3β-[(pyridine-3-carbonyl)oxy]urs-12-en-28-oic acid | 1262661-03-9

• 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-[(pyridine-3-carbonyl)oxy]urs-12-en-28-oic acid
• 英文别名: (1S,2R,4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-1,2,6a,6b,9,9,12a-heptamethyl-10-(pyridine-3-carbonyloxy)-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-4a-carboxylic acid
• CAS: 1262661-03-9
• 化学式: C₃₆H₅₁NO₄
• 分子量: 561.805
• InChiKey: IGMCMEFRZDLZJF-WMHNVREMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.35
• 重原子数：
  41.0
• 可旋转键数：
  3.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  76.49
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  熊果酸 在 4-二甲氨基吡啶 、 palladium 10% on activated carbon 、 氢气 、 potassium carbonate 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 28.0h， 生成 3β-[(pyridine-3-carbonyl)oxy]urs-12-en-28-oic acid
  参考文献：
  名称：

  Synthesis, biological evaluation and SAR studies of ursolic acid 3β-ester derivatives as novel CETP inhibitors

  摘要：

  Cholesteryl ester transfer protein (CETP) is an attractive therapeutic target for the prevention and treatment of cardiovascular diseases by lowering low-density lipoprotein cholesterol levels as well as raising high-density lipoprotein cholesterol levels in human plasma. Herein, a series of ursolic acid 3 beta-ester derivatives were designed, synthesized and evaluated for the CETP inhibiting activities. Among these compounds, the most active compound is U12 with an IC50 value of 2.4 mu M in enzymatic assay. The docking studies showed that the possible hydrogen bond interactions between the carboxyl groups at both ends of the molecule skeleton and several polar residues (such as Ser191, Cys13 and Ser230) in the active site region of CETP could significantly enhance the inhibition activity. This study provides structural insight of the interactions between these pentacyclic tri-terpenoid 3 beta-ester derivatives and CETP protein for the further modification and optimization.

  DOI：

  10.1016/j.bmcl.2019.126824

文献信息

• Synthesis of triterpenoid acylates: Effective reproduction inhibitors of influenza A (H1N1) and papilloma viruses
  作者：O. B. Kazakova、N. I. Medvedeva、I. P. Baikova、G. A. Tolstikov、T. V. Lopatina、M. S. Yunusov、L. Zaprutko

  DOI：10.1134/s1068162010060142

  日期：2010.11

  The synthesis of a new group of triterpenoid acylates has been conducted on the basis of oleanolic, glycyrrhetic, and ursolic acids and betulin. 28-ortho-Methoxycynnamoylbetulin has been demonstrated to possess high activity against the influenza type A (H1N1) virus with the selectivity index SI > 100 while studying the activity of the synthesized compounds in relation to the reproduction of viral

  以齐墩果酸、甘草次酸、熊果酸和桦木脑为基础合成了一组新的三萜酰化物。在研究合成化合物与呼吸道感染病毒病原体繁殖相关的活性时，28-ortho-Methoxycynnamoylbetulin 已被证明对甲型流感 (H1N1) 病毒具有高活性，选择性指数 SI > 100。3,28-二烟酰桦木素对乳头状瘤病毒（HPV-11 株）具有高活性，选择性指数 SI 35。
• Synthesis and Antimicrobial Activity of Ursolic Acid Ester Derivatives
  作者：Vinicius Viana Pereira、Nara Rúbia Pereira、Rafael César Gonçalves Pereira、Lucienir Pains Duarte、Jacqueline Aparecida Takahashi、Roqueline Rodrigues Silva

  DOI：10.1002/cbdv.202100566

  日期：2022.1

  antimicrobial agents. Ursolic acid is a triterpene with known antibacterial action, being naturally found in plants, such as Jaracanda oxyphylla and Jacaranda caroba (Bignoniaceae). Ursolic acid derivative esters have revealed potential biological activities, such as antitumor, antiviral, and antibacterial activity. In this study, sixteen esters (1-16) were synthesized from ursolic acid using DIC/DMAP and characterized

  微生物引起的感染是全世界发病和死亡的主要原因，天然产物仍然是发现新抗菌剂的重要来源。熊果酸是一种具有已知抗菌作用的三萜，天然存在于植物中，例如Jaracanda oxyphylla和Jacaranda caroba （紫葳科）。熊果酸衍生物酯已显示出潜在的生物活性，例如抗肿瘤、抗病毒和抗菌活性。在本研究中，使用 DIC/DMAP 从熊果酸合成了 16 种酯 ( 1 - 16 )，并通过红外 (IR)、核磁共振 ( 1 H- 和13 C-NMR) 和质谱进行了表征。所有熊果酸酯均针对蜡样芽孢杆菌、金黄色葡萄球菌、大肠杆菌、鼠伤寒沙门氏菌和白色念珠菌进行了评估。 6种化合物（ 3、9、11、13、14和16 ）为首次描述，收率高达91.6 %。化合物11 （ 3β- （3,4-二甲氧基苯甲酰基）熊果酸）和15 （ 3β-烟酰熊果酸）显示出良好的抗真菌活性，对白色念珠菌生长的抑制率分别为93.1%和95