benzyl 3,O-didehydro-20,29-dihydrobetulinate | 619292-61-4

• 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: benzyl 3,O-didehydro-20,29-dihydrobetulinate
• 英文别名: benzyl dihydrobetulonate；benzyl 3-oxolupan-28-oate；(1S,3aS,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-benzyl 1-isopropyl-5a,5b,8,8,11a-pentamethyl-9-oxoicosahydro-1H-cyclopenta[a]chrysene-3a-carboxylate；benzyl (1S,3aS,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-5a,5b,8,8,11a-pentamethyl-9-oxo-1-propan-2-yl-2,3,4,5,6,7,7a,10,11,11b,12,13,13a,13b-tetradecahydro-1H-cyclopenta[a]chrysene-3a-carboxylate
• CAS: 619292-61-4
• 化学式: C₃₇H₅₄O₃
• 分子量: 546.834
• InChiKey: UFWLACBHOMIINK-SSVRXCMJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.8
• 重原子数：
  40
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  benzyl 3,O-didehydro-20,29-dihydrobetulinate 在 吡啶 、 甲醇 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 硼烷四氢呋喃络合物 、 cerium(III) chloride heptahydrate 、 palladium on activated charcoal 、 双(三甲基硅烷基)氨基钾 、 lithium bromide 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 乙醚 、 二氯甲烷 、 丙酮 为溶剂， 反应 38.33h， 生成 3β-acetoxy-2β-(3-bromopropyl)-20,29-dihydrobetulinic acid
  参考文献：
  名称：

  Synthesis of lupane triterpenoids with triphenylphosphonium substituents and studies of their antitumor activity

  摘要：

  合成了羽扇烷三萜类新衍生物，即含有三苯基鏻片段作为取代基的20,29-二氢桦木酸和3-表-20,29-二氢桦木酸衍生物。这些化合物的抗肿瘤活性大大超过桦木酸。

  DOI：

  10.1007/s11172-013-0028-y
• 作为产物：
  描述：

  白桦脂酸 在 palladium 10% on activated carbon 甲醇 、 氢气 、 potassium carbonate 、 pyridinium chlorochromate 作用下， 以 甲醇 、 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 20.0~60.0 ℃ 、310.27 kPa 条件下， 反应 25.0h， 生成 benzyl 3,O-didehydro-20,29-dihydrobetulinate
  参考文献：
  名称：

  [EN] C-28 AMIDES OF MODIFIED C-3 BETULINIC ACID DERIVATIVES AS HIV MATURATION INHIBITORS
  [FR] AMIDES C-28 DE DÉRIVÉS D'ACIDE BÉTULINIQUE MODIFIÉS EN C-3, UTILISÉS COMME INHIBITEURS DE MATURATION DU VIH

  摘要：

  具有药物和生物活性的化合物、其药物组合物及其使用方法。特别是，提供了一种具有独特抗病毒活性的改性C-3和C-28桦木酸衍生物，用作HIV成熟抑制剂。这些化合物可用于治疗HIV和艾滋病。

  公开号：

  WO2011153319A1

文献信息

• 五环三萜类化合物及其制备方法、药物组合物和用途
  申请人：中国科学院上海药物研究所

  公开号：CN109517022B

  公开（公告）日：2022-09-13

  本发明公开了一种五环三萜类化合物及其制备方法、药物组合物和用途。五环三萜类化合物的结构如通式I所示。本发明的五环三萜类化合物，能有效拮抗FXR受体，与现有的一些天然来源的FXR拮抗剂相比，具有更丰富的天然来源和更简便的合成方法。
• A Novel Secobetulinic Acid 3,4-Lactone from Viburnum aboricolum
  作者：Yuan-Ling Ku、G. Venkateswara Rao、Chung-Hsiung Chen、Chi Wu、Jih-Hwa Guh、Shoei-Sheng Lee

  DOI：10.1002/hlca.200390068

  日期：2003.3

  Bio-assay-guided fractionation of the CHCl3-soluble extract from the leaves of Viburnum aboricolum led to the isolation of a novel secobetulinic acid 3,4-lactone, viburolide (=(6β)-4,6-dihydroxy-3,4-secolup-20(29)-ene-3,28-dioic acid 3,4-lactone; 1). This is the first lupane-type compound possessing such a lactone skeleton from natural products. Its structure was elucidated by spectral analysis and

