1,4-二氯-2-氟苯 | 71623-71-7

• 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
• 中文名称: 1,4-二氯-2-氟苯
• 英文名称: 3β-acetoxy-11-oxours-12-en-28-oic acid
• 英文别名: 11-oxo-3-O-acetylursolic acid；3-O-acetyl-11-oxoursolic acid；3-acetyl-11-keto-ursolic acid；11-oxo-3O-acetylursolic acid；11-oxo-ursolic acid acetate；11-oxo acetyl ursolic acid；11-Oxoursolic acid acetate；(1S,2R,4aS,6aR,6aS,6bR,8aR,10S,12aS,14bS)-10-acetyloxy-1,2,6a,6b,9,9,12a-heptamethyl-13-oxo-1,2,3,4,5,6,6a,7,8,8a,10,11,12,14b-tetradecahydropicene-4a-carboxylic acid
• CAS: 71623-71-7；35959-01-4
• 化学式: C₃₂H₄₈O₅
• 分子量: 512.73
• InChiKey: XDHCWTUZCOFKRH-CIKBGXLUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  37
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  80.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,4-二氯-2-氟苯 生成 11-氧代熊果酸
  参考文献：
  名称：

  Complete assignments of1H and13C NMR resonances of oleanolic acid, 18?-oleanolic acid, ursolic acid and their 11-oxo derivatives

  摘要：

  基于 1H、13C、2D DQF-COSY、NOESY、HSQC、HMBC 和 HSQC-TOCSY 实验，实现了齐墩果酸、18α-齐墩果酸、熊果酸及其 11-oxo 衍生物 1H 和 13C NMR 化学位移的完整分配。Copyright © 2003 John Wiley & Sons, Ltd. All Rights Reserved.

  DOI：

  10.1002/mrc.1214
• 作为产物：
  描述：

  熊果酸 在 吡啶 、 叔丁基过氧化氢 、 sodium chlorite 作用下， 反应 26.0h， 生成 1,4-二氯-2-氟苯
  参考文献：
  名称：

  熊果酸衍生物下调炎症介质

  摘要：

  熊果酸（UA）因其抗炎潜力而受到研究，结构修饰可以增强其生物活性。本研究的目的是评估熊果酸衍生物 (UAD) 在巨噬细胞和角叉菜胶诱导的足水肿模型中的免疫调节作用。 RAW264.7 细胞在存在或不存在 UA 或 UAD 的情况下培养 (1-18)。测量一氧化氮 (NO)、核因子 kappa B (NF-κB)、肿瘤坏死因子 (TNF) 和细胞活力。在角叉菜胶引起的爪水肿前30分钟，腹膜内施用UAD1和UAD2（200 mg kg-1）。结果显示，UAD2-4、UAD7、UAD9-11 的半数最大抑制浓度 (IC50) 大于 90 µM，能够减少 NO、NF-κB 和 TNF 的产生。此外，UAD1 和 UAD2 减少爪水肿和 IL-6 的产生。总之，所获得的结果表明，由于化学修饰，衍生物之间的反应存在差异，显示出减少炎症介质的潜力，值得进一步研究。

  DOI：

  10.21577/0103-5053.20230036

文献信息

• Synthesis of Norhydroperoxides from Natural Triterpenic Acids
  作者：Eugene S. Tatarov、Alexey V. Tkachev

  DOI：10.1135/cccc20011753

  日期：——

  Treatment of triterpenoids derived from ursolic and glycyrrhetinic acids with the oxidative mixture H₂O₂-(CF₃COO)₂Hg-Na₂CO₃-THF results in oxidative decarboxylation. The reaction of 3O-acetylursolic acid (1) and 3O-acetyl-18β-glycyrrhetinic acid (3) affords stable norhydroperoxides, whereas decarboxylation of 3O-acetyl-11-oxoursolic acid (6) leads to unstable norhydroperoxide. The difference in properties of the norhydroperoxides is explained by the presence of a conjugated ketone, which activates the 12,13-C=C double bond for nucleophilic addition and makes possible intramolecular Michael-type addition of peroxo anion.

