3-[((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]-propionic acid methyl ester | 521918-88-7

• 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: 3-[((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]-propionic acid methyl ester
• 英文别名: methyl 3-[[(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]propanoate
• CAS: 521918-88-7
• 化学式: C₃₄H₅₃NO₄
• 分子量: 539.799
• InChiKey: IKGSDELFCREAHW-PJGJCOAISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  39
• 可旋转键数：
  6
• 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：

  3-[((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]-propionic acid methyl ester 在 臭氧 、 溶剂黄146 、 锌 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 1.0h， 以82%的产率得到3,20-dioxo-28-(O'-methyl-β-alanino)carbonyl-29-norlupane
  参考文献：
  名称：

  Betulonic amides modified at cycle a by amino acids: Synthesis and inhibition of flu A virus reproduction

  摘要：

  The Beckman rearrangement of carboxy- and alkyloxycarbonylalkylamides of 3-hydroxyiminobetulonic acid led to derivatives of 3a-homo-4-aza-3-oxolup-20(29)-ene and 3,4-seco-2-cyanolupa-4(23),20(29)-diene. An X-ray analysis showed methyl 3-(N-acetoximino)lup-20(29)-enoate is the E-isomer. The compounds synthesized exhibited inhibiting activity toward the reproduction of flu A virus in cell culture.

  DOI：

  10.1134/s1068162009010154
• 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 3-[((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]-propionic 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

• 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
  作者：Sergey A. Popov、Marya D. Semenova、Dmitry S. Baev、Irina V. Sorokina、Natalya A. Zhukova、Tatyana S. Frolova、Tatyana G. Tolstikova、Elvira E. Shults、Māris Turks

  DOI：10.1016/j.steroids.2019.108443

  日期：2019.10

  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.