3β-propionyloxy-urs-12-en-28-oic acid | 107328-97-2

• 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: 3β-propionyloxy-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-propanoyloxy-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-4a-carboxylic acid
• CAS: 107328-97-2
• 化学式: C₃₃H₅₂O₄
• 分子量: 512.773
• InChiKey: WYUBFTSIEXMENW-XHVSEXIISA-N

物化性质

• 沸点：
  578.7±50.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.4
• 重原子数：
  37
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3β-propionyloxy-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 44.0h， 生成 N-(3-β-propionyloxy-ursane-12-ene-28-acyl)-p-bromoaniline
  参考文献：
  名称：

  A hydrophilic conjugate approach toward the design and synthesis of ursolic acid derivatives as potential antidiabetic agent

  摘要：

  在这项研究中，成功设计并合成了一系列新颖的熊果酸（UA）衍生物，通过在3-OH和/或17-COOH位置结合亲水和极性基团。

  DOI：

  10.1039/c5ra05450h
• 作为产物：
  描述：

  熊果酸 、 丙酸酐 在 吡啶 、 4-二甲氨基吡啶 作用下， 生成 3β-propionyloxy-urs-12-en-28-oic acid
  参考文献：
  名称：

  A hydrophilic conjugate approach toward the design and synthesis of ursolic acid derivatives as potential antidiabetic agent

  摘要：

  在这项研究中，成功设计并合成了一系列新颖的熊果酸（UA）衍生物，通过在3-OH和/或17-COOH位置结合亲水和极性基团。

  DOI：

  10.1039/c5ra05450h

文献信息

• 乌苏酸化学修饰物及其制备方法和应用
  申请人：广东工业大学

  公开号：CN104045678B

  公开（公告）日：2016-03-02

  本发明公开了一种乌苏酸化学修饰物及其制备方法和应用，该乌苏酸化学修饰物结构式为下式：其中：R1为酰基；R2为胺基：制备方法，乌苏酸和酸酐在催化剂条件下反应得到3β‐酰氧基‐乌苏烷型‐12‐烯‐28‐羧酸类化合物2～5；化合物2～5利用草酰氯在冰浴条件下酰化，得到3‐乙酰氧基‐乌苏烷型‐12烯‐28‐酰氯，再在缚酸剂条件下，与苯胺反应得N‐(3β‐乙酰氧基‐乌苏烷型‐12‐烯‐28‐酰)‐胺类化合物；该化合物具有抑制酶活性的作用，可应用在制备预防、控制或治疗血糖水平升高糖尿病或肥胖症的药品、饮品、食品和保健品中；属于药物合成技术领域。
• 28-(L-苯丙氨酸)-五环三萜衍生物及其合成 方法和应用
  申请人：广西师范大学

  公开号：CN109517025B

  公开（公告）日：2021-08-03

  本发明公开了一系列28‑(L‑苯丙氨酸)‑五环三萜衍生物及其合成方法和应用。所述的五环三萜衍生物具体包括2个28‑(L‑苯丙氨酸)‑齐墩果酸衍生物、2个28‑(L‑苯丙氨酸)‑熊果酸衍生物和2个28‑(L‑苯丙氨酸)‑甘草次酸衍生物。申请人的体外试验结果表明，它们对某些肿瘤细胞株具有良好的增殖抑制活性，具有较好的潜在药用价值，有望用于各种抗肿瘤药物的制备。
• Synthesis and in vitro/in vivo anticancer evaluation of pentacyclic triterpenoid derivatives linked with -phenylalanine or -proline
  作者：Yudong Yin、Lixin Sheng、Juzheng Zhang、Liqiong Zhang、Jingjing Liu、Xiaoan Wen、Yanghan Liu、Yang Si、Keguang Cheng

  DOI：10.1016/j.bioorg.2022.105865

  日期：2022.9

  Extensive research effort has been put in pentacyclic triterpenoids due to their numerous biological activities. However, their poor water solubility and low oral bioavailability limit their antitumor effects in vivo. To address these issues, 37 triterpenoid acid derivatives linked to l-phenylalanine or l-proline were designed and synthesized in this study. Structure-activity relationship (SAR) studies

