2-hydroxyimino-11,30-dioxo-30-methoxyolean-12(13)-ene | 16844-58-9

• 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-11,30-dioxo-30-methoxyolean-12(13)-ene
• CAS: 16844-58-9
• 化学式: C₃₁H₄₅NO₅
• 分子量: 511.702
• InChiKey: NOROGQZQFLDPCS-SXRYQNKZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.15
• 重原子数：
  37.0
• 可旋转键数：
  1.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  93.03
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  2-hydroxyimino-11,30-dioxo-30-methoxyolean-12(13)-ene 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 0.75h， 以53%的产率得到3-hydroxy-2-hydroxylimino-11,30-dioxo-30-methoxyolean-12(13)-ene
  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
• 作为产物：
  描述：

  (20beta)-3,11-二氧代齐墩果-12-烯-29-酸 在 potassium tert-butylate 、 potassium carbonate 、 亚硝酸异戊酯 作用下， 以 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 7.0h， 生成 2-hydroxyimino-11,30-dioxo-30-methoxyolean-12(13)-ene
  参考文献：
  名称：

  Synthesis of Novel Heterocyclic Ring-Fused 18β-Glycyrrhetinic Acid Derivatives with Antitumor and Antimetastatic Activity

  摘要：

  Glycyrrhetinic acid (GA) is one of the most important triterpenoic acids shows many pharmacological effects, especially antitumor activity. GA triggers apoptosis in various tumor cell lines. However, the antitumor activity of GA is weak, thus the synthesis of new synthetic analogs with enhanced potency is needed. By introducing various five‐member fused heterocyclic rings at C‐2 and C‐3 positions, 18 novel GA derivatives were obtained. These compounds were evaluated for their inhibitory activity against the growth of eight different tumor cell lines using a SRB assay. The most active compound 37 showed IC50 between 5.19 and 11.72 μm, which was about 11‐fold more potent than the lead compound GA. An apoptotic effect of GA and 37 was determined using flow cytometry and trypan blue exclusion assays. We also demonstrated here for the first time that GA and the synthetic derivatives exhibited inhibitory effect on migration of the tested tumor cells, especially 37 which was about 20‐fold more potent than GA on antimetastatic activity.

  DOI：

  10.1111/cbdd.12308

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.