2-hydroxy-3-oxo-ursa-1,12-dien-28-oic acid | 151071-50-0

• 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: 2-hydroxy-3-oxo-ursa-1,12-dien-28-oic acid
• 英文别名: 2-hydroxy-3-oxours-1,12-dien-28-oic acid
• CAS: 151071-50-0
• 化学式: C₃₀H₄₄O₄
• 分子量: 468.677
• InChiKey: NBZYDUVAIBSNNP-WDTJDXSOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.96
• 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：
  0.8
• 拓扑面积：
  74.6
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-hydroxy-3-oxo-ursa-1,12-dien-28-oic acid 在 盐酸 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 水 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 50.25h， 生成 N-[2β,3β-diacetyloxy-17β-amino-28-norurs-12-en-17-yl]phenylurea
  参考文献：
  名称：

  Urea derivates of ursolic, oleanolic and maslinic acid induce apoptosis and are selective cytotoxic for several human tumor cell lines

  摘要：

  2,3-Di-O-acetyl-maslinic acid benzylamide (5) has previously been shown to possess high cytotoxicity for a variety of human tumor cell lines while being of low cytotoxicity to non-malignant cells. Structural modifications performed on 5 revealed that the presence of these acetyl groups in 5 and the presence of (2 beta,3 beta)-configurated centers seems necessary for obtaining high cytotoxicity combined with best selectivity between malignant cells and non-malignant mouse fibroblasts. Compounds carrying an ursane skeleton showed weaker cytotoxicity than their oleanane derived analogs. In addition, the benzylamide function in compound 5 should be replaced by a phenylurea moiety to gain better cytotoxicity while retaining and improving the selectivity. Thus, maslinic acid derived N-[2 beta,3 beta-di-O-acetyl-17 beta-amino-28-norolean-12-en-17-yliphenylurea (45) gave best results showing EC50 = 0.9 mu M (for A2780 ovarian cancer cells) with EC50 > 120 mu M for fibroblasts (NIH 3T3) and triggered apoptosis while caspase-3 was not activated by this compound. (C) 2016 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2016.04.051
• 作为产物：
  描述：

  2-bromo-3-oxours-12-en-28-oic acid 在 sodium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以97%的产率得到2-hydroxy-3-oxo-ursa-1,12-dien-28-oic acid
  参考文献：
  名称：

  Urea derivates of ursolic, oleanolic and maslinic acid induce apoptosis and are selective cytotoxic for several human tumor cell lines

  摘要：

  2,3-Di-O-acetyl-maslinic acid benzylamide (5) has previously been shown to possess high cytotoxicity for a variety of human tumor cell lines while being of low cytotoxicity to non-malignant cells. Structural modifications performed on 5 revealed that the presence of these acetyl groups in 5 and the presence of (2 beta,3 beta)-configurated centers seems necessary for obtaining high cytotoxicity combined with best selectivity between malignant cells and non-malignant mouse fibroblasts. Compounds carrying an ursane skeleton showed weaker cytotoxicity than their oleanane derived analogs. In addition, the benzylamide function in compound 5 should be replaced by a phenylurea moiety to gain better cytotoxicity while retaining and improving the selectivity. Thus, maslinic acid derived N-[2 beta,3 beta-di-O-acetyl-17 beta-amino-28-norolean-12-en-17-yliphenylurea (45) gave best results showing EC50 = 0.9 mu M (for A2780 ovarian cancer cells) with EC50 > 120 mu M for fibroblasts (NIH 3T3) and triggered apoptosis while caspase-3 was not activated by this compound. (C) 2016 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2016.04.051

文献信息

• Discovery of triterpenoids as potent dual inhibitors of pancreatic lipase and human carboxylesterase 1
  作者：Jing Zhang、Qiu-Sha Pan、Xing-Kai Qian、Xiang-Lu Zhou、Ya-Jie Wang、Rong-Jing He、Le-Tian Wang、Yan-Ran Li、Hong Huo、Cheng-Gong Sun、Lei Sun、Li-Wei Zou、Ling Yang

  DOI：10.1080/14756366.2022.2029855

  日期：2022.12.31

  inhibitors based on PL and hCES1A hold great potential for the development of remedies for treating related metabolic diseases. In this study, a series of natural triterpenoids were collected and the inhibitory effects of these triterpenoids on PL and hCES1A were determined using fluorescence-based biochemical assays. It was found that oleanolic acid (OA) and ursolic acid (UA) have the excellent inhibitory

  摘要 胰脂肪酶（PL）是众所周知的预防和治疗肥胖的关键靶点。人羧酸酯酶1A（hCES1A）已成为治疗高脂血症的重要靶点。因此，基于 PL 和 hCES1A 的强效双靶点抑制剂的发现对于开发治疗相关代谢疾病的药物具有巨大潜力。在这项研究中，收集了一系列天然三萜类化合物，并使用基于荧光的生化测定法确定了这些三萜类化合物对 PL 和 hCES1A 的抑制作用。发现齐墩果酸（OA）和熊果酸（UA）对PL和hCES1A具有优异的抑制作用，对hCES2A具有较高的选择性。随后，合成并评估了许多基于 OA 和 UA 骨架的化合物。41 ) 对于 PL 和 hCES1A 抑制都非常重要，IC 50分别为 0.75 µM 和 0.014 µM。此外，OA 的 2-烯醇和 3-缩酮部分的化合物39对 PL 和 hCES1A 也有很强的抑制作用，IC 50分别为 2.13 µM 和 0.055 µM。此外，化合
• Synthesis and evaluation of A-seco type triterpenoids for anti-HIV-1protease activity
  作者：Ying Wei、Chao-Mei Ma、Masao Hattori

  DOI：10.1016/j.ejmech.2009.05.002

  日期：2009.10

  2,3-Seco-dioic acids derived from four different triterpene skeletons were prepared and evaluated for their anti-HIV-1 protease activity. Two A-seco derivatives showed potent inhibitory activity against HIV-1 protease (3c and 3e, IC50 5.7 and 3.9 mu M, respectively), while four other derivatives showed moderate to weak inhibition (3a, 3b, 3d and 3f, IC50 15.7-88.1 mu M). The combination of a 2,3-seco-2,3-dioic acid functional group in ring A and a free acid group at C-28 or C-30 significantly enhanced HIV-1 protease inhibitory activity (3a, 3c-3e, IC50 3.9-17.6 mu M). On the other hand, all A-seco derivatives were found to be very weak inhibitors of HCV, renin and trypsin proteases (IC50 > 80 mu M). These findings indicate that A-seco triterpenes with a carboxyl group at C-28 or C-30 are novel and highly selective HIV-1 protease inhibitors. (C) 2009 Elsevier Masson SAS. All rights reserved.