[((1R,3aS,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-1-Isopropenyl-5a,5b,8,8,11a-pentamethyl-9-oxo-icosahydro-cyclopenta[a]chrysene-3a-carbonyl)-amino]-acetic acid methyl ester | 521919-00-6

• 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: [((1R,3aS,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-1-Isopropenyl-5a,5b,8,8,11a-pentamethyl-9-oxo-icosahydro-cyclopenta[a]chrysene-3a-carbonyl)-amino]-acetic acid methyl ester
• 英文别名: methyl 2-[[(1R,3aS,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-5a,5b,8,8,11a-pentamethyl-9-oxo-1-prop-1-en-2-yl-2,3,4,5,6,7,7a,10,11,11b,12,13,13a,13b-tetradecahydro-1H-cyclopenta[a]chrysene-3a-carbonyl]amino]acetate
• CAS: 521919-00-6
• 化学式: C₃₃H₅₁NO₄
• 分子量: 525.772
• InChiKey: IJLHFJQECNLTGR-HYJPRLOJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  38
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  72.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [((1R,3aS,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-1-Isopropenyl-5a,5b,8,8,11a-pentamethyl-9-oxo-icosahydro-cyclopenta[a]chrysene-3a-carbonyl)-amino]-acetic acid methyl ester 在 potassium carbonate 、 potassium iodide 、 sodium hydroxide 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 (5-(4-bromophenyl)-1,3,4-oxadiazole-2-yl)methyl-N-(3-oxolup-20(29)-en-28-oyl)-2-aminoethanoate
  参考文献：
  名称：

  Lupane-type conjugates with aminoacids, 1,3,4- oxadiazole and 1,2,5-oxadiazole-2-oxide derivatives: Synthesis, anti-inflammatory activity and in silico evaluation of target affinity

  摘要：

  With the purpose to improve anti-inflammatory activity, the impact of introduction of 1,2,5- and 1,3,4-oxadiazole fragments to betulonic acid core as well as hybrids tethered with short to-amino acids has been studied. The anti-inflammatory activity of synthesized compounds was tested in vivo using models of inflammation induced by concanavalin A and histamine. The majority of new compounds demonstrated higher anti-inflammatory activity compared with starting betulonic acid. To confirm the molecular targets of new derivatives in NRf2 and NF kappa B pathways the docking at Kelch and BTB active sites of Keap1 as well as IKK was done. The novelty of the present work is the development of new class of low toxic anti-inflammatory substances consisting of amino acid-linked betulonic acid - oxadiazole conjugates. These compounds can be considered as prospective chemopreventive agents.

  DOI：

  10.1016/j.steroids.2019.108443
• 作为产物：
  描述：

  桦木脑二乙酸 在 sodium hydroxide 、 jones reagent 、 草酰氯 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 168037.0h， 生成 [((1R,3aS,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-1-Isopropenyl-5a,5b,8,8,11a-pentamethyl-9-oxo-icosahydro-cyclopenta[a]chrysene-3a-carbonyl)-amino]-acetic acid methyl ester
  参考文献：
  名称：

  摘要：

  New derivatives of betulonic acid containing on C-28 fragments of amino acids or their methyl esters were prepared as potential biologically active agents.

  DOI：

  10.1023/a:1021621907515

文献信息

• Synthesis of novel bioconjugates of α-tocopherol with lupane triterpenoids
  作者：A. Yu. Spivak、R. R. Mufazzalova、E. R. Shakurova、V. N. Odinokov、U. M. Dzhemilev

  DOI：10.1007/s11172-010-0069-4

  日期：2010.1

  The first representatives of gA-tocopherol bioconjugates with lupane triterpenoids were synthesized using amino acid residues and dipeptides as linkers between the antioxidant molecule and the terpenoid C(28) atom. The synthetic combination of natural compounds was carried out by the reaction of lupane acid chlorides (betulonic and betulinic acid chlorides) with amino acid and dipeptide derivatives of gA-tocopherol.

  利用氨基酸残基和二肽作为抗氧化剂分子与萜类化合物 C（28）原子之间的连接体，合成了 gA-生育酚与羽扇豆三萜类化合物生物共轭物的首个代表。羽扇豆酸氯化物（桦木酸和桦木酸氯化物）与 gA-生育酚的氨基酸和二肽衍生物发生反应，从而实现了天然化合物的合成组合。