3-hydroxyimino-urs-12-en-28-oic acid | 72808-18-5

• 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-hydroxyimino-urs-12-en-28-oic acid
• 英文别名: (1S,2R,4aS,6aR,6aS,6bR,8aR,12aR,14bS)-10-hydroxyimino-1,2,6a,6b,9,9,12a-heptamethyl-1,2,3,4,5,6,6a,7,8,8a,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
• CAS: 72808-18-5
• 化学式: C₃₀H₄₇NO₃
• 分子量: 469.708
• InChiKey: FMHWMOZSBSUIPO-OADIDDRXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  34
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  69.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-hydroxyimino-urs-12-en-28-oic acid 在 吡啶 、 4-二甲氨基吡啶 、 草酰氯 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 20.08h， 生成 3-acetoxyimineursolic acid morpholine amide
  参考文献：
  名称：

  Synthesis and antitumor activity evaluation of novel ursolic acid derivatives

  摘要：

  Eleven novel ursolic acid (UA) derivatives were designed and synthesized with modification at positions of C-2, C-3, and C-28 of UA. Their structures were confirmed by MS, H-1 NMR, and elemental analysis. Their in vitro cytotoxicities against various cancer cell lines (HeLa, HepG2, and BGC-823) were evaluated by MTT assay. The results indicated that all compounds could inhibit cell proliferation of HeLa, HepG2, and BGC-823 cells. Among them, compounds I-3 and I-4 showed more potent cytotoxicity on these three tumor cells than gefitinib (positive control), worthy to be studied further.

  DOI：

  10.1080/10286020.2015.1070830
• 作为产物：
  描述：

  熊果酸 在 吡啶 、 盐酸羟胺 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 4.0h， 生成 3-hydroxyimino-urs-12-en-28-oic acid
  参考文献：
  名称：

  Hyaluronidase Inhibitory Activity of Pentacylic Triterpenoids from Prismatomeris tetrandra (Roxb.) K. Schum: Isolation, Synthesis and QSAR Study

  摘要：

  哺乳动物透明质酸酶通过裂解 β-1,4-糖苷键来降解透明质酸，提供四糖分子作为主要产物，四糖分子是高度血管生成和炎性细胞因子的有效诱导剂。熊果酸 1 是从 Prismatomeris tetrandra 中分离出来的，被鉴定为具有开发透明质酸酶抑制剂的潜力。通过熊果酸1的结构修饰合成了一系列熊果酸类似物，或者通过商业途径获得。评价这些化合物对透明质酸酶的抑制活性。使用半经验量子化学方法计算了这些化合物的几种结构、拓扑和量子化学描述符。进行定量结构活性关系研究 (QSAR)，将这些描述符与透明质酸酶抑制活性相关联。最佳多线性模型（BML）（R2 = 0.9717，R2cv = 0.9506）提供的统计特征表明所开发模型具有令人满意的稳定性和预测能力。用于确定结合相互作用的计算机分子对接研究表明，熊果酸类似物22对人透明质酸酶具有很强的亲和力。

  DOI：

  10.3390/ijms17020143

文献信息

• Synthesis and Cytotoxic Activity of Ursolic Acid Derivatives
  作者：Dao Duc Thien、Nguyen Thanh Tam、Dinh Gia Thien、Nguyen Thi Hoang Anh、Tran Van Sung

  DOI：10.5560/znb.2013-2261

  日期：2013.2.1

  Fourteen ursolic acid derivatives, among them four novel compounds, were synthesized by modification either at the C-3, C-28 or both positions. The cytotoxic activity of the obtained derivatives was evaluated against the four human cancer cell lines KB (human mouth epidermal carcinoma), HepG2 (human hepatocellular carcinoma), MCF7 (human breast carcinoma) and Lu (human lung carcinoma). As the result, compounds 7and 8were from two to three times more active than ursolic acid on all four tested cell lines. This is the first report on cytotoxic effects of the synthetized ursolic acid derivatives 4, 8, and .

  10-15 通过对 C-3、C-28 或两个位置进行修饰，合成了 14 种熊果酸衍生物，其中包括 4 种新型化合物。评估了所获衍生物对 KB（人口腔表皮癌）、HepG2（人肝癌）、MCF7（人乳腺癌）和 Lu（人肺癌）四种人癌细胞系的细胞毒活性。结果表明，化合物 7 和 8 对所有四种测试细胞株的活性是熊果酸的两到三倍。这是首次报道合成的熊果酸衍生物 4、8 和 。
• The Beckmann Rearrangement Applied to Ursolic Acid with Antimalarial Activity in Medicinal Chemistry Studies
  作者：Luciana Dalla-Vechia、Alexandra Dassonville-Klimpt、Philippe Grellier、Pascal Sonnet、Grace Gosmann、Simone C.B. Gnoatto

  DOI：10.2174/157017812800221708

  日期：2012.2.1

  The A ring-expanded derivative of ursolic acid and the corresponding fragmentation product were obtained through the Beckmann rearrangement under optimized reaction conditions. A mechanistic approach was taken in order to explain both the specificity of the rearrangement and the fragmentation of the cycle. The intermediates and the final products of the route were evaluated for antimalarial activity.