  生物测定引导的氯仿的分馏3可溶提取物的叶荚蒾aboricolum导致了新颖secobetulinic酸3,4-内酯的隔离，viburolide（=（6 β）-4,6-二羟基-3-， 4-secolup-20（29）-烯-3,28-二酸3,4-内酯; 1）。这是第一种具有这种来自天然产物的内酯骨架的紫杉烷型化合物。通过光谱分析阐明了其结构，并与由桦木酸苄酯（2）制得的6-脱羟基-20,29-二氢维布洛利（6）进行了比较。发现化合物6以12.3μM的IC 50抑制非雄激素依赖性人前列腺癌细胞（PC-3）。
• C-28 AMIDES OF MODIFIED C-3 BETULINIC ACID DERIVATIVES AS HIV MATURATION INHIBITORS
  申请人：Regueiro-Ren Alicia

  公开号：US20120142653A1

  公开（公告）日：2012-06-07

  Compounds having drug and bio-affecting properties, their pharmaceutical compositions and methods of use are set forth. In particular, modified C-3 and C-28 betulinic acid derivatives that possess unique antiviral activity are provided as HIV maturation inhibitors. These compounds are useful for the treatment of HIV and AIDS.

  本发明涉及具有药物和生物影响性质的化合物、它们的制药组合物和使用方法。具体而言，提供了具有独特的抗病毒活性的改性C-3和C-28桦酸衍生物作为HIV成熟抑制剂。这些化合物对于治疗HIV和艾滋病非常有用。
• C-28 amides of modified C-3 betulinic acid derivatives as HIV maturation inhibitors
  申请人：Regueiro-Ren Alicia

  公开号：US08802661B2

  公开（公告）日：2014-08-12

  Compounds having drug and bio-affecting properties, their pharmaceutical compositions and methods of use are set forth. In particular, modified C-3 and C-28 betulinic acid derivatives that possess unique antiviral activity are provided as HIV maturation inhibitors. These compounds are useful for the treatment of HIV and AIDS.

  本发明涉及具有药物和生物影响特性的化合物，其制药组合物和使用方法。具体而言，提供了经修饰的C-3和C-28桦酸衍生物，其具有独特的抗病毒活性，作为HIV成熟抑制剂。这些化合物可用于治疗HIV和艾滋病。
• Synthesis of cytotoxic 2,2-difluoroderivatives of dihydrobetulinic acid and allobetulin and study of their impact on cancer cells
  作者：Lucie Borkova、Lucie Jasikova、Jiri Rehulka、Katerina Frisonsova、Milan Urban、Ivo Frydrych、Igor Popa、Marian Hajduch、Niall J. Dickinson、Martin Vlk、Petr Dzubak、Jan Sarek

  DOI：10.1016/j.ejmech.2015.03.068

  日期：2015.5

  In this article, we describe the preparation and cytotoxic properties of a small focused library of lupane and 18 alpha-oleanane triterpenoids that contain a combination of two structural motifs known to enhance the biological activities. First, we introduced two fluorine atoms to position 2 of the skeleton. Second, we synthesized a set of hemiester prodrugs, which were intended to increase the solubility and activity. Starting from betulin, we obtained two hydroxyketones (derivatives of dihydrobetulinic acid and allobetulin) and their fluorination using DAST provided 2,2-difluoro-3-oxo-compounds as the main products. Then the 3-oxo group in each derivative was reduced by NaBH4 to obtain 3 beta-hydroxy compounds suitable for modifying by various hemiesters. We prepared 21 compounds, 11 of them new, their cytotoxicity was tested on T lymphoblastic leukemia CCRF-CEM cells first and the most active derivatives were selected for screening on another six tumor and two non-tumor cell lines. All of them showed selectivity against cancer lines with therapeutic index between 2 and 8. All hemiesters had activity in the same range as the free hydroxyl derivatives and they would be suitable prodrugs for future in vivo experiments. Interestingly, all hemiesters of 2,2-difluorodihydrobetulonic acid had higher activity against p53 knock-out p53-/- cancer cell line than against the non-mutated analog. In active derivatives, the cell cycle was analyzed by flow cytometry and several compounds slowed down cell cycle progression through G0/G1 or S-phase. (C) 2015 Elsevier Masson SAS. All rights reserved.