3,11-dioxours-12-en-28-oic acid | 73047-75-3

• 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: 3,11-dioxours-12-en-28-oic acid
• 英文别名: (1S,2R,4aS,6aR,6aS,6bR,8aR,12aS,14bS)-1,2,6a,6b,9,9,12a-heptamethyl-10,13-dioxo-2,3,4,5,6,6a,7,8,8a,11,12,14b-dodecahydro-1H-picene-4a-carboxylic acid
• CAS: 73047-75-3
• 化学式: C₃₀H₄₄O₄
• 分子量: 468.677
• InChiKey: GZKMFYLBPHPWEI-DSBPZZANSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  34
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  71.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N,N'-羰基二(1,2,4-三氮唑) 、 3,11-dioxours-12-en-28-oic acid 以 四氢呋喃 为溶剂， 反应 4.0h， 以43%的产率得到(4aR,6aR,6bS,8aS,11R,12S,12aS,14aR,14bS)-4,4,6a,6b,11,12,14b-heptamethyl-8a-(1,2,4-triazole-4-carbonyl)-2,4a,5,6,7,8,9,10,11,12,12a,14a-dodecahydro-1H-picene-3,14-dione
  参考文献：
  名称：

  用抗增殖和p53的诱导，p21基因的能力改进的新颖熊果酸的杂环衍生物的合成WAF1在胰腺癌细胞和NOXA

  摘要：

  合成了一系列新的熊果酸1杂环衍生物，并评估了它们对AsPC-1胰腺癌细胞的抗增殖活性。具有α，β不饱和酮与A环中的杂环结合的化合物24-32具有增强的抗增殖活性。化合物32是活性最高的化合物，IC 50为1.9μM，活性是乌索酸1的七倍。化合物32个在G1期和诱导阻止细胞周期在ASPC-1细胞凋亡与p53，p21基因的上调WAF1和NOXA蛋白水平。

  DOI：

  10.1016/j.bmc.2012.08.010
• 作为产物：
  描述：

  熊果酸 在 potassium dichromate 、 硫酸 作用下， 以 溶剂黄146 为溶剂， 反应 1.5h， 以72%的产率得到3,11-dioxours-12-en-28-oic acid
  参考文献：
  名称：

  熊果酸某些衍生物的制备及其抗菌活性

  摘要：

  作者研究了生产抗肿瘤制剂 Rosevin 的工业废物，其中发现了约 18% 的熊果酸。他们通过在不同介质中用铬酸和 KMnO/sub 4/ 氧化获得了几种熊果酸的氧取代衍生物，以研究它们的生物活性。所得化合物的结构由IR和PMR光谱数据以及分子质谱数据证实，其中分子在电子撞击下电离。

  DOI：

  10.1007/bf00758617

文献信息

• Synthesis and α-Glucosidase Inhibitory Activity of Ursolic Acid, Lupeol, and Betulinic Acid Derivatives
  作者：Ngoc-Hong Nguyen、Duc Dung Pham、Thi-Thanh-Van Le、Thi-Anh-Tuyet Nguyen、Dinh-Long Huynh、Thuc-Huy Duong、Jirapast Sichaem

  DOI：10.1007/s10600-021-03545-1

  日期：2021.11

  Seven synthetic derivatives of ursolic acid, lupeol, and betulinic acid (1a–1b, 2a–2b, and 3a–3c) were synthesized to study their α-glucosidase inhibitory activity. Three of them (2b, 3b, and 3c) are new compounds. Among the synthetic derivatives, betulinic acid analogues 3b and 3c exhibited the best activity against α-glucosidase and is superior to the positive agent, with IC50 values of 35.0 ± 3.37 and 34.0 ± 1.24 μM, respectively.

