematic study revealed that 2,4'-biphenol is particularly difficult to access, irrespective of the starting materials used, but that these difficulties can be overcome by using different additives. The conclusions drawn from this investigation allowed us to identify conditions for the protecting group-free or minimized total synthesis of biaryl-type phytoalexins. These compounds possess antibacterial activity and are produced by fruit trees as a response to microbial infection.

  DOI：

  10.1021/jo500675a

文献信息

• Formation and exudation of biphenyl and dibenzofuran phytoalexins by roots of the apple rootstock M26 grown in apple replant disease soil
  作者：Belnaser A. Busnena、Till Beuerle、Felix Mahnkopp-Dirks、Traud Winkelmann、Ludger Beerhues、Benye Liu

  DOI：10.1016/j.phytochem.2021.112972

  日期：2021.12
• A novel p-terphenyl derivative inducing cell-cycle arrest and apoptosis in MDA-MB-435 cells through topoisomerase inhibition
  作者：Jin Qiu、Baobing Zhao、Yan Shen、Wang Chen、Yudao Ma、Yuemao Shen

  DOI：10.1016/j.ejmech.2013.07.020

  日期：2013.10

  A novel series of p-terphenyl derivatives (1-4, 1a-4a) was successfully synthesized and their in vitro anticancer activities were evaluated. Compound 1, showing the best antiproliferative activity with IC50 < 1 mu M against MDA-MB-435 cells, was further investigated. Compound 1 brought about a remarkable accumulation of MDA-MB-435 cells in G2/M phase prior to the induction of apoptosis. Further antitumor mechanism study indicated that compound 1, which inhibited the enzyme activity of Topo I and Topo II alpha by interfering predominantly with the enzyme, could be topoisomerase suppressors instead of poisons. We conclude that compound 1 represents a novel class of Topo catalytic suppressors for developing new chemotherapeutic agents. (C) 2013 Elsevier Masson SAS. All rights reserved.
• Suzuki–Miyaura Coupling of Halophenols and Phenol Boronic Acids: Systematic Investigation of Positional Isomer Effects and Conclusions for the Synthesis of Phytoalexins from Pyrinae
  作者：Bernd Schmidt、Martin Riemer

  DOI：10.1021/jo500675a

  日期：2014.5.2

  The Suzuki-Miyaura couplings of o-, m-, and p-halophenols with o-, m-, and p-phenol boronic acids were investigated for all combinations under standardized conditions, using Pd/C as a heterogeneous catalyst and water as a solvent. In the case of iodophenols, conventional heating was used, while for bromophenols significantly better results could be obtained using microwave irradiation. This systematic study revealed that 2,4'-biphenol is particularly difficult to access, irrespective of the starting materials used, but that these difficulties can be overcome by using different additives. The conclusions drawn from this investigation allowed us to identify conditions for the protecting group-free or minimized total synthesis of biaryl-type phytoalexins. These compounds possess antibacterial activity and are produced by fruit trees as a response to microbial infection.