28-O-(3,4,5-trimethoxybenzoyl)betulin | 1342314-56-0

• 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: 28-O-(3,4,5-trimethoxybenzoyl)betulin
• 英文别名: (3β)-3-hydroxy-28-3,4,5-trimethoxyphenacyl-20(29)-lupaene；betulin 28-O-3,4,5-trimethoxybenzoate；[(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-hydroxy-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysen-3a-yl]methyl 3,4,5-trimethoxybenzoate
• CAS: 1342314-56-0
• 化学式: C₄₀H₆₀O₆
• 分子量: 636.913
• InChiKey: ZWORIMRLTXNVSO-NUAMVBRNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.4
• 重原子数：
  46
• 可旋转键数：
  8
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  白桦脂醇 、 3,4,5-三甲氧基苯甲酸 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 24.0h， 以39.1%的产率得到28-O-(3,4,5-trimethoxybenzoyl)betulin
  参考文献：
  名称：

  Synthesis of triterpenoid derivatives and their anti-tumor and anti-hepatic fibrosis activities

  摘要：

  Oleanolic acid (1), ursolic acid (2), hederagenin (3), betulinol (4), betulinic acid (5), and glycyrrhetinic acid (6) are obtained from acorn/licorice industrial wastes with common triterpenoid structure as a model set for esterification. Eight 3,4,5-methoxybenzoyl triterpenoid derivatives (1a-6a), including four new derivatives (1a, 3a-1, 3a-2, and 3a-3), are synthesized by classical procedures. Their antitumor and anti-hepatic fibrosis activities are evaluated on four human tumor cell lines and t-HSC/Cl-6 cells. Derivative 1a shows maximum antiproliferative effects against all cell lines, especially against tumor cells with IC50 values in the range of 5.32-15.23 mu M, but does not affect the viability of normal cells. The anti-tumor mechanisms of 1a are also investigated by western blot and docking studies. The 3,4,5-methoxybenzoyl triterpenoids offers an intriguing solution for naturally derived antitumor drugs and may be invaluable for further development of cancer therapy.

  DOI：

  10.1080/14786419.2018.1499642

文献信息

• Betulin esters with coumarin-3-carboxylic and 3,4,5-trimethoxybenzoic acids
  作者：Ge-Yang Wang、Lei Jin、Feng-Yu Piao、Rong-Bi Han

  DOI：10.1016/j.mencom.2017.01.030

  日期：2017.1

  Direct esterification of betulin with coumarin-3-carboxylic or 3,4,5-trimethoxybenzoic acid led to betulin-28-esters and betulin-3,28-diesters. The betulin-3-esters were synthesized through 28-O-protection, esterification and deprotection steps using betulin as a starting material.

  桦木素与香豆素-3-羧酸或3,4,5-三甲氧基苯甲酸的直接酯化导致桦木素28-酯和桦木素-3,28-二酯。使用白蛋白作为起始原料，通过28-O-保护，酯化和脱保护步骤合成了白蛋白3-酯。
• Synthesis and antibacterial activity of betulin esters
  作者：K.-T. Chue、M.-S. Chang、L. N. Ten

  DOI：10.1007/s10600-011-0001-7

  日期：2011.9

  Betulin isonicotinate, 6-chloronicotinate, 2-chlorocinnamate, and benzoates were synthesized by the reaction of betulin and the acid chlorides. It was shown that the 3,4-difluorobenzoate exhibited antibacterial activity against Ochrobactrum anthropi, Stenotrophomonas maltophilia, and S. nitritireducens whereas the 3,5-dinitrobenzoate was active against the last two microorganisms.

  通过倍半醇与酸氯化物反应合成了倍半醇异烟酸酯、6-氯烟酸酯、2-氯肉桂酸酯和苯甲酸酯。研究表明，3,4-二氟苯甲酸酯对人类黄杆菌、斯地诺特罗莫纳斯和硝酸盐还原微生物S. nitritireducens具有抗菌活性，而3,5-二硝基苯甲酸酯则对后两种微生物有效。