2-hydroxyimino-19β,28-epoxy-18α-olean-3-one | 1118559-84-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 2-hydroxyimino-19β,28-epoxy-18α-olean-3-one
• CAS: 1118559-84-4
• 化学式: C₃₀H₄₇NO₃
• 分子量: 469.708
• InChiKey: IHBJLYLXCRRMME-KCBLQPAFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.89
• 重原子数：
  34.0
• 可旋转键数：
  0.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  58.89
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-hydroxyimino-19β,28-epoxy-18α-olean-3-one 在 吡啶 、 chromium(III) oxide 、 sodium tetrahydroborate 、 硫酸 、 potassium carbonate 、 对甲苯磺酰氯 作用下， 以 甲醇 、 丙酮 为溶剂， 生成 2,3-Seco-19β,28-epoxy-18αH-oleanan-nitril-(2)-saeure-(3)-methylester
  参考文献：
  名称：

  The immunotropic activity of lupane and oleanane 2,3-seco-triterpenoids

  摘要：

  The immunotropic effect of the 2,3-seco derivatives of allobetulon, betulonic acid, and the methyl ester of betulonic acid were studied. It was found that the highest activity is shown by compounds with an oleanane fragment. The presence of a free C28-carboxyl group enhances the activity of lupane 2,3-seco derivatives. A significant contribution to the development of the immune response is introduced by a functional group at the C3 atom in the A ring-the C3-carboxy derivatives intensify the processes of antibody production and alter the number and ratio of leukocyte forms. It is shown that 2,3-seco-1-cyano-19 beta,28-epoxy-18 alpha-olean-3-oic acid stimulates humoral immunity with a positive influence on hematopoiesis.

  DOI：

  10.1134/s1068162010020147
• 作为产物：
  描述：

  allobetulone 在 potassium tert-butylate 、 亚硝酸异戊酯 作用下， 以 叔丁醇 为溶剂， 反应 0.5h， 以80%的产率得到2-hydroxyimino-19β,28-epoxy-18α-olean-3-one
  参考文献：
  名称：

  Synthesis of lupane and 19β,28-epoxy-18α-oleanane 2,3-seco-derivatives based on betulin

  摘要：

  合成了甲基白桦酸酯和异白桦酮的α-羟基肟。对它们进行贝克曼裂解反应，产生了萊潞烯和19β,28-环氧-18α-橄榄烯2,3-酮衍生物。

  DOI：

  10.1007/s10600-008-9135-7

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.