methyl (4aR,4bR,7R,10aS)-7-ethenyl-4b-hydroxy-1,1,7-trimethyl-10-oxospiro[2,3,4,5,6,10a-hexahydrophenanthrene-9,2'-oxirane]-4a-carboxylate | 1351231-70-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子
• 英文名称: methyl (4aR,4bR,7R,10aS)-7-ethenyl-4b-hydroxy-1,1,7-trimethyl-10-oxospiro[2,3,4,5,6,10a-hexahydrophenanthrene-9,2'-oxirane]-4a-carboxylate
• CAS: 1351231-70-3
• 化学式: C₂₂H₃₀O₅
• 分子量: 374.477
• InChiKey: GKQYRCLWWVMCRU-SAFSJCAZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  76.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  重氮甲烷 、 sphaeropsidin A 以 甲醇 、 乙醚 为溶剂， 反应 24.0h， 以100 mg的产率得到8,14-methylenesphaeropsidin A methyl ester
  参考文献：
  名称：

  In Vitro Antibacterial Activity of Sphaeropsidins and Chemical Derivatives toward Xanthomonas oryzae pv. oryzae, the Causal Agent of Rice Bacterial Blight

  摘要：

  Sphaeropsidin A, the main phytotoxin produced by Diplodia cupressi, as well as the two natural analogues sphaeropsidins B and C and 14 derivatives obtained by chemical modifications were assayed for antibacterial activity against Xanthomonas oryzae pv. oryzae, Pseudomonas fuscovaginae, and Burkholderia glumae, the causal agents of severe bacterial rice diseases. The results showed a strong and specific activity of sphaeropsidin A against X. oryzae pv. oryzae, while no activity was observed against the other two pathogens. The results of structure-activity relationship studies showed that structural features important to impart this antibacterial activity are the presence of the C-7 carbonyl group and the hemiketalic lactone functionality. The C-13 vinyl group, the double bond of ring C, and/or the tertiary C-9 hydroxy group, as well as the pimarane arrangement of the tricylic carbon skeleton, were also important for the antibacterial activity. These findings may be useful in designing novel compounds for practical applications in agriculture.

  DOI：

  10.1021/np200625m