4-Hydroxy-3,3',4'-trimethoxy-stilben | 14207-97-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 4-Hydroxy-3,3',4'-trimethoxy-stilben
• 英文别名: 4-Hydroxy-3,3',4'-trimethoxy-stilbene；4-[2-(3,4-dimethoxyphenyl)ethenyl]-2-methoxyphenol
• CAS: 14207-97-7
• 化学式: C₁₇H₁₈O₄
• 分子量: 286.328
• InChiKey: JQBGNXRNJADPKG-UHFFFAOYSA-N

物化性质

• 熔点：
  178 °C
• 沸点：
  439.1±40.0 °C(Predicted)
• 密度：
  1.177±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 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-Hydroxy-3,3',4'-trimethoxy-stilben 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 生成 4-hydroxy-3,3',4'-trimethoxy-1,2-diphenylethane
  参考文献：
  名称：

  Design, synthesis and antitumour and anti-angiogenesis evaluation of 22 moscatilin derivatives

  摘要：

  Two series of moscatilin derivatives were designed, synthesized and evaluated as anti-tumor and anti-angiogenesis agents. Most of these compounds showed moderate-to-obvious cytotoxicity against five cancer cell lines (A549, HepG2, MDA-MB-231, MKN-45, HCT116). Among these cell lines, compounds had obvious effects on HCT116. Especially for 8Ae, the IC50 was low to 0.25 mu M. 8Ae can inhibit the viability and induce the apoptosis of HCT116 cells but exhibit no cytotoxic activity in noncancerous NCM460 colon cells. 8Ae can also arrest the G2/M cell cycle in HCT116 cells by inhibiting the alpha-tubulin expression. Zebrafish bioassay-guided screen showed the 22 moscatilin derivatives had potent anti-angiogenic activities and compound 8Ae had better activities than positive compound. Molecular docking indicated 8Ae interacted with tubulin at the affinity of -7.2 Kcal/mol. In conclusion, compound 8Ae was a potential antitumor and anti-angiogenesis candidate for further development.

  DOI：

  10.1016/j.bmc.2019.04.027
• 作为产物：
  描述：

  3,4-二甲氧基苄氯 在 sodium hydride 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 6.0h， 生成 4-Hydroxy-3,3',4'-trimethoxy-stilben
  参考文献：
  名称：

  Design, synthesis and antitumour and anti-angiogenesis evaluation of 22 moscatilin derivatives

  摘要：

  Two series of moscatilin derivatives were designed, synthesized and evaluated as anti-tumor and anti-angiogenesis agents. Most of these compounds showed moderate-to-obvious cytotoxicity against five cancer cell lines (A549, HepG2, MDA-MB-231, MKN-45, HCT116). Among these cell lines, compounds had obvious effects on HCT116. Especially for 8Ae, the IC50 was low to 0.25 mu M. 8Ae can inhibit the viability and induce the apoptosis of HCT116 cells but exhibit no cytotoxic activity in noncancerous NCM460 colon cells. 8Ae can also arrest the G2/M cell cycle in HCT116 cells by inhibiting the alpha-tubulin expression. Zebrafish bioassay-guided screen showed the 22 moscatilin derivatives had potent anti-angiogenic activities and compound 8Ae had better activities than positive compound. Molecular docking indicated 8Ae interacted with tubulin at the affinity of -7.2 Kcal/mol. In conclusion, compound 8Ae was a potential antitumor and anti-angiogenesis candidate for further development.

  DOI：

  10.1016/j.bmc.2019.04.027

文献信息

• Kurzin; Platonov; Evstigneev, Russian Journal of General Chemistry, 1997, vol. 67, # 9, p. 1475 - 1477
  作者：Kurzin、Platonov、Evstigneev、Maiorova

  DOI：——

  日期：——
• [EN] POLYHYDROXYLATED (1-PHENYL-2-PHENYL) ETHYLENE DERIVATIVES AS AN ANTI-AGEING AND PHOTOPROTECTIVE AGENT<br/>[FR] DÉRIVÉS DE (1-PHÉNYL-2-PHÉNYL)ÉTHYLÈNE POLYHYDROXYLÉ EN TANT QU'AGENT ANTIVIEILLISSEMENT ET PHOTOPROTECTEUR
  申请人：OREAL

  公开号：WO2016189153A9

  公开（公告）日：2017-03-23
• Design, synthesis and antitumour and anti-angiogenesis evaluation of 22 moscatilin derivatives
  作者：Li Guan、Junting Zhou、Qinghua Lin、Huilin Zhu、Wenyuan Liu、Baolin Liu、Yanbo Zhang、Jie Zhang、Jing Gao、Feng Feng、Wei Qu

  DOI：10.1016/j.bmc.2019.04.027

  日期：2019.6

  Two series of moscatilin derivatives were designed, synthesized and evaluated as anti-tumor and anti-angiogenesis agents. Most of these compounds showed moderate-to-obvious cytotoxicity against five cancer cell lines (A549, HepG2, MDA-MB-231, MKN-45, HCT116). Among these cell lines, compounds had obvious effects on HCT116. Especially for 8Ae, the IC50 was low to 0.25 mu M. 8Ae can inhibit the viability and induce the apoptosis of HCT116 cells but exhibit no cytotoxic activity in noncancerous NCM460 colon cells. 8Ae can also arrest the G2/M cell cycle in HCT116 cells by inhibiting the alpha-tubulin expression. Zebrafish bioassay-guided screen showed the 22 moscatilin derivatives had potent anti-angiogenic activities and compound 8Ae had better activities than positive compound. Molecular docking indicated 8Ae interacted with tubulin at the affinity of -7.2 Kcal/mol. In conclusion, compound 8Ae was a potential antitumor and anti-angiogenesis candidate for further development.