1-cyano-19β,28-epoxy-2-nor-18αH-olean-1(3)-ene | 1474092-04-0

• 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: 1-cyano-19β,28-epoxy-2-nor-18αH-olean-1(3)-ene
• 英文别名: (1R,4R,5R,8S,12S,13S,16R,17R,18R)-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: 1474092-04-0
• 化学式: C₃₀H₄₅NO
• 分子量: 435.693
• InChiKey: UIOLRCWUGQAKSM-OQRSRIDPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.2
• 重原子数：
  32
• 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：
  33
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  allobetulone 在 吡啶 、 sodium tetrahydroborate 、 potassium tert-butylate 、 对甲苯磺酰氯 、 亚硝酸异戊酯 作用下， 以 甲醇 、 叔丁醇 为溶剂， 反应 1.58h， 生成 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

• Synthesis and Transformation of Triterpenoids with a β-Ketonitrile Fragment in Five-Membered Ring A
  作者：I. A. Tolmacheva、E. V. Igosheva、O. S. Eltsov、V. V. Grishko

  DOI：10.1007/s10600-020-03233-6

  日期：2020.11

  Triterpenoids with a β-ketonitrile group in five-membered ring A were synthesized via intramolecular oxonitrile cyclization of C-3 methyl esters of 1-cyano-substituted 2,3-seco-triterpene acids. The intramolecular cyclization to form the triterpene ketonitriles and subsequent reduction of the oxo groups to give C-1 and C-3 substituents in the β-orientation were confirmed to be stereoselective. Alkaline

  在五元环 A 中具有 β-酮腈基团的三萜类化合物是通过 1-氰基取代的 2,3-seco-三萜酸的 C-3 甲酯的分子内氧腈环化合成的。分子内环化形成三萜酮腈和随后的氧代基团还原以在 β 取向中产生 C-1 和 C-3 取代基被证实是立体选择性的。酮腈的碱水解还原氰基以形成相应的 3-oxo-2-nor-derivative，而 β-羟基腈的还原和酰化在三萜类五元环 A 中形成α,β-烯腈片段。
• 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.