(R,E)-6-hydroxy-6-((2S,8S,9R,10R,13R,14S,16R,17R)-16-hydroxy-4,4,9,13,14-pentamethyl-3,11-dioxo-2-(tosyloxy)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-2-methyl-5-oxohept-3-en-2-yl acetate | 1374959-43-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: (R,E)-6-hydroxy-6-((2S,8S,9R,10R,13R,14S,16R,17R)-16-hydroxy-4,4,9,13,14-pentamethyl-3,11-dioxo-2-(tosyloxy)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-2-methyl-5-oxohept-3-en-2-yl acetate
• CAS: 1374959-43-9
• 化学式: C₃₉H₅₂O₁₀S
• 分子量: 712.902
• InChiKey: YGLXSUXYWZODON-KBIXXLEBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.22
• 重原子数：
  50.0
• 可旋转键数：
  8.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  161.34
• 氢给体数：
  2.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  (R,E)-6-hydroxy-6-((2S,8S,9R,10R,13R,14S,16R,17R)-16-hydroxy-4,4,9,13,14-pentamethyl-3,11-dioxo-2-(tosyloxy)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-2-methyl-5-oxohept-3-en-2-yl acetate 在 四丁基溴化铵 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 35.0h， 以86%的产率得到2-deoxy-2-bromo-cucurbitacin B
  参考文献：
  名称：

  二氢葫芦素B和葫芦素B衍生物的合成及细胞毒活性评价

  摘要：

  两种葫芦素（dihydrocucurbitacin B（1）和葫芦素B（2））可以分别作为原料从野勃氏菌（Wilbrandia ebracteata）的根和uff的丝瓜（Luffa operculata）的果实中大量获得，作为制备库的起始材料。 29种半合成衍生物。进行的结构变化包括环A和B以及侧链中官能团的去除，修饰或置换。所有新的半合成化合物以及1和2在体外测试了它们对非小细胞肺癌细胞（A549细胞）的细胞毒性作用。这些化合物中的一些显示出对A549肿瘤细胞有效的中等活性，尤其是在环A修饰的葫芦素B衍生物。

  DOI：

  10.1016/j.bmc.2012.03.001
• 作为产物：
  描述：

  葫芦素 B 、 对甲苯磺酰氯 在 三乙烯二胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以77%的产率得到(R,E)-6-hydroxy-6-((2S,8S,9R,10R,13R,14S,16R,17R)-16-hydroxy-4,4,9,13,14-pentamethyl-3,11-dioxo-2-(tosyloxy)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-2-methyl-5-oxohept-3-en-2-yl acetate
  参考文献：
  名称：

  二氢葫芦素B和葫芦素B衍生物的合成及细胞毒活性评价

  摘要：

  两种葫芦素（dihydrocucurbitacin B（1）和葫芦素B（2））可以分别作为原料从野勃氏菌（Wilbrandia ebracteata）的根和uff的丝瓜（Luffa operculata）的果实中大量获得，作为制备库的起始材料。 29种半合成衍生物。进行的结构变化包括环A和B以及侧链中官能团的去除，修饰或置换。所有新的半合成化合物以及1和2在体外测试了它们对非小细胞肺癌细胞（A549细胞）的细胞毒性作用。这些化合物中的一些显示出对A549肿瘤细胞有效的中等活性，尤其是在环A修饰的葫芦素B衍生物。

  DOI：

  10.1016/j.bmc.2012.03.001

文献信息

• Chemical Modification Produces Species-Specific Changes in Cucurbitacin Antifeedant Effect
  作者：Karen Luise Lang、Emilio Deagosto、Lara Almida Zimmermann、Vanessa Rocha Machado、Lílian Sibelle Campos Bernardes、Eloir Paulo Schenkel、Fernando Javier Duran、Jorge Palermo、Carmen Rossini

  DOI：10.1021/jf4002457

  日期：2013.6.12

  Cucurbitacins are secondary metabolites that mediate insect plant interactions not only as allomones against generalists but also as kairomones for specialist herbivores. This study was undertaken to identify the potential of cucurbitacin derivatives as insect antifeedant agents. The antifeedant capacity against a Cucurbitaceae specialist [Epilachna paenulata (Coleoptera: Coccinellidae)] and a polyphagous insect [Pseudaletia adultera (Lepidoptera: Noctuidae)] was evaluated in preference tests in which the insects were given a choice between food plants either treated with the cucurbitacin derivatives or treated with the solvent. The activity was found not to be related to the basic cucurbitacin skeleton, as only IS of the 28 tested cucurbitacin derivatives were active. Only one of the tested compounds was phagostimulant to the specialist insect (the hemissuccinate of 16-oxo-dihydrocucurbitacin B derivative), while all other active derivatives were deterrent against one of the insects (13 compounds) or both of them (3 compounds). Changes in ring A of the cucurbitacins, as well as in the side chain, modified the activity. As a general trend, when chemical modifications of the basic structure produced a change in activity, the response was opposite in both insects used as biodetectors, indicating that a selective variation in the activity may be achieved by chemical modifications of the cucurbitacin skeleton.