2α,3β,23-triacetoxy-11-oxo-urs-12-en-28-oic acid

• 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: 2α,3β,23-triacetoxy-11-oxo-urs-12-en-28-oic acid
• 英文别名: 2α,3β,23-triacetoxyurs-11-oxo-12-ene-28-oic acid；11-oxoasiatic acid triacetate；2α,3β,23-Triacetoxy-11-oxo-urs-12-en-28-saeure；(1S,2R,4aS,6aR,6aS,6bR,8aR,9R,10R,11R,12aS,14bS)-10,11-diacetyloxy-9-(acetyloxymethyl)-1,2,6a,6b,9,12a-hexamethyl-13-oxo-1,2,3,4,5,6,6a,7,8,8a,10,11,12,14b-tetradecahydropicene-4a-carboxylic acid
• 化学式: C₃₆H₅₂O₉
• 分子量: 628.803
• InChiKey: KSHAUYAIHPXNEN-RRHKSWSFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  45
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  133
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2α,3β,23-triacetoxy-11-oxo-urs-12-en-28-oic acid 在 草酰氯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 N-[2α,3β,23-triacetoxyurs-11-oxo-12-ene-28-oyl]diethylamine
  参考文献：
  名称：

  Synthesis and antitumor activity evaluation of new asiatic acid derivatives

  摘要：

  Twelve novel asiatic acid (AA) derivatives were designed and synthesized. Their structures were confirmed using NMR, MS, and IR spectra. Their in vitro cytotoxicities on various cancer cell lines (HeLa, HepG2, BGC-823, and SKOV3) were evaluated by the 3-(4,5-dimethyl-2-thiazolyl)-2,5-diphenyl-2H-tetrazolium bromide assay. Most of the derivatives were found to have stronger cell growth inhibitory activity than AA. Among them, compounds 5-8 and 11 with substituted amide group at C-28 exhibited more potent cytotoxicity than AA, Gefitinib, and etoposide (positive control).

  DOI：

  10.1080/10286020.2012.699961
• 作为产物：
  描述：

  积雪草苷 在 吡啶 、 甲醇 、 Cr₂O₇^(2-)*2K⁽¹⁺⁾*2H₂O 、 溶剂黄146 、 sodium hydroxide 作用下， 反应 13.0h， 生成 2α,3β,23-triacetoxy-11-oxo-urs-12-en-28-oic acid
  参考文献：
  名称：

  含有[小α]-氨基膦酸酯的新型积雪草酸衍生物的合成，抗增殖和诱导细胞凋亡的作用

  摘要：

  这是已接受的手稿，已通过RSC出版同行评审过程，并已被接受出版。接受的手稿在接受后不久就会在线发布。一旦可用，此版本的文章将被完全编辑，格式化并提供高级阅读的高级文章代替。

  DOI：

  10.1039/c6ra11397d

文献信息

• Synthesis and discovery of asiatic acid based 1,2,3-triazole derivatives as antitumor agents blocking NF-κB activation and cell migration
  作者：Ri-Zhen Huang、Gui-Bin Liang、Mei-Shan Li、Yi-Lin Fang、Shi-Feng Zhao、Mei-Mei Zhou、Zhi-Xin Liao、Jing Sun、Heng-Shan Wang

  DOI：10.1039/c8md00620b

  日期：——

  A series of asiatic acid (AA) based 1,2,3-triazole derivatives were designed, synthesized and subjected to a cell-based NF-κB inhibition screening assay. Among the tested compounds, compound 6k displayed impressive NF-κB inhibitory activity with an IC50 value in the low micromolar range. A molecular docking study was performed to reveal key interactions between 6k and NF-κB in which the 1,2,3-triazole

