2-hydroxyimino-3-oxolup-20(29)-en-28-oic acid | 1205673-82-0

• 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-3-oxolup-20(29)-en-28-oic acid
• CAS: 1205673-82-0
• 化学式: C₃₀H₄₅NO₄
• 分子量: 483.692
• InChiKey: DSRWVVPQDXKXCC-DICHFOODSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.74
• 重原子数：
  35.0
• 可旋转键数：
  2.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  86.96
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-hydroxyimino-3-oxolup-20(29)-en-28-oic acid 在 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  羽扇豆和α-癸烷烯丙酰胺的合成

  摘要：

  由桦木酸制备在环 A 中具有 α-酮肟和 α-羟基肟基团的 Lupane C-28 单烯丙酰胺。以 A-secolupane C-3(28) 单和二烯丙酰胺的形成为例，证明了通过草酰氯或草酰氯裂解桦木脑和桦木酸 α-肟，可以一步合成 2,3-次三萜酰胺。亚硫酰氯，随后由烯丙胺原位形成的 2,3-次氯三萜酸进行酰胺化。与之前描述的从桦木酸制备 A-secotriteperene 酰胺的五步方法相比，所提出的方法使 2,3-secolupane C-3,C-28 二酰胺的产率提高了五倍。

  DOI：

  10.1007/s10600-013-0582-4
• 作为产物：
  描述：

  路路通酸 在 potassium tert-butylate 、 亚硝酸异戊酯 作用下， 以 叔丁醇 为溶剂， 生成 2-hydroxyimino-3-oxolup-20(29)-en-28-oic acid
  参考文献：
  名称：

  羽扇豆和α-癸烷烯丙酰胺的合成

  摘要：

  由桦木酸制备在环 A 中具有 α-酮肟和 α-羟基肟基团的 Lupane C-28 单烯丙酰胺。以 A-secolupane C-3(28) 单和二烯丙酰胺的形成为例，证明了通过草酰氯或草酰氯裂解桦木脑和桦木酸 α-肟，可以一步合成 2,3-次三萜酰胺。亚硫酰氯，随后由烯丙胺原位形成的 2,3-次氯三萜酸进行酰胺化。与之前描述的从桦木酸制备 A-secotriteperene 酰胺的五步方法相比，所提出的方法使 2,3-secolupane C-3,C-28 二酰胺的产率提高了五倍。

  DOI：

  10.1007/s10600-013-0582-4

文献信息

• Synthesis and antiviralactivity of 2,3-seco-derivatives of betulonic acid
  作者：I. A. Tolmacheva、V. V. Grishko、E. I. Boreko、O. V. Savinova、N. I. Pavlova

  DOI：10.1007/s10600-009-9436-5

  日期：2009.9

  A lupane 2,3-seco-aldehydoacid that was oxidized further to the 2,3-seco-diacid was synthesized by Beckmann fragmentation of the α-hydroxyoxime of betulonic acid. It was found that both 2,3-seco-derivatives were capable of suppresing reproduction of Herpes type 1 and flu A viruses (EC50 from 1.9 to 21.3 μM).

  通过贝克曼重排反应，将桦木酮酸的α-羟基肟分解合成了A lupane 2,3-裂醛酸，并进一步氧化为2,3-裂二酸。研究发现，这两种2,3-裂衍生物均能抑制I型单纯疱疹病毒和甲型流感病毒的复制（EC50值从1.9到21.3微摩尔）。
• 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.
• The immunotropic activity of lupane and oleanane 2,3-seco-triterpenoids
  作者：L. V. Anikina、I. A. Tolmacheva、Yu. B. Vikharev、V. V. Grishko

  DOI：10.1134/s1068162010020147

  日期：2010.3

  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.