3β,28-dihydroxylup-20(29)-en-30-al | 18303-59-8

• 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-dihydroxylup-20(29)-en-30-al
• 英文别名: betuline acrylaldehyde；3β,28-Dihydroxy-lupenal；lup-20(29)-en-3b,28-diol-30-al；lup-20(30)-en-3β,28-diol-29-al；3β.28-dihydroxy-lupen-(20(29))-al-(30)；2-[(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]prop-2-enal
• CAS: 18303-59-8
• 化学式: C₃₀H₄₈O₃
• 分子量: 456.709
• InChiKey: UTUUDDODKUTNLS-ROUWMTJPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  33
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.9
• 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：

  3β,28-dihydroxylup-20(29)-en-30-al 在 乙酸酐 作用下， 以 吡啶 、 氯仿 为溶剂， 反应 12.0h， 以72%的产率得到3β-hydroxy-28-acetoxy-lup-20(29)-en-30-al
  参考文献：
  名称：

  Synthesis of bioactive 28-hydroxy-3-oxolup-20(29)-en-30-al with antileukemic activity

  摘要：

  An easy and efficient route to partial synthesis of bioactive 28-hydroxy-3-oxolup20( 29)-en-30-al (1), starting from betulinic acid (2), has been developed (eight steps, 44% overall yield). Structures of all the compounds were determined by spectral studies (IR, H-1, C-13 NMR, MS, NOESY, COSY, etc.). Compound 1 and the precursors (2, 3, 5, and 7) showed antiproliferative activities against human K562 leukemia, murine WEHI3 leukemia, and murine MEL erythroid progenitor.

  DOI：

  10.1080/10286020.2011.640774
• 作为产物：
  描述：

  白桦脂醇 在 selenium(IV) oxide 作用下， 以 二氯甲烷 为溶剂， 以30 %的产率得到3β,28-dihydroxylup-20(29)-en-30-al
  参考文献：
  名称：

  羽扇豆衍生物：针对恶性疟原虫 3D7 株的抗疟原虫活性的设计、分离、合成和评估

  摘要：

  为了寻找对抗疟疾的先导化合物，通过针对恶性疟原虫的酶标靶甘油醛-3-磷酸脱氢酶 (P f GAPDH) 的分子对接研究，筛选了来自喀麦隆天然产物库 (CANAPL)的化合物。对接命中包括羽扇豆醇肉桂酸酯 ( 1 ) 和齐墩果烷肉桂酸酯 ( 2 )。从Baillonella toxisperma (Pierre)中分离出与( 1 )和( 2 )结构相似的三萜类化合物；齐墩果-12-en-3β-癸酸酯 ( 3 )、3-β-反式肉桂酰氧基lup-20(29)-烯 ( 4 ) 、 3β-香树脂醇乙酸酯 ( 5)、蒲公英醇 ( 6 )、桦木酮酸 ( 7 )、β-谷甾醇 ( 8 )、桦木酸 ( 9 )、3β-(反式对香豆酰基)oxylup-20(29)-en-28-oïc 酸 ( 10 ）并与桦木碱（11 ）和齐墩果酸（12）一起筛选。对恶性疟原虫3D7 菌株具有 100% 生长抑制作用的有利化合物7和10与化合物

  DOI：

  10.1016/j.phytol.2023.06.009

文献信息

• Synthesis and Anti-HIV Activity of Lupane and Olean-18-ene Derivatives. Absolute Configuration of 19,20-Epoxylupanes by VCD
  作者：Fátima Gutiérrez-Nicolás、Bárbara Gordillo-Román、Juan C. Oberti、Ana Estévez-Braun、Ángel G. Ravelo、Pedro Joseph-Nathan