  由于五环三萜类化合物具有多种生物活性，因此对其进行了广泛的研究。然而，它们的水溶性差和口服生物利用度低限制了它们在体内的抗肿瘤作用。为了解决这些问题，本研究设计并合成了37 种与l-苯丙氨酸或l-脯氨酸相连的三萜酸衍生物。构效关系 (SAR) 研究发现了两种有前景的甘草次酸 (GA) 衍生物11和16。化合物11是通过 C3-OH 酯化和用l-苯丙氨酸修饰 C30-COOH 获得的，而化合物16是通过将 C3-OH 与l连接获得的-苯丙氨酸。在细胞测定中，与天然存在的 GA的 IC 50值相比，化合物11和16分别表现出高达 48 和 120 倍的改进。荧光显微镜和流式细胞仪分析表明，化合物11和16均增加了癌细胞中 ROS 和 Ca 2+的含量，降低了线粒体膜电位（JC-1），并激活了调节因子 caspase-3/8/9 以触发细胞细胞凋亡。RNA-seq 分析和蛋白质印迹分析表明，化合
• In vitro and in vivo evaluation of the antidiabetic activity of ursolic acid derivatives
  作者：Pan-Pan Wu、Kun Zhang、Yu-Jing Lu、Ping He、Su-Qing Zhao

  DOI：10.1016/j.ejmech.2014.04.073

  日期：2014.6

  In this study, a series of ursolic acid derivatives were synthesized, and their structures were confirmed. The activity of the synthesized compounds against α-glucosidase was determined in vitro. The results suggested that all compounds have significant inhibitory activity, especially compounds 3-5 and 8, the IC50 values of which were 2.66 ± 0.84, 1.01 ± 0.44, 3.26 ± 0.22, and 3.24 ± 0.21 μM. These compounds were more potent than acarbose (positive control) against α-glucosidase. Kinetic studies were performed to determine the mechanism of inhibition by compounds 3-5 and 8. The kinetic inhibition studies indicated that compound 3 was a non-competitive inhibitor, and the inhibition constant Ki was calculated to be 2.67 ± 0.19 μM. Moreover, the kinetic inhibition studies of compounds 4, 5 and 8 demonstrated that they were mixed-type inhibitors. Furthermore, the actual pharmacological potentials of synthesized compounds 3 and 4 were demonstrated by the reduction of postprandial blood glucose levels in normal Kunming mice. The hypoglycemic effects of these compounds were more evident 30 and 60 min after maltose ingestion (P < 0.05), which was similar to the effect displayed by the positive control, acarbose.
• Ursolic acid derivatives induce cell cycle arrest and apoptosis in NTUB1 cells associated with reactive oxygen species
  作者：Huang-Yao Tu、A-Mei Huang、Bai-Luh Wei、Kim-Hong Gan、Tzyh-Chyuan Hour、Shyh-Chyun Yang、Yeong-Shiau Pu、Chun-Nan Lin

  DOI：10.1016/j.bmc.2009.08.046

  日期：2009.10

  Twenty-three ursolic acid (1) derivatives 2-24 including nine new 1 derivatives 5, 7-11, 20-22 were synthesized and evaluated for cytotoxicities against NTUB1 cells (human bladder cancer cell line). Compounds 5 and 17 with an isopropyl ester moiety at C-17-COOH and a succinyl moiety at C-3-OH showed potent inhibitory effect on growth of NTUB1 cells. Compounds 23 and 24 with seco-structures prepared from 1 also showed the increase of the cytotoxicity against NTUB1 cells. Exposure of NTUB1 to 5 (40 mu M) and 23 (20 and 50 mu M) for 24 h significantly increased the production of reactive oxygen species (ROS) while exposure of NTUB1 to 5 (20 and 40 mu M) and 23 (20 and 50 mu M) for 48 h also significantly increased the production of ROS while exposure of cells to 17 did not increase the amount of ROS. Flow cytometric analysis exhibited that treatment of NTUB1 with 5 or 17 or 23 led to the cell cycle arrest accompanied by an increase in apoptotic cell death after 24 or 48 h. These data suggest that the presentation of G1 phase arrest and apoptosis in 5- and 23-treated NTUB1 for 24 h mediated through increased amount of ROS in cells exposed with 5 and 23, respectively, while the presence of G2/M arrest before accumulation of cells in sub-G1 phase in 5-treated cells for 48 h also due to increased amount of ROS in cells exposed with 5. The inhibition of tubulin polymerization and cell cycle arrest at G2/M following by apoptosis presented in the cell cycle of 23 also mediates through the increase amount of ROS induced by treating NTUB1 with 23 for 48 h. (C) 2009 Elsevier Ltd. All rights reserved.