methyl 2-hydroxy-3-oxooleana-1,12-dien-28-oate | 53848-97-8

• 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: methyl 2-hydroxy-3-oxooleana-1,12-dien-28-oate
• 英文别名: methyl 2-hydroxy-3-oxo-1,2-oleandien-28-oate；methyl (4aS,6aR,6aS,6bR,8aR,12aR,14bS)-11-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-10-oxo-3,4,5,6,6a,7,8,8a,13,14b-decahydro-1H-picene-4a-carboxylate
• CAS: 53848-97-8
• 化学式: C₃₁H₄₆O₄
• 分子量: 482.704
• InChiKey: BWDRSHXGLDUFOO-CFZUYSGLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  35
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 2-hydroxy-3-oxooleana-1,12-dien-28-oate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以95%的产率得到2β,3β,28-trihydroxyolean-12-ene
  参考文献：
  名称：

  Different pathways for the deoxygenation of the A-ring of natural triterpene compounds

  摘要：

  Some deoxygenation pathways were tested to remove the hydroxyl groups of the natural triterpenes oleanolic acid and maslinic acid to obtain a practical starting material for the semisynthesis of other interesting organic synthons. Different deoxygenation processes were carried out starting from these triterpenic acids or from several derivatives such as methyl esters and epoxy derivatives. The hydroxyl groups were transformed into some intermediate compounds including xanthyl, thiocarbonyl or tosyl derivatives. The opening of the oxirane ring between C-2 and C-3 was also achieved through different methods using deoxygenating reagents such as Me3SiCl/NaI, WCl4/n-BuLi and Cp2TiCl.

  DOI：

  10.1080/14786410903172098
• 作为产物：
  描述：

  methyl 3β-acetoxy-2α-hydroxy-12-oleane-28-oate 在 jones' reagent 、 仲丁基锂 作用下， 以 四氢呋喃 、 环己烷 、 丙酮 为溶剂， 反应 4.0h， 生成 methyl 2-hydroxy-3-oxooleana-1,12-dien-28-oate
  参考文献：
  名称：

  Garcia-Granados, Andres; Duenas, Jose; Melguizo, Enrique, Journal of Chemical Research, Miniprint, 2000, # 5, p. 653 - 670

  摘要：

  DOI：

文献信息

• Novel Synthetic Oleanane and Ursane Triterpenoids with Various Enone Functionalities in Ring A as Inhibitors of Nitric Oxide Production in Mouse Macrophages
  作者：Tadashi Honda、Gordon W. Gribble、Nanjoo Suh、Heather J. Finlay、BarbieAnn V. Rounds、Lothar Bore、Frank G. Favaloro,、Yongping Wang、Michael B. Sporn

  DOI：10.1021/jm000008j

  日期：2000.5.1

  We initially randomly synthesized about 60 oleanane and ursane triterpenoids as potential anti-inflammatory and cancer chemopreventive agents. Preliminary screening of these derivatives for inhibition of production of nitric oxide induced by interferon-gamma in mouse macrophages revealed that 3-oxooleana-1, 12-dien-28-oic acid (B-15) showed significant activity (IC(50) = 5.6 microM). On the basis of

  最初，我们随机合成了约60种齐墩果烷和乌桑烷三萜作为潜在的抗炎药和癌症化学预防剂。初步筛选抑制小鼠巨噬细胞中干扰素-γ诱导的一氧化氮生成的这些衍生物，发现3-氧代油酸酯-1、12-二烯-28-酸（B-15）显示出显着的活性（IC（50）= 5.6微米）。基于B-15的结构，设计并合成了19个具有1-en-3-one官能团的，在A环的C-2处具有取代基的新颖的1-和urs-12-烯三萜。其中，在C-2处具有羧基，甲氧基羰基和腈基的3-氧代油酸酯-1,12-二烯衍生物比铅化合物B-15具有更高的活性。特别是，2-羧基-3-氧代油酸-1，12-二烯-28-油酸（3）具有最高的活性（IC（50）= 0。07 microM）中的三萜类化合物。3的效力类似于氢化可的松（IC（50）= 0.01 microM），尽管3并不通过糖皮质激素受体起作用。还讨论了这些新颖的合成三萜类化合物的有趣的构效关系。
• New enone derivatives of oleanolic acid and ursolic acid as inhibitors of nitric oxide production in mouse macrophages
  作者：Tadashi Honda、Heather J. Finlay、Gordon W. Gribble、Nanjoo Suh、Michael B. Sporn

  DOI：10.1016/s0960-894x(97)00279-5

  日期：1997.7

  New derivatives of 3-oxoolean-1-en-28 oic acid and 3-oxours-1-en-28-oic acid were synthesized. Nine of them showed significant inhibitory activity against interferon-gamma-induced nitric oxide production in mouse macrophages when assayed at the 1 mu M level. 3,12-Dioxoolean-1,9-dien-28-oic acid (3) had the highest activity (IC50, 0.9 mu M). (C) 1997 Elsevier Science Ltd.
• Different pathways for the deoxygenation of the A-ring of natural triterpene compounds
  作者：Andres Parra、Pilar E. Lopez、Andres Garcia-Granados

  DOI：10.1080/14786410903172098

  日期：2010.1.20

  Some deoxygenation pathways were tested to remove the hydroxyl groups of the natural triterpenes oleanolic acid and maslinic acid to obtain a practical starting material for the semisynthesis of other interesting organic synthons. Different deoxygenation processes were carried out starting from these triterpenic acids or from several derivatives such as methyl esters and epoxy derivatives. The hydroxyl groups were transformed into some intermediate compounds including xanthyl, thiocarbonyl or tosyl derivatives. The opening of the oxirane ring between C-2 and C-3 was also achieved through different methods using deoxygenating reagents such as Me3SiCl/NaI, WCl4/n-BuLi and Cp2TiCl.
• Garcia-Granados, Andres; Duenas, Jose; Melguizo, Enrique, Journal of Chemical Research, Miniprint, 2000, # 5, p. 653 - 670
  作者：Garcia-Granados, Andres、Duenas, Jose、Melguizo, Enrique、Moliz, Juan N.、Parra, Andres、Perez, Felipe L.

  DOI：——

  日期：——