messagenin | 18211-63-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: messagenin
• 英文别名: 30-norlupane-3β,28-diol-20-one；1-[(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bS)-9-hydroxy-3a-(hydroxymethyl)-5a,5b,8,8,11a-pentamethyl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysen-1-yl]ethanone
• CAS: 18211-63-7
• 化学式: C₂₉H₄₈O₃
• 分子量: 444.698
• InChiKey: BSALBDFYJLSIOZ-UGWIBKDRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  32
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  messagenin 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以60%的产率得到(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bS)-1-((R)-1-Hydroxy-ethyl)-3a-hydroxymethyl-5a,5b,8,8,11a-pentamethyl-icosahydro-cyclopenta[a]chrysen-9-ol
  参考文献：
  名称：

  Synthesis of O- and N-Aminopropyltriterpenoids Based on Messagenin

  摘要：

  通过20R-羟基和20E-羟基亚氨基美塞素衍生物的连续氰乙基化和还原反应，合成了在羽扇烷C-3、C-20和C-28位置带有O-和N-氨基丙基片段的三萜类化合物。

  DOI：

  10.1007/s10600-018-2511-z
• 作为产物：
  描述：

  白桦脂酸 在 lithium aluminium tetrahydride 、 二甲基硫 、 臭氧 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 messagenin
  参考文献：
  名称：

  Potential allelopathic lupane triterpenes from bioactive fractions of melilotus messanensis*

  摘要：

  The aerial parts of Melilotus messanenis (sweet clover) afforded, from the medium polar bioactive fractions, in addition to the known lupane triterpenes lupeol, betulin, betulin aldehyde and betulinic acid, the new norlupane messagenin (30-norlupane-3 beta,28-diol-20-one) which have been tested as allelochemicals. Structures and their stereochemistries were elucidated by spectral methods and chemical transformations. Messagenin has been synthesized from betulinic acid. The effect of a series of aqueous solutions at 10(-4)-10(-9) M of eight natural and synthetic lupane derivatives were tested for their effects on the germination and growth of the dicotyledon species Lactuca sativa and Lepidium sativum and the monocotyledon species Hordeum vulgare and Triticum aestivum. All eight lupane triterpenes possess potential allelopathic activity in particular over dicotyledon species and they are likely to be significantly involved in the allelopathic action of Melilotus messanensis.

  DOI：

  10.1016/s0031-9422(00)89726-5

文献信息

• Synthesis of triterpenoid acylates: Effective reproduction inhibitors of influenza A (H1N1) and papilloma viruses
  作者：O. B. Kazakova、N. I. Medvedeva、I. P. Baikova、G. A. Tolstikov、T. V. Lopatina、M. S. Yunusov、L. Zaprutko

  DOI：10.1134/s1068162010060142

  日期：2010.11

  The synthesis of a new group of triterpenoid acylates has been conducted on the basis of oleanolic, glycyrrhetic, and ursolic acids and betulin. 28-ortho-Methoxycynnamoylbetulin has been demonstrated to possess high activity against the influenza type A (H1N1) virus with the selectivity index SI > 100 while studying the activity of the synthesized compounds in relation to the reproduction of viral

  以齐墩果酸、甘草次酸、熊果酸和桦木脑为基础合成了一组新的三萜酰化物。在研究合成化合物与呼吸道感染病毒病原体繁殖相关的活性时，28-ortho-Methoxycynnamoylbetulin 已被证明对甲型流感 (H1N1) 病毒具有高活性，选择性指数 SI > 100。3,28-二烟酰桦木素对乳头状瘤病毒（HPV-11 株）具有高活性，选择性指数 SI 35。
• Zur Kenntnis der Triterpene. (55. Mitteilung). Über Oxydationsprodukte von Betulin und von Betulin-diacetat
  作者：L. Ruzicka、M. Brenner

  DOI：10.1002/hlca.194002301156

  日期：——
• Zur Kenntnis der Triterpene. (64. Mitteilung). Abbau des Betulin-diacetats mit Ozon
  作者：L. Ruzicka、Ed. Rey

  DOI：10.1002/hlca.19420250118

  日期：1942.2.2
• Selective Oxidation of Triterpene Alcohols by Sodium Hypochlorite
  作者：O. B. Flekhter、O. Yu. Ashavina、I. E. Smirnova、L. A. Baltina、F. Z. Galin、N. N. Kabal'nova、G. A. Tolstikov

  DOI：10.1023/b:conc.0000033930.76751.b7

  日期：2004.3

  3-Oxo-triterpenoids were prepared by oxidation of the methyl esters of glycyrrhetic acid, allobetulin, and 20-oxo-29-nor-betulin with sodium hypochlorite in acetic acid or methylene chloride under phase-transfer conditions.
• Vystrcil,A.; Budesinsky,M., Collection of Czechoslovak Chemical Communications, 1970, vol. 35, p. 295 - 311
  作者：Vystrcil,A.、Budesinsky,M.

  DOI：——

  日期：——