  来源于熊果酸和甘草酸的三萜类化合物在氧化混合物H₂O₂-(CF₃COO)₂Hg-Na₂CO₃-THF的作用下发生氧化脱羧反应。3O-乙酰基熊果酸（1）和3O-乙酰基-18β-甘草酸（3）的反应产生稳定的羟过氧化物，而3O-乙酰基-11-氧基熊果酸（6）的脱羧反应导致不稳定的羟过氧化物。羟过氧化物性质的差异可通过存在的共轭酮来解释，该酮激活12,13-C=C双键进行亲核加成，并实现过氧化物阴离子的分子内迈克尔型加成。
• 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。
• Synthesis and in vitro Cytotoxicity of Novel Ursolic Acid Derivatives
  作者：Yanqiu Meng、Yanling Song、Zhaokai Yan、Yan Xia

  DOI：10.3390/molecules15064033

  日期：——

  In an effort to improve potential hepatoprotective and anti-tumor activities, eight novel ursolic acid (UA) derivatives were designed and synthesized with substitution at positions of C-3, C-11and C-28 of UA. Their structures were confirmed using IR, MS and 1H-NMR and elemental analysis. Their in vitro cytotoxicity against various cancer cell lines (HeLa, SKOV3 and BGC-823) was evaluated by the standard MTT assay. Among them, compound 13 exhibited more potent cytotoxicity than ursolic acid.

  为了提高潜在的保肝和抗肿瘤活性，研究人员设计并合成了八种新型熊果酸（UA）衍生物，并对 UA 的 C-3、C-11 和 C-28 位置进行了取代。通过红外光谱、质谱和 1H-NMR 以及元素分析确认了它们的结构。它们对各种癌细胞株（HeLa、SKOV3 和 BGC-823）的体外细胞毒性通过标准的 MTT 试验进行了评估。其中，化合物 13 比熊果酸表现出更强的细胞毒性。
• Oxyfunctionalization Products of Terpenoids with Dimethyldioxirane and Their Biological Activity
  作者：Shoujiro Ogawa、Keiji Hosoi、Noriaki Ikeda、Mitsuko Makino、Yasuo Fujimoto、Takashi Iida

  DOI：10.1248/cpb.55.247

  日期：——

  Oxyfunctionalization of the bioactive terpenoids, ursolic acid acetate (1), oleanolic acid acetate (5), lupeol acetate (12), and kaurenic acid (17), with dimethyldioxirane (DMDO) was investigated. Treatment of the terpenoids with DMDO under mild conditions afforded a variety of oxidation and oxydegradation products to yield naturally occurring and/or novel compounds in one step. After chromatographic separation, the structures of the individual isolated products were determined using spectroscopic methods including several homonuclear (1H–1H) and heteronuclear (1H–13C) shift-correlated 2D-NMR techniques. The inhibitory activity of the terpenoid derivatives against α-glucosidase was investigated and compounds 1, 3, 7, and 9 were found to exhibit potent activity.

  研究人员用二甲基二氧环己烷（DMDO）对具有生物活性的萜类化合物熊果酸乙酸酯（1）、齐墩果酸乙酸酯（5）、羽扇豆醇乙酸酯（12）和高瑞香酸（17）进行了氧化官能化处理。在温和的条件下，用二甲基二氧环己烷处理萜类化合物，可产生多种氧化和氧降解产物，从而一步生成天然和/或新型化合物。色谱分离后，利用光谱方法（包括几种同核（1H-1H）和异核（1H-13C）位移相关的二维核磁共振技术）确定了各个分离产物的结构。研究了萜类衍生物对 α-葡萄糖苷酶的抑制活性，发现化合物 1、3、7 和 9 具有很强的活性。
• 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。