(-)-13,14-dihydroxy-8,11,13-podocarpatrien-7-one

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (-)-13,14-dihydroxy-8,11,13-podocarpatrien-7-one
• 英文别名: (4aS,10aS)-7,8-dihydroxy-1,1,4a-trimethyl-3,4,10,10a-tetrahydro-2H-phenanthren-9-one
• 化学式: C₁₇H₂₂O₃
• 分子量: 274.36
• InChiKey: LTZAECKOXUCKGJ-SUMWQHHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  Δ⁸⁽¹⁴⁾-podocarpen-13-one 在 甲醇 、 sodium tetrahydroborate 、 sodium acetate 、 2-碘酰基苯甲酸 作用下， 以 甲醇 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 19.0h， 生成 (-)-13,14-dihydroxy-8,11,13-podocarpatrien-7-one
  参考文献：
  名称：

  Synthesis and biological evaluation of ( − )-13,14-dihydroxy-8,11,13-podocarpatrien-7-one and derivatives from (+)-manool

  摘要：

  13,14-Dihydroxy-8,11,13-podocarpatrien-7-one (1) and a series of ring C aromatic diterpene derivatives were synthesised from (+)-manool (4) and evaluated for their cytotoxic, leishmanicidal and trypanocidal activities. Our results indicated that compound 1 and other podocarpane-type intermediates are cytotoxic. Cleavage of C6-C7 bond of compound 7 improved cytotoxic activity, indicating that, in particular, the 6,7-seco-podocarpane-type compound 20 might serve as a lead compound for further development.

  DOI：

  10.1080/14786419.2014.942299

文献信息

• Synthesis and biological evaluation of ( − )-13,14-dihydroxy-8,11,13-podocarpatrien-7-one and derivatives from (+)-manool
  作者：María L. Novoa、Yelisbeth Escalante、Liliana Maldonado、Iván Galindo-Castro、Annamil Álvarez、Katherine Figarella、Sabrina Marsiccobetre、Irina Arocha、Jais Nieves、Franklin Salazar、Carlos Gámez、Nieves Canudas、Eleonora Tropper、Teresa González、José E. Villamizar

  DOI：10.1080/14786419.2014.942299

  日期：2015.2.1

  13,14-Dihydroxy-8,11,13-podocarpatrien-7-one (1) and a series of ring C aromatic diterpene derivatives were synthesised from (+)-manool (4) and evaluated for their cytotoxic, leishmanicidal and trypanocidal activities. Our results indicated that compound 1 and other podocarpane-type intermediates are cytotoxic. Cleavage of C6-C7 bond of compound 7 improved cytotoxic activity, indicating that, in particular, the 6,7-seco-podocarpane-type compound 20 might serve as a lead compound for further development.