6-azidohexyl 3β-hydroxyolean-12-en-28-oate | 1161826-30-7

• 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: 6-azidohexyl 3β-hydroxyolean-12-en-28-oate
• 英文别名: 6-azidohexyl (4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate
• CAS: 1161826-30-7
• 化学式: C₃₆H₅₉N₃O₃
• 分子量: 581.883
• InChiKey: VTBBPCLAPMAJDR-QZUHWTNASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.1
• 重原子数：
  42
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  60.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-azidohexyl 3β-hydroxyolean-12-en-28-oate 在 水 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以68%的产率得到6-aminohexyl 3β-hydroxyolean-12-en-28-oate
  参考文献：
  名称：

  糖原磷酸化酶抑制剂C-28齐墩果酸衍生物的合成与评价

  摘要：

  已经描述了作为糖原磷酸化酶的新型抑制剂的C-28齐墩果酸衍生物的合成和评价。还讨论了糖原磷酸化酶抑制试验和结构-活性关系（SAR）分析的结果。

  DOI：

  10.2174/157018010790225921
• 作为产物：
  描述：

  齐墩果酸 在 sodium azide 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 36.0h， 生成 6-azidohexyl 3β-hydroxyolean-12-en-28-oate
  参考文献：
  名称：

  五环三萜-苯酚氮芥共轭物的合成及细胞毒性评价

  摘要：

  使用已报道的药效团、4-[N,N-双(2-氯乙基)-氨基]苯酚和五环三萜，天然产物的药理和结构多样的成分，六五环三萜-4-[N,N-bis(2 -氯乙基)-氨基]苯酚缀合物通过点击化学合成。通过 MTT 测定评估它们对 BEL-7404 和 NCI-H460 肿瘤细胞系的细胞毒性。细胞毒性试验的体外结果表明，在 20 μM 的化合物浓度下，这些偶联物对培养的受试肿瘤细胞显示出低毒性 (< 16%)。

  DOI：

  10.1007/s10600-018-2270-x

文献信息

• Synthesis and cytotoxicity of pentacyclic triterpenes‐aniline nitrogen mustard derivatives
  作者：Chun‐Mei Liu、Xiao‐Yan Tian、Chun‐Hua Su、Jia‐Yan Huang、Xiang‐Wu Chu、Sheng‐Ping Deng、Ke‐Guang Cheng

  DOI：10.1002/jccs.201900049

  日期：2020.4

  To discover novel nitrogen mustards, the reported mustard pharmacophore was combined with natural pentacyclic triterpenes, which are characterized with pharmacological and structural diversity. Thus, six conjugates were synthesized with 1,2,3‐triazole linking N,N‐bis (2‐chloroethyl)‐1,4‐phenylenediamine and oleanolic acid, ursolic acid, or glycyrrhetinic acid, and their biological activity was evaluated

  为了发现新的氮芥，将报道的芥菜药效团与天然五环三萜结合起来，其特征在于药理和结构的多样性。因此，合成了六个结合有1,2,3-三唑的N，N-双（2-氯乙基）-1,4-苯二胺和齐墩果酸，熊果酸或甘草次酸的缀合物，并评估了它们对肿瘤的生物学活性。 MTT法检测HeLa，BGC‐823，BEL‐7404和NCI‐H460细胞系。结果，这些缀合物对NCI-H460表现出一定的选择性细胞毒性，尽管它们在四种细胞系中的活性均中等或较弱。
• Synthesis of glucoconjugates of oleanolic acid as inhibitors of glycogen phosphorylase
  作者：Keguang Cheng、Jun Liu、Xiaofeng Liu、Honglin Li、Hongbin Sun、Juan Xie

  DOI：10.1016/j.carres.2009.02.012

  日期：2009.5

  Synthesis and biological evaluation of glucoconjugates of oleanolic acid, linked by either a triazole moiety or an ester function, as novel inhibitors of glycogen phosphorylase have been described. Several triterpene-glycoside conjugates exhibited moderate-to-good inhibitory activity against rabbit muscle GPa. Compound 12 showed the best inhibition with an IC(50) value of 1.14 microM. Structure-activity

  已经描述了通过三唑部分或酯官能团连接的齐墩果酸的葡萄糖缀合物的合成和生物学评估，其作为糖原磷酸化酶的新型抑制剂。几种三萜糖苷共轭物对兔肌肉GPa表现出中等至良好的抑制活性。化合物12表现出最好的抑制作用，IC（50）值为1.14 microM。还讨论了这些抑制剂的构效关系（SAR）分析。通过分子对接模拟探索了化合物12的可能结合方式。
• Synthesis of Nucleoside Conjugates as Potential Inhibitors of Glycogen Phosphorylase
  作者：Hongbin Sun、Juan Xie、Keguang Cheng、Jun Liu

  DOI：10.1055/s-0029-1218629

  日期：2010.3

  Click chemistry has been successfully used for the synthesis of novel nucleoside conjugates between uridine and N-acetylglucosamine or oleanolic acid derivatives. These molecules displayed micromolar inhibition towards glycogen phosphorylase. bioorganic chemistry - carbohydrates - click chemistry - inhibitors - nucleosides

  点击化学已成功地用于尿苷和N-乙酰氨基葡糖或齐墩果酸衍生物之间的新型核苷缀合物的合成。这些分子显示出对糖原磷酸化酶的微摩尔抑制作用。 生物有机化学-碳水化合物-点击化学-抑制剂-核苷
• Multivalent oleanolic acid human serum albumin conjugate as nonglycosylated neomucin for influenza virus capture and entry inhibition
  作者：Yang Yang、Hao-Jie He、Hao Chang、Yao Yu、Mei-Bing Yang、Yun He、Zhen-Chuan Fan、Suri S. Iyer、Peng Yu

  DOI：10.1016/j.ejmech.2017.10.070

  日期：2018.1

  We report the synthesis of multivalent oleanolic acid (OA) protein conjugates as nonglycosylated neomucin mimic for the capture and entry inhibition of influenza viruses. Oleanolic acid derivatives bearing an amine-terminated linker were synthesized by esterification of carboxylic acid and further grafted onto the human serum albumin (HSA) via diethyl squarate method. The binding of hemagglutinin (HA) on the virion surface to the synthetic neomucin was evaluated by hemagglutination inhibition assay. The influenza virus capture ability of the PEGylated OA-HSA conjugate was further investigated by Dynamic Light Scattering (DLS), virus capture assay and Isothermal Titration Calorimeter (ITC) techniques. The pronounced agglutination of viral particles, the high capture efficiency and affinity constant indicate that this neoprotein is comparable to natural glycosylated mucin, suggesting that this material could potentially be used as anti-infective barriers to prevent virus from invading host cells. The study also rationalizes the feasibility of antiviral drug development based on OA or other antiviral small molecules conjugated protein strategies. (C) 2017 Elsevier Masson SAS. All rights reserved.