ent-6β-hydroxy-(14α-O-benzoyl)-1,7-epoxy-7,15-dioxo-6,20-hemiketal-6,7-seco-16-kaurene | 1445994-79-5

• 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-6β-hydroxy-(14α-O-benzoyl)-1,7-epoxy-7,15-dioxo-6,20-hemiketal-6,7-seco-16-kaurene
• 英文别名: [(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] benzoate
• CAS: 1445994-79-5
• 化学式: C₂₇H₃₀O₇
• 分子量: 466.531
• InChiKey: VNQNNBNCQOCSRP-SUVBAOSJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  34
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.59
• 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：

  冬凌草甲素 在 sodium periodate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 水 为溶剂， 反应 24.0h， 生成 ent-6β-hydroxy-(14α-O-benzoyl)-1,7-epoxy-7,15-dioxo-6,20-hemiketal-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

• 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。
• 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.