2,3,4,6-tetra-O-acetyl β-D-glucopyranosyl-3β-hydroxylup-20(29)-en-28-oate | 22333-86-4

• 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: 2,3,4,6-tetra-O-acetyl β-D-glucopyranosyl-3β-hydroxylup-20(29)-en-28-oate
• 英文别名: [(2S,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl] (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-hydroxy-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carboxylate
• CAS: 22333-86-4
• 化学式: C₄₄H₆₆O₁₂
• 分子量: 787.001
• InChiKey: BLHFTTIPQRRXJP-LKOYHKRESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  56
• 可旋转键数：
  13
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  161
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  2,3,4,6-tetra-O-acetyl β-D-glucopyranosyl-3β-hydroxylup-20(29)-en-28-oate 在 氢氧化钾 、 silver(l) oxide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 53.0h， 生成 betulinic acid 3-O-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of Glycosides of Lupane-Type Triterpene Acids

  摘要：

  A preparative synthesis of glucosides of the lupane-type triterpene acids betulinic, dihydrobetulinic, betulonic, dihydrobetulonic. and 3,20-dioxo-30-norlupan-28-oic was proposed. Glycosylation of 3-hydroxyacids by alpha-acetohronioglucose (ABG) with Ag2O was performed in pyridine (Py) to form glycosides at C-28, repeated glycosylation of which by these same reagents but in CH2Cl2 generated a glycoside bond at C-3 to form bisglucosides 28- Glucosides of ketoacids were formed in high yields in both Py and CH2Cl2.

  DOI：

  10.1023/b:conc.0000018113.79735.34
• 作为产物：
  描述：

  3Beta-乙酰氧基白桦酸 在 吡啶 、 氢氧化钾 、 silver(l) oxide 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 2,3,4,6-tetra-O-acetyl β-D-glucopyranosyl-3β-hydroxylup-20(29)-en-28-oate
  参考文献：
  名称：

  Synthesis of Glycosides of Lupane-Type Triterpene Acids

  摘要：

  A preparative synthesis of glucosides of the lupane-type triterpene acids betulinic, dihydrobetulinic, betulonic, dihydrobetulonic. and 3,20-dioxo-30-norlupan-28-oic was proposed. Glycosylation of 3-hydroxyacids by alpha-acetohronioglucose (ABG) with Ag2O was performed in pyridine (Py) to form glycosides at C-28, repeated glycosylation of which by these same reagents but in CH2Cl2 generated a glycoside bond at C-3 to form bisglucosides 28- Glucosides of ketoacids were formed in high yields in both Py and CH2Cl2.

  DOI：

  10.1023/b:conc.0000018113.79735.34

文献信息

• Synthesis and antiproliferative properties of new hydrophilic esters of triterpenic acids
  作者：Barbara Eignerova、Michal Tichy、Jana Krasulova、Miroslav Kvasnica、Lucie Rarova、Romana Christova、Milan Urban、Barbara Bednarczyk-Cwynar、Marian Hajduch、Jan Sarek

  DOI：10.1016/j.ejmech.2017.09.041

  日期：2017.11

  To improve the properties of cytotoxic triterpenoid acids 1–5, a large set of hydrophilic esters was synthesized. We choose betulinic acid (1), dihydrobetulinic acid (2), 21-oxoacid 3 along with highly active des-E lupane acids 4 and 5 as a model set of compounds for esterification of which the properties needed to be improved. As ester moieties were used - methoxyethanol and 2-(2-methoxyethoxy)ethanol

  为了提高细胞毒性三萜酸的性质1 - 5，一大组的亲水性酯的合成。我们选择了桦木酸（1），二氢桦木酸（2），21-含氧酸3以及高活性des-E戊烷酸4和5作为酯化化合物的模型集，其性能需要改善。作为酯部分，使用了-甲氧基乙醇和2-（2-甲氧基乙氧基）乙醇和羟基单元（a - d型），吡咯烷基乙醇，哌啶子基乙醇和吗啉代乙醇（f - h型）和单糖基团（i型-升）。结果，获得了56种三萜酸酯（49种新化合物），并测试了它们对四种癌细胞系和正常人成纤维细胞的细胞毒性。所有新化合物在所有测试浓度下均完全溶解，这曾经是母体化合物1和2的问题。 在至少一种癌细胞系中，有16种化合物的IC 50 <10μM，对四种测试的癌细胞系中的至少3种，细胞毒性<10μM。发现化合物3c的活性最高（在MCF7上为1.8μM，在HeLa上为2.8μM，在G-361细胞上为1.6μM），在最高测试浓度（50μM）下对非癌性B
• BETULINIC ACID AND DERIVATIVES THEREOF USEFUL FOR THE TREATMENT OF NEUROECTODERMAL TUMORS
  申请人：Deutsches KrebsforschungszentrumStiftung des öffentlichen Rechts

  公开号：EP1124842A1

  公开（公告）日：2001-08-22
• US6369109B1
  申请人：——

  公开号：US6369109B1

  公开（公告）日：2002-04-09
• [EN] BETULINIC ACID AND DERIVATIVES THEREOF USEFUL FOR THE TREATMENT OF NEUROECTODERMAL TUMORS<br/>[FR] ACIDE BETULINIQUE ET DERIVES DE CET ACIDE POUR LE TRAITEMENT DE TUMEURS NEUROECTODERMIQUES
  申请人：DEUTSCHES KREBSFORSCH

  公开号：WO2000024762A1

  公开（公告）日：2000-05-04

  The present invention is, generally, directed to the use of betulinic acid and derivatives thereof for the treatment of neuroectodermal tumors. The present invention is based on the discovery that betulinic acid and its deriatives are potent anti-neuroectodermal agents. As disclosed herein, betulinic acid and its derivatives are useful for the treatment of neurodectodermal tumors, including, due to its distinct mechanism of action, neuroectodermal tumors that are resistant to conventional chemotherapeutical agents. In addition to the new use of known compounds, the invention discloses novel compounds and pharmaceutical compositions for the treatment of neuroectodermal tumors.