3,11-dioxo-olean-12-en-30-oyl chloride | 52491-48-2

• 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: 3,11-dioxo-olean-12-en-30-oyl chloride
• 英文别名: 3,11-Dioxo-olean-12-en-30-oylchlorid
• CAS: 52491-48-2
• 化学式: C₃₀H₄₃ClO₃
• 分子量: 487.123
• InChiKey: DVVRYLCMKKPMHM-LPXJIFNVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  34.0
• 可旋转键数：
  1.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  51.21
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3,11-dioxo-olean-12-en-30-oyl chloride 在 palladium 10% on activated carbon 、 氢气 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 12.5h， 生成
  参考文献：
  名称：

  细胞毒性和抗血管生成三萜类化合物-Jacaranone缀合物的合成及生物学评价

  摘要：

  背景：抗血管生成剂的开发作为一种更有效和选择性的癌症治疗方法而出现。除减少急性毒性外，将特定的抗血管生成剂与细胞毒性剂联合使用时，化疗的功效可能得到改善。双功能分子的缀合或杂交是抗癌药共同给药的另一种合理设计策略。 目的和方法：这项工作的目的是制备抗血管生成的三萜，3-氧代齐墩果酸和与结构相关的三萜与细胞毒性的半苯醌，j草酮的结合物。测定了片段和缀合物的细胞毒性，抗增殖和抗血管生成活性。使用相似性整合方法（SEA）预测了缀合物6a-6h的可能目标。 结果：结果表明，这些缀合物在细胞毒性和抗血管生成测定中均比其相应的亲本分子更有效，并且比其他两个癌细胞系（A549和MCF-7）对黑素瘤细胞B16和转移性B16BL6的选择性活性更高经过测试。预计的抗血管生成相关靶标可能涉及糖原磷酸化酶，神经氨酸酶，干扰素γ和微管蛋白β链。 结论：双功能偶联物可用作双重作用的抗肿瘤/抗血管生成剂。

  DOI：

  10.2174/1573406412666160502153930
• 作为产物：
  描述：

  甘草次酸 在 草酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 3,11-dioxo-olean-12-en-30-oyl chloride
  参考文献：
  名称：

  细胞毒性和抗血管生成三萜类化合物-Jacaranone缀合物的合成及生物学评价

  摘要：

  背景：抗血管生成剂的开发作为一种更有效和选择性的癌症治疗方法而出现。除减少急性毒性外，将特定的抗血管生成剂与细胞毒性剂联合使用时，化疗的功效可能得到改善。双功能分子的缀合或杂交是抗癌药共同给药的另一种合理设计策略。 目的和方法：这项工作的目的是制备抗血管生成的三萜，3-氧代齐墩果酸和与结构相关的三萜与细胞毒性的半苯醌，j草酮的结合物。测定了片段和缀合物的细胞毒性，抗增殖和抗血管生成活性。使用相似性整合方法（SEA）预测了缀合物6a-6h的可能目标。 结果：结果表明，这些缀合物在细胞毒性和抗血管生成测定中均比其相应的亲本分子更有效，并且比其他两个癌细胞系（A549和MCF-7）对黑素瘤细胞B16和转移性B16BL6的选择性活性更高经过测试。预计的抗血管生成相关靶标可能涉及糖原磷酸化酶，神经氨酸酶，干扰素γ和微管蛋白β链。 结论：双功能偶联物可用作双重作用的抗肿瘤/抗血管生成剂。

  DOI：

  10.2174/1573406412666160502153930

文献信息

• Structurally modified glycyrrhetinic acid derivatives as anti-inflammatory agents
  作者：Ming Bian、Dong Zhen、Qing-Kun Shen、Huan-Huan Du、Qian-Qian Ma、Zhe-Shan Quan

  DOI：10.1016/j.bioorg.2020.104598

  日期：2021.2

  With the aim of finding new anti-inflammatory drugs, a series of new Glycyrrhetinic acid derivatives (1–34) have been designed and synthesized by structural modification, and their anti-inflammatory activities in vitro have been evaluated. The anti-inflammatory activities assay demonstrated that compound 5b suppressed the expression of pro-inflammatory cytokines including IL-6, TNF-α and NO, it also

  以寻找新型抗炎药为目的，通过结构修饰设计合成了一系列新的甘草次酸衍生物（1-34），并对其体外抗炎活性进行了评价。抗炎活性测定表明，化合物 5b 抑制了促炎细胞因子包括 IL-6、TNF-α 和 NO 的表达，它还抑制了 LPS 诱导的 RAW264.7 细胞中 iNOS 和 COX-2 的表达。剂量依赖性方式。此外，蛋白质印迹结果表明化合物 5b 对促炎细胞因子的抑制作用与抑制 NF-κB 和 MAPK 信号通路有关。
• α-Glucosidase and cholinesterase inhibiting potential of a series of semisynthetic nitrogen triterpenic derivatives
  作者：Oxana Kazakova、Irina Smirnova、Ha Thi Thu Nguyen、Niels V. Heise、Sophie Hoenke、Immo Serbian、René Csuk

