deoxyvsicinone A | 133566-77-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: deoxyvsicinone A
• 英文别名: Methyl 9-oxo-1,2,3,3a-tetrahydropyrrolo[2,1-b]quinazoline-4-carboxylate
• CAS: 133566-77-5
• 化学式: C₁₃H₁₄N₂O₃
• 分子量: 246.266
• InChiKey: SCHIRSCSWMOFGE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  49.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  deoxyvsicinone A 在 Daicel Chiralpak IC column 作用下， 以 正己烷 、 异丙醇 为溶剂， 生成 (+)-(3aR)-deoxyvsicinone A 、 (−)-(3aS)-deoxyvsicinone A
  参考文献：
  名称：

  Four pairs of alkaloid enantiomers from Isatis indigotica Fortune Ex Land with neuroprotective effects against H2O2-induced SH-SY5Y cell injury

  摘要：

  In the current study, four pairs of new enantiomeric alkaloids (1a/1b-4a/4b) were obtained from the leaves of Isatis indigotica Fortune Ex Land. Their structures were elucidated through spectroscopic methods and quantum mechanical calculations. Biologically, all isolates were evaluated for their neuroprotective effects against H2O2-induced SH-SY5Y cell injury. As a result, 1a and 1b exhibited enantioselective neuroprotective effects, further Annexin V-FITC/PI analysis showed that apoptosis ratios of 1a and 1b were reduced to 20.93% and 17.87%, respectively.

  DOI：

  10.1016/j.bioorg.2020.103650
• 作为产物：
  描述：

  脱氧鸭嘴花碱酮 在 sodium tetrahydroborate 、 三乙胺 作用下， 以 乙醇 、 苯 为溶剂， 生成 deoxyvsicinone A
  参考文献：
  名称：

  Synthesis, methylation, and acylation of 1,2-dihydrodeoxyvasicinones and their homologs

  摘要：

  DOI：

  10.1007/bf00601291

文献信息

• SHAXIDOYATOV, X. M.;BELOVA, G. A., XIMIYA PRIROD. SOED.,(1990) N, S. 659-663
  作者：SHAXIDOYATOV, X. M.、BELOVA, G. A.

  DOI：——

  日期：——
• Synthesis, methylation, and acylation of 1,2-dihydrodeoxyvasicinones and their homologs
  作者：Kh. M. Shakhidoyatov、G. A. Belova

  DOI：10.1007/bf00601291

  日期：1990.9
• Four pairs of alkaloid enantiomers from Isatis indigotica Fortune Ex Land with neuroprotective effects against H2O2-induced SH-SY5Y cell injury
  作者：Yu-Fei Xi、Li-Li Lou、Feng-Ying Han、Si-Fan Liu、Guo-Dong Yao、Bin Lin、Xiao-Xiao Huang、Xiao-Bo Wang、Shao-Jiang Song

  DOI：10.1016/j.bioorg.2020.103650

  日期：2020.3

  In the current study, four pairs of new enantiomeric alkaloids (1a/1b-4a/4b) were obtained from the leaves of Isatis indigotica Fortune Ex Land. Their structures were elucidated through spectroscopic methods and quantum mechanical calculations. Biologically, all isolates were evaluated for their neuroprotective effects against H2O2-induced SH-SY5Y cell injury. As a result, 1a and 1b exhibited enantioselective neuroprotective effects, further Annexin V-FITC/PI analysis showed that apoptosis ratios of 1a and 1b were reduced to 20.93% and 17.87%, respectively.