[(1R,4S,8R,9R,12S,13S,16S,19R)-9-hydroxy-7,7-dimethyl-17-methylidene-2,18-dioxo-3,10-dioxapentacyclo[14.2.1.01,13.04,12.08,12]nonadecan-19-yl] acetate | 16763-53-4

• 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: [(1R,4S,8R,9R,12S,13S,16S,19R)-9-hydroxy-7,7-dimethyl-17-methylidene-2,18-dioxo-3,10-dioxapentacyclo[14.2.1.01,13.04,12.08,12]nonadecan-19-yl] acetate
• CAS: 16763-53-4
• 化学式: C₂₂H₂₈O₇
• 分子量: 404.46
• InChiKey: GBWSOZILVHIOTA-HUAGGLHYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  29
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  99.1
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  oridonin 在 4-二甲氨基吡啶 、 sodium periodate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 、 水 为溶剂， 生成 [(1R,4S,8R,9R,12S,13S,16S,19R)-9-hydroxy-7,7-dimethyl-17-methylidene-2,18-dioxo-3,10-dioxapentacyclo[14.2.1.01,13.04,12.08,12]nonadecan-19-yl] acetate
  参考文献：
  名称：

  Design, synthesis and antimycobacterial activity evaluation of natural oridonin derivatives

  摘要：

  In an effort to develop novel potent antitubercular drugs, thirty-one oridonin derivatives were designed and prepared. All the compounds obtained were screened for their in vitro activities against Mycobacterium phlei, Mycobacterium smegmatis and Mycobacterium marinum. Among them, thirteen compounds showed significant inhibitory activity against M. phlei with MICs less than 2 mu g/mL. Compounds 2k, 8d, 10c, 10d containing trans-cinnamic acid moiety were the most potent (MIC = 0.5 mu g/mL), comparable to the well-known antitubercular drug streptomycin. The preliminary structure-activity relationships (SARs) were also analyzed. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.04.119

文献信息

• Enmein-type diterpenoid analogs from natural kaurene-type oridonin: Synthesis and their antitumor biological evaluation
  作者：Dahong Li、Shengtao Xu、Hao Cai、Lingling Pei、Hengyuan Zhang、Lei Wang、Hequan Yao、Xiaoming Wu、Jieyun Jiang、Yijun Sun、Jinyi Xu

  DOI：10.1016/j.ejmech.2013.04.012

  日期：2013.6

  A series of enmein-type diterpenoid analogs (11–20) derived from natural kaurene-type diterpenoid oridonin were synthesized and biologically evaluated. All target compounds showed improved anti-proliferative activities against four human cancer cell lines compared with natural oridonin and parent compound 10. Some compounds were more potent than positive control Taxol. Furthermore, mechanistic investigation

  一系列enmein型的二萜类类似物（11 - 20）从天然贝壳杉烯型二萜衍生冬凌草甲素合成和生物学评价。与天然冬凌草甲素和母体化合物10相比，所有目标化合物均显示出针对四种人类癌细胞系的抗增殖活性提高。一些化合物比阳性对照紫杉醇更有效。此外，机理研究表明，代表性化合物17通过氧化应激触发的线粒体相关caspase依赖性途径，在人肝癌Bel-7402细胞中以低微摩尔水平影响细胞周期并诱导凋亡。
• Design, synthesis and antimycobacterial activity evaluation of natural oridonin derivatives
  作者：Shengtao Xu、Dahong Li、Lingling Pei、Hong Yao、Chengqian Wang、Hao Cai、Hequan Yao、Xiaoming Wu、Jinyi Xu

  DOI：10.1016/j.bmcl.2014.04.119

  日期：2014.7

  In an effort to develop novel potent antitubercular drugs, thirty-one oridonin derivatives were designed and prepared. All the compounds obtained were screened for their in vitro activities against Mycobacterium phlei, Mycobacterium smegmatis and Mycobacterium marinum. Among them, thirteen compounds showed significant inhibitory activity against M. phlei with MICs less than 2 mu g/mL. Compounds 2k, 8d, 10c, 10d containing trans-cinnamic acid moiety were the most potent (MIC = 0.5 mu g/mL), comparable to the well-known antitubercular drug streptomycin. The preliminary structure-activity relationships (SARs) were also analyzed. (C) 2014 Elsevier Ltd. All rights reserved.