  DOI：10.1007/s00044-023-03014-0

  日期：2023.3

  In this study, a series of 40 semisynthetic nitrogen triterpenic derivatives of lupane, oleanane and ursane type including 33 previously synthesized and 7 new compounds were synthesized and screened to determine their ability to act as inhibitors for the enzymes α-glucosidase (from S. saccharomyces), acetylcholinesterase (AChE, from electric eel) and butyrylcholinesterase (BChE, from equine serum)

  在这项研究中，合成并筛选了一系列 40 种羽扇烷、齐墩果烷和熊烷类型的半合成氮三萜衍生物，包括 33 种先前合成的化合物和 7 种新化合物，以确定它们作为酶α-葡萄糖苷酶（来自S. saccharomyces )、乙酰胆碱酯酶（AChE，来自电鳗）和丁酰胆碱酯酶（BChE，来自马血清）。结果，40 种化合物中有 17 种表现出对α-葡萄糖苷酶的显着抑制特性，IC 50值不超过 10 μM，阿卡波糖的 IC 50为 178.25 μM 作为参考。A-azepano-28-cinnamoyloxy-erythrodiol 被发现是一种先导化合物，IC为 50值为 0.22 μM，因此活性是阿卡波糖的 810 倍。化合物6和15是酶 AChE 的中等抑制剂，但对 BChE 的活性较低，羽扇豆型偕胺肟11表现出较高的活性，对 AChE 的抑制率为 41.98%，而熊磺酸N-乙基-哌嗪基-酰胺34是
• Synthesis of novel 3-amino and 29-hydroxamic acid derivatives of glycyrrhetinic acid as selective 11β-hydroxysteroid dehydrogenase 2 inhibitors
  作者：Christian Stanetty、Laszlo Czollner、Iris Koller、Priti Shah、Rawindra Gaware、Thierry Da Cunha、Alex Odermatt、Ulrich Jordis、Paul Kosma、Dirk Claßen-Houben

  DOI：10.1016/j.bmc.2010.08.046

  日期：2010.11

  Glycyrrhetinic acid, the metabolite of the natural product glycyrrhizin, is a well known nonselective inhibitor of 11 beta-hydroxysteroid dehydrogenase (11 beta-HSD) type 1 and type 2. Whereas inhibition of 11 beta-HSD1 is currently under consideration for treatment of metabolic diseases, such as obesity and diabetes, 11 beta-HSD2 inhibitors may find therapeutic applications in chronic inflammatory diseases and certain forms of cancer. So far, no selective 11 beta-HSD2 inhibitor has been developed and neither animal studies nor clinical trials have been reported based on 11 beta-HSD2 inhibition. Starting from the lead compound glycyrrhetinic acid, novel triterpene type derivatives were synthesized and analyzed for their biological activity against overexpressed human 11 beta-HSD1 and 11 beta-HSD2 in cell lysates. Several hydroxamic acid derivatives showed high selectivity for 11 beta-HSD2. The most potent and selective compound is active against human 11 beta-HSD2 in the low nanomolar range with a 350-fold selectivity over human 11 beta-HSD1. (C) 2010 Elsevier Ltd. All rights reserved.
• Conjugates of 18β-glycyrrhetinic acid derivatives with 3-(1H-benzo[d]imidazol-2-yl)propanoic acid as Pin1 inhibitors displaying anti-prostate cancer ability
  作者：Kun Li、Tianyi Ma、Jingjing Cai、Min Huang、Hongye Guo、Di Zhou、Shenglin Luan、Jinyu Yang、Dan Liu、Yongkui Jing、Linxiang Zhao

  DOI：10.1016/j.bmc.2017.08.002

  日期：2017.10

  Twenty-six conjugates of 18 beta-glycyrrhetinic acid derivatives with 3-(1H-benzo[d]imidazol-2-yl)propanoic acid were designed and synthesized as Pin1 inhibitors. Most of these semi-synthetic compounds showed improved Pin1 inhibitory activity and anti-proliferative effects against prostate cancer cells as compared to 3-(1H-benzo[d] imidazol-2-yl) propanoic acid and GA. Compounds 10a and 12i were the most potent to inhibit growth of prostate cancer PC-3 with GI(50) values of 7.80 mu M and 3.52 mu M, respectively. The enzyme inhibition ratio of nine compounds at 10 mu M was over 90%. Structure-activity relationships indicated that both appropriate structure at ring C of GA and suitable length of linker between GA skeleton and benzimidazole moiety had significant impact on improving activity. Western blot assay revealed that 10a decreased the level of cell cycle regulating protein cyclin D1. Thus, these compounds might represent a novel anti-proliferative agent working through Pin1 inhibition. (C) 2017 Published by Elsevier Ltd.