5-heptadecatri-8(Z),11(Z),14(Z)-enylresorcinol | 83173-23-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 5-heptadecatri-8(Z),11(Z),14(Z)-enylresorcinol
• 英文别名: 5-(8′Z,11′Z,14′Z-heptadecatrienyl)resorcinol；1,3-Benzenediol, 5-(8,11,14-heptadecatrienyl)-, (Z,Z,Z)-；5-[(8Z,11Z,14Z)-heptadeca-8,11,14-trienyl]benzene-1,3-diol
• CAS: 83173-23-3
• 化学式: C₂₃H₃₄O₂
• 分子量: 342.522
• InChiKey: YPIUYRIMBUVEFO-PDBXOOCHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  25
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 5-heptadecatri-8(Z),11(Z),14(Z)-enylresorcinol 在 吡啶 作用下， 以9.0 mg的产率得到[3-acetyloxy-5-[(8Z,11Z,14Z)-heptadeca-8,11,14-trienyl]phenyl] acetate
  参考文献：
  名称：

  Hydroxyalkenylresorcinols from Stylogyne turbacensis

  摘要：

  Two new compounds, 5-(11'(S)-hydroxy-8'-heptadecenyl)resorcinol (3) and 5-(12'(S)-hydroxy-8',14'-heptadecadienyl)resorcinol (4), were isolated from the leaves of Stylogyne turbacensis together with the known analogue metabolites 1 and 2. Compounds 3 and 4 showed the strongest activity in the leishmania assay, 7 and 3 mu M, respectively, while compounds 1, 2, and 4 showed moderate activity against a drug-resistant strain of Trypanosoma cruzi with IC50 values of 30, 25, and 22 mu M, respectively. Additional testing in MCF-7 and NCI-H460 was performed for compounds 3 and 4. The structures of compounds 1-4 were elucidated using NMR, MS, and other spectroscopic data. The absolute stereochemistry of compounds 3 and 4 was also investigated using the Mosher ester approach. Peracetylated derivatives of these four metabolites were produced and their activities determined in the Trypanosoma cruzi assay.

  DOI：

  10.1021/np070081d