  为了研究熊果酸、羽扇豆醇和白桦脂酸的α-葡萄糖苷酶抑制活性，我们合成了熊果酸、羽扇豆醇和白桦脂酸的七种合成衍生物（1a-1b、2a-2b 和 3a-3c）。其中三个（2b、3b 和 3c）是新化合物。在合成的衍生物中，白桦脂酸类似物 3b 和 3c 对α-葡萄糖苷酶的活性最好，优于阳性药，其 IC50 值分别为 35.0 ± 3.37 和 34.0 ± 1.24 μM。
• Oxidative lactonization of oleanane and ursane acids by treating with ozone
  作者：E. F. Husnutdinova、A. N. Lobov、O. S. Kukovinets、V. E. Kataev、O. B. Kazakova

  DOI：10.1134/s1070428015020219

  日期：2015.2

  Features of process of oxidative lactonization of 3-oxooleanolic and 3-oxoursolic acids under treatment with ozone were established. The similarity of the processes consists in generation of 3-oxooleanolic or 3-oxoursolic 13 beta,28-lactones with 12-oxo or 12-hydroxy group. In the case of ursane derivative the generation exclusively of compounds with beta-oriented 12-hydroxy group was observed, in the case of oleanane lactones prevailingly compounds with alpha-oriented 12-hydroxy group were obtained. The processes differ by the generation of the product of allylic oxidation, 3,11-dioxoursolic acid, or the isolation of the product of the lactone cycle opening with participation of the solvent, 3,12-dioxoolean-28-olic acid.
• Study of the structure of an a-seco compound produced by the oxidation of ursolic acid
  作者：I. I. Zaletova、N. A. Klyuev、I. V. Yartseva、O. N. Tolkachev

  DOI：10.1007/bf00598671

  日期：1987.9
• Synthesis of novel ursolic acid heterocyclic derivatives with improved abilities of antiproliferation and induction of p53, p21waf1 and NOXA in pancreatic cancer cells
  作者：Ana S. Leal、Rui Wang、Jorge A.R. Salvador、Yongkui Jing

  DOI：10.1016/j.bmc.2012.08.010

  日期：2012.10

  heterocyclic derivatives of ursolic acid 1 were synthesized and evaluated for their antiproliferative activity against AsPC-1 pancreatic cancer cells. Compounds 24–32, with an α,β unsaturated ketone in conjugation with an heterocyclic ring in ring A have improved antiproliferative activities. Compound 32 is the most active compound with an IC50 of 1.9 μM which is sevenfold more active than ursolic acid 1. Compound

  合成了一系列新的熊果酸1杂环衍生物，并评估了它们对AsPC-1胰腺癌细胞的抗增殖活性。具有α，β不饱和酮与A环中的杂环结合的化合物24-32具有增强的抗增殖活性。化合物32是活性最高的化合物，IC 50为1.9μM，活性是乌索酸1的七倍。化合物32个在G1期和诱导阻止细胞周期在ASPC-1细胞凋亡与p53，p21基因的上调WAF1和NOXA蛋白水平。
• Preparation of certain derivatives of ursolic acid and their antimicrobial activity
  作者：N. I. Zaletova、A. N. Shchavlinskii、O. N. Tolkachev、S. A. Vichkanova、T. V. Fateeva、N. M. Krutikova、I. V. Yartseva、N. A. Klyuev

  DOI：10.1007/bf00758617

  日期：1986.5

  The authors studied the industrial wastes from the production of an antitumorigenic preparation rosevin, in which about 18% of ursolic acid was found. They obtained several oxygen-substituted derivatives of ursolic acid by oxidation with chromic acid and KMnO/sub 4/ in different media to study their biological activity. The structure of the compounds obtained was confirmed by the data of IR and PMR

  作者研究了生产抗肿瘤制剂 Rosevin 的工业废物，其中发现了约 18% 的熊果酸。他们通过在不同介质中用铬酸和 KMnO/sub 4/ 氧化获得了几种熊果酸的氧取代衍生物，以研究它们的生物活性。所得化合物的结构由IR和PMR光谱数据以及分子质谱数据证实，其中分子在电子撞击下电离。