14,15-dinor-ent-halim-1(10)-ene-13,16-diol | 1567367-04-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 14,15-dinor-ent-halim-1(10)-ene-13,16-diol
• CAS: 1567367-04-7
• 化学式: C₁₈H₃₂O₂
• 分子量: 280.451
• InChiKey: LDNWFNMOXSHONY-WCGWOQOASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.92
• 重原子数：
  20.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  40.46
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  14,15-dinor-ent-halim-1(10)-ene-13,16-diol 在 氢碘酸 、 lead(IV) tetraacetate 、 溶剂黄146 作用下， 以 苯 为溶剂， 反应 5.33h， 生成 (2R,3R,17R)-2,3-dihydro-2,17-cyclo-aureanindol-15-ene
  参考文献：
  名称：

  Synthesis and biological activity of polyalthenol and pentacyclindole analogues

  摘要：

  A series of indole sesquiterpenes analogues of polyalthenol and pentacyclindole have been synthesized starting from ent-halimic acid in order to test their biological activity. These analogues include diverse oxidation levels at the sesquiterpenyl moiety and different functionalization on the indole ring. All synthetic derivatives were tested against a representative panel of Gram positive and Gram negative bacterial strains, and the human solid tumour cell lines A549 (non-small cell lung), HBL-100 (breast), HeLa (cervix), SW1573 (non-small cell lung), T-47D (breast) and WiDr (colon). Overall, the compounds presented activity against the cancer cell lines. The resulting lead, displaying a polyalthenol scaffold, showed GI50 values in the range 1.2-5.7 1.1M against all cell lines tested. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.12.012
• 作为产物：
  描述：

  16-hydroxy-14,15-dinor-ent-halima-1(10)-en-13-one 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 1.5h， 以97%的产率得到14,15-dinor-ent-halim-1(10)-ene-13,16-diol
  参考文献：
  名称：

  Synthesis and biological activity of polyalthenol and pentacyclindole analogues

  摘要：

  A series of indole sesquiterpenes analogues of polyalthenol and pentacyclindole have been synthesized starting from ent-halimic acid in order to test their biological activity. These analogues include diverse oxidation levels at the sesquiterpenyl moiety and different functionalization on the indole ring. All synthetic derivatives were tested against a representative panel of Gram positive and Gram negative bacterial strains, and the human solid tumour cell lines A549 (non-small cell lung), HBL-100 (breast), HeLa (cervix), SW1573 (non-small cell lung), T-47D (breast) and WiDr (colon). Overall, the compounds presented activity against the cancer cell lines. The resulting lead, displaying a polyalthenol scaffold, showed GI50 values in the range 1.2-5.7 1.1M against all cell lines tested. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.12.012