isopropyl (1S,2R,4aS,6aS,6bR,8aR,10S,12aR,12bR,14bS)-10-hydroxy-1,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-octadecahydropicene-4a(2H)-carboxylate | 1198208-24-0

• 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: isopropyl (1S,2R,4aS,6aS,6bR,8aR,10S,12aR,12bR,14bS)-10-hydroxy-1,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-octadecahydropicene-4a(2H)-carboxylate
• 英文别名: isopropyl 3β-hydroxyurs-12-en-28-oate；isopropyl 3β-hydroxyurs-12-en-28-oat；UA17；propan-2-yl (1S,2R,4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-hydroxy-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-4a-carboxylate
• CAS: 1198208-24-0
• 化学式: C₃₃H₅₄O₃
• 分子量: 498.79
• InChiKey: QVUVIIRQMJBPQM-ABODYXKQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.5
• 重原子数：
  36
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-碘代丙烷 、 熊果酸 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 以90%的产率得到isopropyl (1S,2R,4aS,6aS,6bR,8aR,10S,12aR,12bR,14bS)-10-hydroxy-1,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-octadecahydropicene-4a(2H)-carboxylate
  参考文献：
  名称：

  URSOLIC ACID DERIVATIVE AND PHARMACEUTICAL COMPOSITION THEREOF

  摘要：

  提供了几种熊果酸衍生物及其药物组合物。这些熊果酸衍生物和药物组合物具有抗癌和抗炎作用中的至少一种。还提供了一种增加细胞中活性氧自由基的方法。该方法包括向细胞提供包含熊果酸衍生物的药物组合物的步骤。

  公开号：

  US20110190388A1

文献信息

• Modulators of ROR-gamma Receptors, Composition and Use Thereof
  申请人：KULING THERAPEUTICS

  公开号：US20170298090A1

  公开（公告）日：2017-10-19

  The present invention provides novel methods to treat disease by modulating retinoid-related orphan receptor gamma (ROR-gamma) in vitro and in vivo with ursolic acid analogs, and compositions thereof. The methods and compounds disclosed herein are useful for inhibiting the differentiation of a population of T cells, or treating a disease related to Th17 cell responses in a subject. Examples of such diseases include, but are not limited to, autoimmune diseases, multiple sclerosis, rheumatoid arthritis, psoriasis and diabetes.

  本发明提供了一种通过使用熊果酸类似物在体外和体内调节视黄醇相关孤儿受体γ（ROR-gamma）来治疗疾病的新方法，以及相关组合物。本文披露的方法和化合物对于抑制T细胞群体的分化或治疗与Th17细胞反应相关的疾病非常有用。此类疾病的示例包括但不限于自身免疫疾病、多发性硬化症、类风湿性关节炎、牛皮癣和糖尿病。
• 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.
• US8729055B2
  申请人：——

  公开号：US8729055B2

  公开（公告）日：2014-05-20
• URSOLIC ACID DERIVATIVE AND PHARMACEUTICAL COMPOSITION THEREOF
  申请人：Lin Chun-Nan

  公开号：US20110190388A1

  公开（公告）日：2011-08-04

  Several ursolic acid derivatives and pharmaceutical compositions thereof are provided. The ursolic acid derivatives and the pharmaceutical compositions thereof have at least one of an anticancer and an anti-inflammatory effects. A method for increasing a reactive oxygen species in a cell is also provided. The method comprises a step of providing the cell with a pharmaceutical composition including an ursolic acid derivative.

  提供了几种熊果酸衍生物及其药物组合物。这些熊果酸衍生物和药物组合物具有抗癌和抗炎作用中的至少一种。还提供了一种增加细胞中活性氧自由基的方法。该方法包括向细胞提供包含熊果酸衍生物的药物组合物的步骤。