  DOI：10.1021/np200910u

  日期：2012.4.27

  Lupane triterpenoids 2 and 5-12 and oleanene derivatives 13 and 14 were prepared from lupeol (1), betulin (3), and germanicol (4). They were tested for anti-HIV activity, and some structure-activity relationships were outlined. The 20-(S) absolute configuration of epoxylupenone (8) was assessed by comparison of the observed and DFT-calculated vibrational circular dichroism spectra. The CompareVOA algorithm was employed to support the C-20 configuration assignment. The 20,29 double bond in lupenone (2) and 3-epilupeol (15) was stereoselectively epoxidized to produce 20-(S)-8 and 20-(S)-16, respectively, an assignment in agreement with their X-ray diffraction structures.
• Zur Kenntnis der Triterpene. (63. Mitteilung). Oxydation von Betulin-diacetat mit Phthalmonopersäure und mit Selendioxyd
  作者：L. Ruzicka、M. Brenner、Ed. Rey

  DOI：10.1002/hlca.19420250117

  日期：1942.2.2
• Synthesis of bioactive 28-hydroxy-3-oxolup-20(29)-en-30-al with antileukemic activity
  作者：Pranab Ghosh、Amitava Mandal、Joydip Ghosh、Chiranjib Pal、Ashis Kumar Nanda

  DOI：10.1080/10286020.2011.640774

  日期：2012.2.1

  An easy and efficient route to partial synthesis of bioactive 28-hydroxy-3-oxolup20( 29)-en-30-al (1), starting from betulinic acid (2), has been developed (eight steps, 44% overall yield). Structures of all the compounds were determined by spectral studies (IR, H-1, C-13 NMR, MS, NOESY, COSY, etc.). Compound 1 and the precursors (2, 3, 5, and 7) showed antiproliferative activities against human K562 leukemia, murine WEHI3 leukemia, and murine MEL erythroid progenitor.
• Lupane derivatives: Design, isolation, synthesis and evaluation of antiplasmodial activity against Plasmodium falciparum 3D7 strain
  作者：Pierre Yemback、Kenneth O. Eyong、Noella M. Efange、Michael HK. Kamdem、Derek T. Ndinteh、Patricia O. Odumosu、Gabriel N. Folefoc、Lawrence Ayong、Thomas Werner

  DOI：10.1016/j.phytol.2023.06.009

  日期：2023.10

  (Pierre); olean-12-en-3β-decanoate (3), 3-β-trans cinnamoyloxylup-20(29)-ene (4), 3β-amyrin acetate (5), taraxerol (6), betulonic acid (7), β-sitosterol (8), betulinic acid (9), 3β-(trans-p-Coumaroyl)oxylup-20(29)-en-28-oïc acid (10) and screened alongside Betuline (11) and oleanolic acid (12). The favorable compounds 7 and 10 with 100 % growth inhibition on P. falciparum 3D7 strain together with compounds

  为了寻找对抗疟疾的先导化合物，通过针对恶性疟原虫的酶标靶甘油醛-3-磷酸脱氢酶 (P f GAPDH) 的分子对接研究，筛选了来自喀麦隆天然产物库 (CANAPL)的化合物。对接命中包括羽扇豆醇肉桂酸酯 ( 1 ) 和齐墩果烷肉桂酸酯 ( 2 )。从Baillonella toxisperma (Pierre)中分离出与( 1 )和( 2 )结构相似的三萜类化合物；齐墩果-12-en-3β-癸酸酯 ( 3 )、3-β-反式肉桂酰氧基lup-20(29)-烯 ( 4 ) 、 3β-香树脂醇乙酸酯 ( 5)、蒲公英醇 ( 6 )、桦木酮酸 ( 7 )、β-谷甾醇 ( 8 )、桦木酸 ( 9 )、3β-(反式对香豆酰基)oxylup-20(29)-en-28-oïc 酸 ( 10 ）并与桦木碱（11 ）和齐墩果酸（12）一起筛选。对恶性疟原虫3D7 菌株具有 100% 生长抑制作用的有利化合物7和10与化合物