3β,30-di-O-acetyllup-20(29)-ene | 20065-98-9

• 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: 3β,30-di-O-acetyllup-20(29)-ene
• 英文别名: lupene-(20(29))-diyl-(3β.30)-diacetate；3β.30-Diacetoxy-lupen-(20(29))；Lupen-(20(29))-diyl-(3β.30)-diacetat；(3aR)-9c-Acetoxy-3ar.5at.5bc.8.8.11ac-hexamethyl-1t-(1-acetoxymethyl-vinyl)-(7atH.11btH.13acH.13btH)-eicosahydro-1H-cyclopenta[a]chrysen；2-[(1R,3aR,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bS)-9-acetoxy-3a,5a,5b,8,8,11a-hexamethyl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysen-1-yl]allyl acetate；2-[(1R,3aR,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bS)-9-acetyloxy-3a,5a,5b,8,8,11a-hexamethyl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysen-1-yl]prop-2-enyl acetate
• CAS: 20065-98-9
• 化学式: C₃₄H₅₄O₄
• 分子量: 526.8
• InChiKey: XNCFQJWDURPXRG-UGXCORDZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.8
• 重原子数：
  38
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3β,30-di-O-acetyllup-20(29)-ene 在 alkali 作用下， 以 水 为溶剂， 生成 Hennadiol; 29-羟基羽扇豆醇
  参考文献：
  名称：

  Isolation of dihydroxylupene and dihydroxylupane from the bark of Lawsonia inermis

  摘要：

  DOI：

  10.1016/s0031-9422(82)85077-2
• 作为产物：
  描述：

  30-bromo lupenyl acetate 在 吡啶 、 aluminum oxide 作用下， 以 苯 为溶剂， 生成 3β,30-di-O-acetyllup-20(29)-ene
  参考文献：
  名称：

  Pradhan; Chakraborty; Dutta, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1991, vol. 30, # 1, p. 32 - 37

  摘要：

  DOI：

文献信息

• Three triterpenes and other terpenoids from Catha cassinoides
  作者：C. Betancor、R. Freire、A.G. Gonzalez、J.A. Salazar、C. Pascard、T. Prange

  DOI：10.1016/0031-9422(80)83019-6

  日期：1980.1

  Abstract The investigation of stems and leaves of Catha cassinoides afforded, in addition to sitosterol, β-amyrin, ursolic acid, lup-20(29)-en-3β,30-diol and friedelin, three new pentacyclic triterpenes: 30-hydroxyfriedelan-3-one, 29-hydroxyfriedelan-3-one and 3-oxo-friedelan-29-oic acid. The structures ofthese were determined by spectral studies and correlations, and were confirmed by X-ray analysis

  摘要 对 Catha cassinoides 的茎叶进行研究，除了谷甾醇、β-香树脂醇、熊果酸、lup-20(29)-en-3β,30-diol 和 Friedelin 外，还提供了三种新的五环三萜：30-羟基弗里德兰- 3-one、29-hydroxyfriedelan-3-one 和 3-oxo-friedelan-29-oic 酸。这些结构由光谱研究和相关性确定，并通过 29-羟基弗里德兰-3-一醋酸盐的 X 射线分析证实。
• Zur Kenntnis der Triterpene. (48. Mitteilung). Über Oxydationsprodukte des Lupeols und von Estern des Lupeols mit Phtalmonopersäure und mit Selendioxyd
  作者：L. Ruzicka、G. Rosenkranz

  DOI：10.1002/hlca.19390220196

  日期：——
• Isolation, Structural Modification, and HIV Inhibition of Pentacyclic Lupane-Type Triterpenoids from <i>Cassine xylocarpa</i> and <i>Maytenus cuzcoina</i>
  作者：Oliver Callies、Luis M. Bedoya、Manuela Beltrán、Alejandro Muñoz、Patricia Obregón Calderón、Alex A. Osorio、Ignacio A. Jiménez、José Alcamí、Isabel L. Bazzocchi

  DOI：10.1021/np501025r

  日期：2015.5.22

  As a part of our investigation into new anti-HIV agents, we report herein the isolation, structure elucidation, and biological activity of six new (1-6) and 20 known (7-26) pentacyclic lupane-type triterpenoids from the stem of Cassine xylocarpa and root bark of Maytenus cuzcoina. Their stereo-structures were elucidated on the basis of spectroscopic and spectrometric methods, including ID and 2D NMR techniques. To gain a more complete understanding of the structural requirements for anti-HIV activity, derivatives 27-48 were prepared by chemical modification of the main secondary metabolites. Sixteen compounds from this series displayed inhibitory effects of human immunodeficiency virus type 1 replication with IC50 values in the micromolar range, highlighting compounds 12, 38, and 42 (IC50 4.08, 4.18, and 1.70 mu M, respectively) as the most promising anti-HIV agents.
• 135. The constitution of lupeol
  作者：E. R. H. Jones、R. J. Meakins

  DOI：10.1039/jr9410000757

  日期：——
• Simonsen,J.; Ross,W. C. J., The Terpenes, Bd. 4 <Cambridge 1957> S. 346
  作者：Simonsen,J.、Ross,W. C. J.

  DOI：——

  日期：——