3-amino-1-cyano-19β,28-epoxy-2-nor-18αH-olean-1(3)-ene | 1474092-09-5

• 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: 3-amino-1-cyano-19β,28-epoxy-2-nor-18αH-olean-1(3)-ene
• 英文别名: (1R,4R,5R,8R,12R,13S,16R,17R,18R)-10-amino-4,5,9,9,12,19,19-heptamethyl-23-oxahexacyclo[16.3.2.01,17.04,16.05,13.08,12]tricos-10-ene-11-carbonitrile
• CAS: 1474092-09-5
• 化学式: C₃₀H₄₆N₂O
• 分子量: 450.708
• InChiKey: UYBAXAIXLSPANV-LBZYMTBISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  33
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  59
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1,4-dicyano-19β,28-epoxy-2,3-seco-2-nor-18αH-oleanane 在 potassium tert-butylate 作用下， 以 叔丁醇 为溶剂， 反应 1.5h， 以19%的产率得到3-amino-1-cyano-19β,28-epoxy-2-nor-18αH-olean-1(3)-ene
  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

文献信息

• 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.