ent-14α-O-(p-fluorobenzoyl)-1,7-epoxy-6,7,15-trioxo-6,20-epoxy-6,7-seco-16-kaurene | 1353741-71-5

• 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: ent-14α-O-(p-fluorobenzoyl)-1,7-epoxy-6,7,15-trioxo-6,20-epoxy-6,7-seco-16-kaurene
• 英文别名: ent-(14α-O-p-flurobenzoyl)-1,7-epoxy-6,7,15-trioxo-6,20-epoxy-6,7-seco-16-kaurene；[(1R,4S,8R,12S,13S,16S,19R)-7,7-dimethyl-17-methylidene-2,9,18-trioxo-3,10-dioxapentacyclo[14.2.1.01,13.04,12.08,12]nonadecan-19-yl] 4-fluorobenzoate
• CAS: 1353741-71-5
• 化学式: C₂₇H₂₇FO₇
• 分子量: 482.506
• InChiKey: FLQITQFDGPUILE-LJSMDWFQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  35
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  96
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  冬凌草甲素 在 sodium periodate 、 Jones reagent 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 水 、 丙酮 为溶剂， 反应 24.25h， 生成 ent-14α-O-(p-fluorobenzoyl)-1,7-epoxy-6,7,15-trioxo-6,20-epoxy-6,7-seco-16-kaurene
  参考文献：
  名称：

  Synthesis and antimycobacterial evaluation of natural oridonin and its enmein-type derivatives

  摘要：

  A series of enmein-type derivatives were synthesized and assayed for their antimycobacterial effects. The structures of the synthesized compounds were established by H-1 NMR, C-13 NMR and mass spectral analysis. All the compounds were screened for their antimycobacterial properties against Mycobacterium phlei, Mycobacterium smegmatis and Mycobacterium marinum. Compounds 2, 6g and 6i were found to exhibit potent antimycobacterial activity against M. phlei at a concentration of 0.5 mu g/mL, which was comparable to that of positive drug streptomycin. Furthermore, five compounds were tested against Mycobacterium tuberculosis H(37)Rv based on the promising preliminary screening results. Among them, compound 10 showed potent activity with IC50 value of I 7.1 mu g/mL against M. tuberculosis H37Rv strain. Thus, compound 10 could emerge as a promising lead for further research work. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.fitote.2014.10.005

文献信息

• Library Construction and Biological Evaluation of Enmein-Type Diterpenoid Analogues as Potential Anticancer Agents
  作者：Dahong Li、Shengtao Xu、Hao Cai、Lingling Pei、Lei Wang、Xiaoming Wu、Hequan Yao、Jieyun Jiang、Yijun Sun、Jinyi Xu

  DOI：10.1002/cmdc.201200559

  日期：2013.5

  A library of promising enmein‐type 14‐O‐diterpenoid derivatives was constructed from a commercially available kaurene‐type oridonin by practical and efficient synthetic methods. These synthetic derivatives were evaluated for their antiproliferative activities against a set of four human cancer cell lines. The IC50 values are similar to or improved over those of the parent molecule and paclitaxel, the

  通过实用有效的合成方法，从市售的kaurene型oridonin中构建了有前途的enmein型14- O-二萜衍生物衍生物库。对这些合成衍生物针对一组四种人类癌细胞系的抗增殖活性进行了评估。IC 50值类似于或优于母体分子和紫杉醇，后者被用作阳性对照。进一步研究了化合物29对人肝癌Bel‐7402细胞的凋亡特性，以更好地了解其作用方式。此外，化合物29在胃癌的鼠模型（MGC-803小鼠）的研究中，MHC被证明在体内具有有效的抗肿瘤活性。这些结果值得对这些基于二萜的类似物作为潜在的新型抗癌化学疗法进行进一步的临床前研究。
• 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.
• Synthesis and antimycobacterial evaluation of natural oridonin and its enmein-type derivatives
  作者：Shengtao Xu、Lingling Pei、Dahong Li、Hong Yao、Hao Cai、Hequan Yao、Xiaoming Wu、Jinyi Xu

  DOI：10.1016/j.fitote.2014.10.005

  日期：2014.12

  A series of enmein-type derivatives were synthesized and assayed for their antimycobacterial effects. The structures of the synthesized compounds were established by H-1 NMR, C-13 NMR and mass spectral analysis. All the compounds were screened for their antimycobacterial properties against Mycobacterium phlei, Mycobacterium smegmatis and Mycobacterium marinum. Compounds 2, 6g and 6i were found to exhibit potent antimycobacterial activity against M. phlei at a concentration of 0.5 mu g/mL, which was comparable to that of positive drug streptomycin. Furthermore, five compounds were tested against Mycobacterium tuberculosis H(37)Rv based on the promising preliminary screening results. Among them, compound 10 showed potent activity with IC50 value of I 7.1 mu g/mL against M. tuberculosis H37Rv strain. Thus, compound 10 could emerge as a promising lead for further research work. (C) 2014 Elsevier B.V. All rights reserved.