  在优化的反应条件下，通过贝克曼重排获得了熊果酸的 A 环扩展衍生物和相应的破碎产物。为了解释重排和循环破碎的特异性，我们采用了一种机理方法。对该路线的中间产物和最终产物进行了抗疟活性评估。
• Synthesis of 3-deoxy-3β-(3-aminopropoxyamino) derivatives of oleanolic and ursolic acids
  作者：G. V. Giniyatullina、O. B. Kazakova、G. A. Tolstikov

  DOI：10.1007/s10600-010-9734-y

  日期：2010.11

  3-Deoxy-3β-(3-aminopropoxyamino) derivatives of oleanolic and ursolic acids were synthesized. 3-Deoxy3-(2-cyanoethoxyimino)urs-12-en-28-oic acid was active in vitro with selectivity index SI 30 against papilloma virus (strain HPV-11).

  合成了齐墩果酸和熊果酸的3-脱氧-3β-(3-氨基丙氧基氨基)衍生物。 3-Deoxy3-(2-cyanoethoxyimino)urs-12-en-28-oic 酸在体外具有针对乳头状瘤病毒（HPV-11 株）的选择性指数 SI 30 的活性。
• Design, synthesis and biological evaluation of fluorescent derivatives of ursolic acid in living cells
  作者：Wenyi Mei、Lijuan Xie、Xiaodong Zhang、Cunjian Shi、Fengzhi Wang、Qiqi Fu、Zhenjiang Zhao、Honglin Li、Yufang Xu、Zhuo Chen

  DOI：10.1016/j.cclet.2023.108825

  日期：2024.5

  Ursolic acid (UA) is a naturally occurring ursane triterpenoid, which exhibits a wide range of unique biological activities. To clarify its mechanism of action (MOA), a series of fluorescent derivatives of UA (–) were designed and synthesized by conjugation with 7-nitrobenzo-2-oxa-1,3-diazole (NBD) fluorophore. Among them, exhibited similar anti-proliferative activity with UA against HCT116 cells (half

  熊果酸（UA）是一种天然存在的熊果三萜类化合物，具有多种独特的生物活性。为了阐明其作用机制（MOA），通过与7-硝基苯并-2-氧杂-1,3-二唑（NBD）荧光团缀合设计并合成了一系列UA（–）荧光衍生物。其中，对HCT116细胞表现出与UA相似的抗增殖活性（半数抑制浓度（IC）= 9.21 ± 0.50 µmol/L）。细胞成像实验表明，HCT116 细胞以剂量和时间依赖性方式快速吸收。然后，通过共聚焦显微镜研究发现，它定位于内质网 (ER)、溶酶体和线粒体，但不定位于 HCT116 细胞的细胞核中。初步MOA证明UA通过独特的细胞内分布机制（涉及ER和溶酶体）诱导自噬。总之，我们的工作为揭示UA作为抗肿瘤药物的分子机制提供了新的线索。
• The cytotoxic activity of ursolic acid derivatives
  作者：Chao-Mei Ma、Shao-Qing Cai、Jing-Rong Cui、Rui-Qing Wang、Peng-Fei Tu、Masao Hattori、Mohsen Daneshtalab

  DOI：10.1016/j.ejmech.2005.01.001

  日期：2005.6

  Ursolic acid and 2a-hydroxyursolic acid isolated from apple peels were found to show growth inhibitory activity against four tumor cell lines, HL-60, BGC, Bel-7402 and Hela. Structural modifications were performed on the C-3, C-28 and C-11 positions of ursolic acid and the cytotoxicity of the derivatives was evaluated. The SAR revealed that the triterpenes possessing two hydrogen-bond forming groups (an H-donor and a carbonyl group) at positions 3 and 28 exhibit cytotoxic activity. The configuration at C-3 was found to be important for the activity. Introduction of an amino group increased the cytotoxicity greatly. A 3 beta-amino derivative was 20 times more potent than the parent ursolic acid. The 28-aminoalkyl dimer compounds showed selective cytotoxicity. (c) 2005 Elsevier SAS. All rights reserved.