3,28-O,O'-dipropanoylbetulin | 5956-67-2

• 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: 3,28-O,O'-dipropanoylbetulin
• 英文别名: betulin dipropionate；[(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-5a,5b,8,8,11a-pentamethyl-9-propanoyloxy-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 propanoate
• CAS: 5956-67-2
• 化学式: C₃₆H₅₈O₄
• 分子量: 554.854
• InChiKey: YRYFZBMPOBLGMK-SCWDCIOVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.4
• 重原子数：
  40
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.89
• 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：

  3,28-O,O'-dipropanoylbetulin 在 溴 、 臭氧 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 26.0h， 生成 30-bromo-20-oxo-29-norlupane-3β,28-diyl dipropanoate
  参考文献：
  名称：

  Synthesis of 30-Bromo- and 30-Azido-20-oxo-29-nor-3β,28-diacylbetulin Derivatives

  摘要：

  Ozonolysis of 3 beta, 28-diacyloxylup-20,29-enes gave 20-oxo-29-nor-3 beta,28-diacyloxylup-20,29-enes, which were brominated with molecular bromine in AcOH to obtain a mixture of 30-bromo- and 30-dibromo derivatives. Ozonolysis of 30-bromo-3 beta,28-diacylbetulin produced 29-nor-30-bromoketones, whose reaction with sodium azide afforded 29-nor-30-azidoketones of the lupane series.

  DOI：

  10.1134/s1070428019110150
• 作为产物：
  描述：

  白桦脂醇 、 丙酸酐 在 吡啶 、 4-二甲氨基吡啶 作用下， 反应 1.0h， 以10.08 g的产率得到3,28-O,O'-dipropanoylbetulin
  参考文献：
  名称：

  Ferrocenyltriazoles from 3β,28-Diacylbetulin: Synthesis and Cytotoxic Activity

  摘要：

  The reaction of 30-bromo-3 beta,28-diacylbetulin with sodium azide afforded 30-azido-3 beta,28-diacyloxylup-20(29)-enes. The products were subjected to a CuI/TMEDA-catalyzed click reaction with ethynylferrocene to obtain the corresponding ferrocene-betulin conjugates with a 1,2,3-triazole linker.

  DOI：

  10.1134/s1070428019110083

文献信息

• Synthesis, Structure and Cytotoxic Activity of New Acetylenic Derivatives of Betulin
  作者：Stanisław Boryczka、Ewa Bębenek、Joanna Wietrzyk、Katarzyna Kempińska、Maria Jastrzębska、Joachim Kusz、Maria Nowak

  DOI：10.3390/molecules18044526

  日期：——

  A new series of betulin derivatives containing one or two pharmacophores bearing an acetylenic and carbonyl function at the C-3 and/or C-28 positions has been synthesized and characterized by 1H- and 13C-NMR, IR, MS and elemental analyses. The crystal structure of 28-O-propynoylbetulin was determined by X-ray structural analysis. All new compounds, as well as betulin, were tested in vitro for their antiproliferative activity against human SW707 colorectal, CCRF/CEM leukemia, T47D breast cancer, and against murine P388 leukemia and Balb3T3 normal fibroblasts cell lines. Most of the compounds showed better cytotoxicity than betulin and cisplatin used as reference agent. 28-O-Propynoylbetulin was the most potent derivative, being over 500 times more potent than betulin and about 100 times more cytotoxic than cisplatin against the human leukemia (CCRF/CEM) cell line, with an ID50 value of 0.02 μg/mL.

  一种新的含有一个或两个药效团的贝图林衍生物已被合成，这些药效团在C-3和/或C-28位置上具有炔烃和羰基功能。通过高分辨率的1H-NMR、13C-NMR、红外光谱、质谱以及元素分析对其进行了表征。28-O-丙炔酰贝图林的晶体结构通过X射线结构分析确定。所有新的化合物以及贝图林在体外测试了其对人SW707结肠癌、CCRF/CEM白血病、T47D乳腺癌及小鼠P388白血病和Balb3T3正常成纤维细胞株的抗增殖活性。大多数化合物的细胞毒性优于作为参考药物的贝图林和顺铂。28-O-丙炔酰贝图林是最有效的衍生物，其活性比贝图林强超过500倍，对人白血病（CCRF/CEM）细胞株的细胞毒性约为顺铂的100倍，ID50值为0.02 μg/mL。
• Photoinduced Oxygen Transfer Using Nitroarenes for the Anaerobic Cleavage of Alkenes
  作者：Dan E. Wise、Emma S. Gogarnoiu、Alana D. Duke、Joshua M. Paolillo、Taylor L. Vacala、Waseem A. Hussain、Marvin Parasram

  DOI：10.1021/jacs.2c05648

  日期：2022.8.31

  Mechanistic studies support that the transformation occurs via direct photoexcitation of the nitroarene followed by a nonstereospecific radical cycloaddition event with alkenes. This leads to 1,3,2- and 1,4,2-dioxazolidine intermediates that fragment to give the carbonyl products. A combination of radical clock experiments and in situ photoNMR spectroscopy revealed the identities of the key radical species

  在这里，我们报告了在可见光下使用硝基芳烃作为氧转移试剂将烯烃厌氧裂解成羰基化合物。这种方法可作为主流氧化裂解方案（如臭氧分解和 Lemieux-Johnson 反应）的安全且实用的替代方案。具有氧化敏感性官能团的多种烯烃经历厌氧裂解以产生具有高效率和区域选择性的羰基衍生物。机理研究支持通过硝基芳烃的直接光激发以及随后与烯烃的非立体特异性自由基环加成反应发生转化。这导致 1,3,2- 和 1,4,2-二恶唑烷中间体断裂以产生羰基产物。激进时钟实验和原位实验的结合光核磁共振光谱分别揭示了关键自由基物种和推定的芳基二恶唑烷中间体的身份。
• Über die Sterine der Rinde von Lophopetalum toxicum
  作者：H. Dieterle、H. Leonhardt、K. Dorner

  DOI：10.1002/ardp.19332710408

  日期：——
• THERAPEUTIC TRITERPENOIDS
  申请人：Krasutsky Pavel A.

  公开号：US20090136566A1

  公开（公告）日：2009-05-28

  The present invention relates generally to compositions that can be obtained by extraction of birch bark, methods of using such compositions (e.g., methods of medical use, cosmetic use and/or pharmaceutical use), food products and methods of manufacturing such compounds. The compositions are triterpenes, triterpene alcohols, or derivatives of triterpene alcohols.