3β,28,30-Lup-20(29)-enetriol | 20065-97-8

• 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,28,30-Lup-20(29)-enetriol
• 英文别名: 3β,28,30-trihydroxylup-20(29)-ene；10-hydroxybetulin；30-hydroxybetulin；lup-20(29)-ene-3β,28,30-triol；(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bS)-3a-(hydroxymethyl)-1-[1-(hydroxymethyl)vinyl]-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-9-ol；(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bS)-3a-(hydroxymethyl)-1-(3-hydroxyprop-1-en-2-yl)-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-9-ol
• CAS: 20065-97-8
• 化学式: C₃₀H₅₀O₃
• 分子量: 458.725
• InChiKey: XTNACZMKNVUNAA-ROUWMTJPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  33
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 3β,28,30-Lup-20(29)-enetriol 在 吡啶 作用下， 反应 14.0h， 以37 mg的产率得到3β,28,30-triacetoxylup-20(29)-ene
  参考文献：
  名称：

  Maytenus canariensis 三萜类化合物及桦木脑衍生物的合成

  摘要：

  摘要 从 Maytenus canariensis 中分离到了新的三萜类化合物 3β,28,30-lup-20(29)ene-triol 和 28,30-dihydroxy-lup-20(29)-en-3-one 并通过方法确定了它们的结构。光谱研究和化学相关性。第一种三萜的衍生物是由桦木脑 [3β,28-lup-20(29)ene-diol] 部分合成的。

  DOI：

  10.1016/0031-9422(92)80365-l
• 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 3β,28,30-Lup-20(29)-enetriol
  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

• Anti-AIDS Agents. 34. Synthesis and Structure−Activity Relationships of Betulin Derivatives as Anti-HIV Agents
  作者：I-Chen Sun、Hui-Kang Wang、Yoshiki Kashiwada、Jing-Kang Shen、L. Mark Cosentino、Chin-Ho Chen、Li-Ming Yang、Kuo-Hsiung Lee

  DOI：10.1021/jm980391g

  日期：1998.11.1

  followed by 3',3'-tetramethylene glutaryl derivatives (10 > 9 > 11 > 12, 18 > 17 > 19 > 20). The most potent compound, 10, has two 3',3'-dimethylglutaryl groups and displays significant anti-HIV potency with an EC50 value of 0.000 66 microM and a TI of 21 515. Results for compounds (22 and 23) without a C-3 acyl group confirmed the importance of the C-3 acyl group to the anti-HIV effect. With 3',3'-tetramethylene

  琥珀酰和3'-取代的戊二酰桦木酚衍生物比二氢白桦木衍生物具有更强的抗HIV活性和更高的治疗指数（TI）值，比率为1.2：1至15：1（参见7和15、9、17、10和10）和18、11和19，以及12和20）。对于各种3'-取代的戊二酰化合物，从强抑制到弱抑制的抗HIV效应顺序为3'，3'-二甲基，3'-甲基，3'-乙基-3'-甲基，然后是3 '，3'-四亚甲基戊二酰芳基衍生物（10> 9> 11> 12、18> 17> 19> 20）。最有效的化合物10具有两个3'，3'-二甲基戊二烯基，并显示出显着的抗HIV效能，EC50值为0.000 66 microM，TI为21515。没有C-3酰基的化合物（22和23）的结果证实了C-3酰基对抗HIV作用的重要性。使用3'，3'-四亚甲基戊二酰戊二烯衍生物，三酰基29显示出比二酰基12更强的抑制作用；相反，3'，3'-二甲基戊二烯基化合物显示相反的结果。3-酮化合物（35和36）和2
• Lupane-Type Triterpenoids Modified at 30-Position and Analogues Thereof
  申请人：Koohang Ali

  公开号：US20090062243A1

  公开（公告）日：2009-03-05

  The present invention comprises lupine-type triterpenoids that inhibit cell proliferations, in particular cancer and conditions associated with cancer. For example, associated malignancies include ovarian cancer, cervical cancer, breast cancer, colorectal cancer, and glioblastomas, among others. Accordingly, the compounds of the present invention are useful for treating, preventing, and/or inhibiting these diseases. Thus, the present invention also comprising pharmaceutical formulations comprising the compounds and methods of using the compounds and formulations to inhibit cancer and treat, prevent, or inhibit the foregoing diseases.

  本发明涉及一种羽扇豆型三萜类物质，可抑制细胞增殖，特别是癌症和与癌症相关的疾病。例如，相关的恶性肿瘤包括卵巢癌、宫颈癌、乳腺癌、结直肠癌和胶质母细胞瘤等。因此，本发明的化合物可用于治疗、预防和/或抑制这些疾病。因此，本发明还包括含有这些化合物的药物配方和使用这些化合物和配方抑制癌症和治疗、预防或抑制上述疾病的方法。
• Allylic Hydroxylation Through Acid Catalysed Epoxy Ring Opening of Betulinic Acid Derivatives
  作者：Swapan Pramanick、Suparna Mandal、Sibabrata Mukhopadhyay、Sailen Jha

  DOI：10.1080/00397910500180568

  日期：2005.8.1

  Acid catalysed epoxy ring opening of several lupane type triterpenoids leads to unusual allylic hydroxylation. The reaction involves the formation of epoxide by m-chloroperbenzoic acid followed by the treatment of mineral acid. The simple methodology finds utility to introduce a hydroxyl function at the allylic position in these triterpenoids, which is otherwise quite difficult.
• First Synthesis of Betulin 20-Acylhydrazones
  作者：Yu. V. Myasoedova、E. R. Belyaeva、L. R. Garifullina、D. A. Prosvirnina、G. Yu. Ishmuratov

  DOI：10.1134/s1070428022010109

  日期：2022.1
• [EN] LUPANE-TYPE TRITERPENOIDS MODIFIED AT 30-POSITION AND ANALOGUES THEREOF<br/>[FR] TRITERPÉNOÏDES DE TYPE LUPANE MODIFIÉS EN POSITION 30 ET LEURS ANALOGUES
  申请人：ADVANCED LIFE SCIENCES INC

  公开号：WO2009020732A1

  公开（公告）日：2009-02-12

  The present invention comprises lupine-type triterpenoids that inhibit cell proliferations, in particular cancer and conditions associated with cancer. For example, associated malignancies include ovarian cancer, cervical cancer, breast cancer, colorectal cancer, and glioblastomas, among others. Accordingly, the compounds of the present invention are useful for treating, preventing, and/or inhibiting these diseases. Thus, the present invention also comprising pharmaceutical formulations comprising the compounds and methods of using the compounds and formulations to inhibit cancer and treat, prevent, or inhibit the foregoing diseases.