  设计、合成了一系列基于积雪草酸 (AA) 的 1,2,3-三唑衍生物，并对其进行了基于细胞的 NF-κB 抑制筛选试验。在测试的化合物中，化合物 6k 显示出令人印象深刻的 NF-κB 抑制活性，IC50 值在低微摩尔范围内。进行分子对接研究以揭示 6k 和 NF-κB 之间的关键相互作用，其中 1,2,3-三唑部分和 AA 骨架的羟基对提高抑制活性很重要。随后，表面等离子共振分析验证了化合物 6k 与 NF-κB 蛋白之间的高亲和力，平衡解离常数 (KD) 值为 0.36 μM。进一步的研究表明，化合物 6k 显着抑制了 NF-κB DNA 结合、核转位和 IκBα 磷酸化。而且，体外抗肿瘤活性筛选显示，化合物 6k (IC50 = 2.67 ± 0.06 μM) 对 A549 细胞表现出最好的抗癌活性，至少部分是通过抑制 NF-κB 的活性。此外，用化合物 6k 处理 A549 细胞导
• Synthesis and antitumor activity evaluation of asiatic acid derivatives as survivin inhibitor
  作者：Yan-Qiu Meng、Hua-Bo Cui、Lei Li、Wei-Chen Zhang、Hong-Shuang Pan、Ting-Ting Yu、Wei Li

  DOI：10.1080/10286020.2017.1405940

  日期：2018.9.2

  A series of asiatic acid derivatives were synthesized and their cytotoxicities in vitro against two cancer cell lines (HepG2 and SGC7901) were evaluated by MTT assay. The results showed that compounds I2, I6, and II6 have more potent anticancer activity than that of the positive control drug paclitaxel. The interactions between the compounds I2, I6, and II6 and survivin were also studied by docking

  合成了一系列的积雪草酸衍生物，并通过MTT法评估了它们对两种癌细胞系（HepG2和SGC7901）的体外细胞毒性。结果表明，与阳性对照药物紫杉醇相比，化合物I 2，I 6和II 6具有更强的抗癌活性。还通过对接模拟研究了化合物I 2，I 6和II 6与survivin之间的相互作用。
• 一种具有抗肿瘤活性积雪草酸化学修饰物及其制备方法
  申请人：沈阳化工大学

  公开号：CN114524858A

  公开（公告）日：2022-05-24

  一种具有抗肿瘤活性的积雪草酸化学修饰物及其制备方法，涉及一种天然产物积雪草酸的结构改造物及其制备方法，该方法通过对积雪草酸进行化学修饰，得到一系列具有生物活性的结构类似物。经药理实验证明，该积雪草酸结构类似物对人宫颈癌细胞（Hela），人肝癌细胞（HepG2），人胃癌细胞（BGC‑823，SGC‑7901）和人肺癌细胞（A549）具有较好的抑制作用，且优于母体化合物积雪草酸。所述积雪草酸结构类似物包括以下四类。
• Synthesis and biological evaluation of novel aniline-derived asiatic acid derivatives as potential anticancer agents
  作者：Jian-Fei Li、Ri-Zhen Huang、Gui-Yang Yao、Man-Yi Ye、Heng-Shan Wang、Ying-Ming Pan、Jing-Teng Xiao

  DOI：10.1016/j.ejmech.2014.08.003

  日期：2014.10

  Asiatic acid (AA) derivatives 4 and 5 modified at the C-11 and C-28 positions were designed and synthesized, their structures were confirmed using HRMS, (1)H NMR and (13)C NMR. In vitro antitumor activities of all compounds against MGC-803, NCI-H460, HepG2, Hela and 7404 cancer cell lines were evaluated and compared with commercial anticancer drug 5-fluorouracil (5-FU), employing standard MTT assay. The new compounds 5a-5t showed stronger anti-proliferative activity than AA, especially compound 5b was found to be the best inhibition activity on HepG2 cell line. In addition, the mechanism of compound 5b was preliminarily investigated by acridine orange/ethidium bromide staining, Hoechst 33258 staining, JC-1 mitochondrial membrane potential staining, flow cytometric, qRT-PCR (quantitative real-time PCR) and Western blot. Compound 5b induced the productions of ROS, and altered anti- and pro-apoptotic proteins, leading to mitochondrial dysfunction and activations of caspase-9 and caspase-3 for causing cell apoptosis. Moreover, the cell cycle analysis showed that compound 5b mainly arrested HepG2 cells in G1 stage.
• Polonsky, Bulletin de la Societe Chimique de France, 1952, p. 649,1015
  作者：Polonsky

  DOI：——

  日期：——