11,30-dioxo-30-methoxy-1-cyano-2,3-seco-2-norolean-12(13)-en-3-al | 1322687-23-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 11,30-dioxo-30-methoxy-1-cyano-2,3-seco-2-norolean-12(13)-en-3-al
• 英文别名: methyl (3S,4aR,6aR,7S,8R,10aR,10bS,12aS)-7-(cyanomethyl)-3,7,10a,10b,12a-pentamethyl-8-(2-methyl-1-oxopropan-2-yl)-6-oxo-1,2,4,4a,6a,8,9,10,11,12-decahydrochrysene-3-carboxylate
• CAS: 1322687-23-9
• 化学式: C₃₁H₄₅NO₄
• 分子量: 495.703
• InChiKey: MPQKRYUTPLNGEW-HTHQHRERSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  36
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  84.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  11,30-dioxo-30-methoxy-1-cyano-2,3-seco-2-norolean-12(13)-en-3-al 在 吡啶 、 盐酸羟胺 作用下， 以 乙醇 为溶剂， 以56%的产率得到methyl 3-hydroxyimino-1-cyano-11-oxo-2,3-seco-2-nor-18βH-olean-12(13)-ene-30-oate
  参考文献：
  名称：

  Functionalization, cyclization and antiviral activity of A-secotriterpenoids

  摘要：

  Triterpene derivatives with an α,β-alkenenitrile moiety in the five-membered ring A have been synthesized by nitrile anion cyclizations of 1-cyano-2,3-secotriterpenoids. Oxime-containing precursors, 2,3-secointermediates and five-membered ring A products of cyclizations were screened for in vitro antiviral activity against enveloped viruses - influenza A virus and human immunodeficiency virus type I (HIV-1). Lupane ketoxime and the 2,3-secolupane C-3 aldoxime which possess antiviral activities against both influenza A virus (EC50 12.9-18.2 μM) and HIV-1 (EC50 0.06 μM) were the most promising compounds.

  DOI：

  10.1016/j.ejmech.2013.12.058
• 作为产物：
  描述：

  2-hydroxyimino-11,30-dioxo-30-methoxyolean-12(13)-ene 在 吡啶 、 sodium tetrahydroborate 、 对甲苯磺酰氯 作用下， 以 甲醇 为溶剂， 反应 0.75h， 生成 11,30-dioxo-30-methoxy-1-cyano-2,3-seco-2-norolean-12(13)-en-3-al
  参考文献：
  名称：

  Synthesis of 1-cyano-2,3-seco-derivatives of glycyrrhetic acid

  摘要：

  以甘草亭酸为原料合成了 18βH-oleanane 系列的 1-氰基-2,3-seco-衍生物。

  DOI：

  10.1007/s10600-011-9893-5

文献信息

• Synthesis of 1-cyano-2,3-seco-derivatives of glycyrrhetic acid
  作者：I. A. Tolmacheva、N. V. Galaiko、V. V. Grishko

  DOI：10.1007/s10600-011-9893-5

  日期：2011.5

  1-Cyano-2,3-seco-derivatives of the 18βH-oleanane series were synthesized from glycyrrhetic acid.

  以甘草亭酸为原料合成了 18βH-oleanane 系列的 1-氰基-2,3-seco-衍生物。
• Functionalization, cyclization and antiviral activity of A-secotriterpenoids
  作者：Victoria V. Grishko、Natalia V. Galaiko、Irina A. Tolmacheva、Igor I. Kucherov、Vladimir F. Eremin、Eugene I. Boreko、Olga V. Savinova、Pavel A. Slepukhin

  DOI：10.1016/j.ejmech.2013.12.058

  日期：2014.8

  Triterpene derivatives with an α,β-alkenenitrile moiety in the five-membered ring A have been synthesized by nitrile anion cyclizations of 1-cyano-2,3-secotriterpenoids. Oxime-containing precursors, 2,3-secointermediates and five-membered ring A products of cyclizations were screened for in vitro antiviral activity against enveloped viruses - influenza A virus and human immunodeficiency virus type I (HIV-1). Lupane ketoxime and the 2,3-secolupane C-3 aldoxime which possess antiviral activities against both influenza A virus (EC50 12.9-18.2 μM) and HIV-1 (EC50 0.06 μM) were the most promising compounds.