1,2-苯二醇,3-甲氧基-4-(3-苯基-2-丙烯基)-,(E)- | 101153-43-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 中文名称: 1,2-苯二醇,3-甲氧基-4-(3-苯基-2-丙烯基)-,(E)-
• 英文名称: hydroxyobtustyrene
• 英文别名: Hydroxyobustyrene；3-methoxy-4-[(E)-3-phenylprop-2-enyl]benzene-1,2-diol
• CAS: 101153-43-9
• 化学式: C₁₆H₁₆O₃
• 分子量: 256.301
• InChiKey: WGXMQVRYJCAUFL-VMPITWQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,2-苯二醇,3-甲氧基-4-(3-苯基-2-丙烯基)-,(E)- 、 1-溴-3-甲基-2-丁烯 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 1.0h， 以10.7 mg的产率得到3-methoxy-1,2-bis(3-methylbut-2-enoxy)-4-[(E)-3-phenylprop-2-enyl]benzene
  参考文献：
  名称：

  Synthetic cinnamylphenol derivatives as cancer chemopreventive agents

  摘要：

  Several substituted cinnamylphenol (1,3-diphenylpropene) derivatives were synthesized and tested for their inhibitory activities against in vitro Epstein-Barr virus early antigen activation induced by 12-O-tetradecanoylphorbol-13-acetate in Raji cells. The prenylated cinnamylphenols were found to show remarkably potent activity. Furthermore, prenylated cinnamylphenols (19 and 25) exhibited a marked inhibitory effect on mouse skin tumor promotion in an in vivo two-stage carcinogenesis test. These results indicate that some prenylated cinnamylphenols might be valuable as potential cancer chemopreventive agents (anti-tumor promoters). (c) 2007 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2006.12.024
• 作为产物：
  描述：

  3-甲氧基儿茶酚 、 3-苯基丙-2-烯-1-醇 在 甲酸 作用下， 以 水 为溶剂， 反应 0.5h， 以196 mg的产率得到3-Methoxy-6-((E)-3-phenyl-allyl)-benzene-1,2-diol
  参考文献：
  名称：

  Synthetic cinnamylphenol derivatives as cancer chemopreventive agents

  摘要：

  Several substituted cinnamylphenol (1,3-diphenylpropene) derivatives were synthesized and tested for their inhibitory activities against in vitro Epstein-Barr virus early antigen activation induced by 12-O-tetradecanoylphorbol-13-acetate in Raji cells. The prenylated cinnamylphenols were found to show remarkably potent activity. Furthermore, prenylated cinnamylphenols (19 and 25) exhibited a marked inhibitory effect on mouse skin tumor promotion in an in vivo two-stage carcinogenesis test. These results indicate that some prenylated cinnamylphenols might be valuable as potential cancer chemopreventive agents (anti-tumor promoters). (c) 2007 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2006.12.024

文献信息

• Inhibitors of Prostaglandin Biosynthesis from Dalbergia odorifera.
  作者：Yukihiro GODA、Fumiyuki KIUCHI、Masaaki SHIBUYA、Ushio SANKAWA

  DOI：10.1248/cpb.40.2452

  日期：——

  (+)-isoduartin (isoflavan), odoriflavene (isoflav-3-ene) and (-)-odoricarpan (pterocarpan) were isolated and their structures were elucidated on the basis of chemical and spectroscopic methods. Of the fifteen compounds isolated, cinnamylphenols, isoflavans, isoflavene and benzoic acid derivative significantly inhibited prostaglandin biosynthesis as well as platelet aggregation induced by arachidonic acid.

  Dalbergia odorifera T. Chen（Leguminosae）的根心材是一种用于停滞血液综合症（血液停滞；日语，oketsu）的中药（日语名称koshinko）。除10种已知化合物外，还分离了五种新的酚类化合物，异丁烯基苯乙烯和羟基邻苯二酚（肉桂基酚），（+）-异都丁（isoflavan），奥多弗拉芬（isoflav-3-ene）和（-）-奥多氯潘（罗汉果）。在化学和光谱学方法的基础上进行了阐明。在分离的15种化合物中，肉桂基酚，异黄烷酮，异黄酮和苯甲酸衍生物显着抑制前列腺素的生物合成以及花生四烯酸诱导的血小板凝集。
• Synthetic cinnamylphenol derivatives as cancer chemopreventive agents
  作者：Chihiro Ito、Masataka Itoigawa、Tetsufumi Kanematsu、Yuuki Imamura、Harukuni Tokuda、Hoyoku Nishino、Hiroshi Furukawa

  DOI：10.1016/j.ejmech.2006.12.024

  日期：2007.7

  Several substituted cinnamylphenol (1,3-diphenylpropene) derivatives were synthesized and tested for their inhibitory activities against in vitro Epstein-Barr virus early antigen activation induced by 12-O-tetradecanoylphorbol-13-acetate in Raji cells. The prenylated cinnamylphenols were found to show remarkably potent activity. Furthermore, prenylated cinnamylphenols (19 and 25) exhibited a marked inhibitory effect on mouse skin tumor promotion in an in vivo two-stage carcinogenesis test. These results indicate that some prenylated cinnamylphenols might be valuable as potential cancer chemopreventive agents (anti-tumor promoters). (c) 2007 Elsevier Masson SAS. All rights reserved.