15-ketoatractyligenin methyl ester | 43059-73-0

• 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: 15-ketoatractyligenin methyl ester
• 英文别名: 15-dihydroatractyligenin methyl ester；methyl (1R,4R,5R,7R,9R,10S,13R)-7-hydroxy-9-methyl-14-methylidene-15-oxotetracyclo[11.2.1.01,10.04,9]hexadecane-5-carboxylate
• CAS: 43059-73-0
• 化学式: C₂₀H₂₈O₄
• 分子量: 332.44
• InChiKey: OLEMTCVBUUZJJE-CPSQXQKYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  15-ketoatractyligenin methyl ester 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 生成
  参考文献：
  名称：

  Piozzi,F. et al., Gazzetta Chimica Italiana, 1973, vol. 103, p. 211 - 217

  摘要：

  DOI：
• 作为产物：
  描述：

  atractyligenin 在 manganese(IV) oxide 作用下， 以 四氢呋喃 为溶剂， 反应 0.05h， 生成 15-ketoatractyligenin methyl ester
  参考文献：
  名称：

  Cytotoxic Activity of Some Natural and Synthetic ent-Kauranes

  摘要：

  Atractyligenin (1) and several synthetic derivatives were tested and found to be active against tumor cell replication. Compound 1 was readily converted to the 2,15-diketo (3) or 15-keto (4) derivatives, which contain an alpha,beta-unsaturated ketone. Compounds 3 and 4 showed significant cytotoxic activity against all six tested cancer cell lines and were most potent against 1A9 ovarian cancer cells with EC50 values of 0.2 and 0.3 mu M, respectively. These two 1-analogues are promising lead compounds for further investigation.

  DOI：

  10.1021/np060504w

文献信息

• Cytotoxic activity of several ent-kaurane derivatives of atractyligenin. Synthesis of unreported diterpenic skeleton by chemical rearrangement
  作者：Natale Badalamenti、Alessandro Vaglica、Antonella Maggio、Maurizio Bruno、Luana Quassinti、Massimo Bramucci、Filippo Maggi

  DOI：10.1016/j.phytochem.2022.113435

  日期：2022.12

  active with IC50 values of 0.427 and 0.723 μM against A375 melanoma cell line. Excellent results were also obtained against the colon cancer cell line CaCo2, with slightly lower antiproliferative activity. An interesting extension of the study should be to analyze the atractyligenin derivatives also as target for human melanoma and human colon cancer cells.

  对白术苷、羧义白菜苷、它们的苷分配白术绿素和几种合成衍生物进行了测试，发现对一组人类肿瘤细胞系具有活性。白术木红素经氧化、溴化和消除反应，得到几种化合物。通过从 3β-溴-2,15-二酮苍术木质素甲酯开始的化学重排合成单一骨架。合成的化合物对所有测试的细胞系均具有活性。特别是，15-酮苍术木根素甲酯和 3β-溴-2,15-二酮苍术木根素甲酯对 A375 黑色素瘤细胞系的 IC50 值为 0.427 和 0.723 μM。对结肠癌细胞系 CaCo2 也获得了极好的结果，抗增殖活性略低。该研究的一个有趣的扩展应该是分析白术木素衍生物也作为人类黑色素瘤和人类结肠癌细胞的靶标。
• Structural Characterization and Antimicrobial Evaluation of Atractyloside, Atractyligenin, and 15-Didehydroatractyligenin Methyl Ester
  作者：Federico Brucoli、Maria T. Borrello、Paul Stapleton、Gary N. Parkinson、Simon Gibbons

  DOI：10.1021/np300080w

  日期：2012.6.22

  We report the first complete structure elucidation of the ent-kaurane diterpenoid glycoside atractyloside (1) by means of NMR and X-ray diffractometry techniques. Extensive one- and two-dimensional NMR experiments were employed to assign the proton and carbon signals of 1, and crystallography experiments established the configurations of all stereogenic centers. Furthermore, we present a novel semisynthetic route for the preparation of the highly cytotoxic aglycone derivative of 1, 15-didehydroatractyligenin methyl ester (3). All compounds were tested for their antibiotic activity against Enterococcus faecalis, Escherichia coli, and several strains of Staphylococcus aureus, including fluoroquinolone-resistant (SA1199B) and two epidemic MRSA (EMRSA-15 and -16) strains. Compound 3 exhibited moderate activity against all of the Staph. aureus strains with an MIC value of 128 mg/L.