bromoenol lactone | 88070-98-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: bromoenol lactone
• 英文别名: BEL；(E)-6-(bromomethylene)tetrahydro-3-(1-naphthalenyl)-2H-pyran-2-one；B 1552；(6E)-6-(bromomethylidene)-3-naphthalen-1-yloxan-2-one
• CAS: 88070-98-8
• 化学式: C₁₆H₁₃BrO₂
• 分子量: 317.182
• InChiKey: BYUCSFWXCMTYOI-ZRDIBKRKSA-N

物化性质

• 熔点：
  103-106℃
• 沸点：
  467.0±45.0 °C(Predicted)
• 密度：
  1.538±0.06 g/cm3(Predicted)
• 溶解度：
  DMSO：使用前立即在水性介质中稀释，冷藏储存不超过12小时。
• 稳定性/保质期：

  按照规定使用和贮存的这些物质不会分解，也能够避免与氧化物接触。

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险品标志：
  Xi
• 危险类别码：
  R36/37/38
• 安全说明：
  S26

制备方法与用途

生物活性

Bromoenol LActone ((6E)-Bromoenol LActone) 是一种不可逆的选择性和有效的钙依赖性磷脂酶 A2 (iPLA2β) 抑制剂，其 IC50 值约为 7 μM。它能够抑制抗原刺激的肥大细胞胞吐作用，而不会阻止 Ca2+ 的大量涌入。

靶点	PLA2	7 μM (IC50)

体外研究

在 RBL 2H3 和骨髓衍生的嗜碱性粒细胞（BMMCs）中，Ca2+ 内流是胞吐作用的关键。Bromoenol LActone 在使用 A23187 离子载体进行刺激时能够抑制胞吐作用，A23187 通过浓度梯度被动运输 Ca2+。此外，在渗透化的嗜碱性粒细胞中，Ca2+ 内流不再相关的情况下，Bromoenol LActone 仍然能有效抑制抗原或 thapsigargin 刺激的 Ca2+ 信号传导，包括内储池释放和由于 Ca2+ 内流引起的持续升高。

反应信息

• 作为反应物：
  描述：

  bromoenol lactone 在 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 2.0h， 生成 6-bromo-2-(1-naphtyl)-5-oxohexanoic acid
  参考文献：
  名称：

  Calcium-independent phospholipases A2 in murine osteoblastic cells and their inhibition by bromoenol lactone: impact on arachidonate dynamics and prostaglandin synthesis

  摘要：

  Context: Bromoenol lactone (BEL) is an inhibitor of group VI phospholipases (iPLA(2)s), but has been shown to have severe side effects. Objective: iPLA(2) characterization in osteoblasts and effect of BEL on prostaglandin (PG) E-2 formation. Methods: iPLA(2) expression: RT-PCR, Western Blotting. PGE(2) formation: GC-MS after stimulation, treatment with inhibitors or gene silencing. Arachidonate (AA) reacylation into phospholipids, inhibitor reaction products, PGHS-1 modification proteomic analysis: HR-LC-MS/MS. AA accumulation: C-14-AA. Results: iPLA(2)beta and iPLA(2)gamma were expressed and functionally active. BEL inhibition up to 20 mM caused AA accumulation and enhanced PGE(2) formation, followed by a decrease at higher concentrations. BEL reacted with intracellular cysteine and GSH leading to GSH depletion and oxidative stress. Discussion: Initial PGE(2) enhancement after BEL inhibition is due to iPLA(2)-independent accumulation of AA. GSH depletion caused by high BEL concentrations is responsible for the decrease in PGE(2) production. Conclusion: BEL must be used with caution in a cellular environment due to conditions of extreme oxidative stress.

  DOI：

  10.3109/14756366.2015.1114929

文献信息

• HERBICIDAL COMPOSITIONS COMPRISING NAPTALAM
  申请人：Patzoldt William L.

  公开号：US20110287935A1

  公开（公告）日：2011-11-24

  The present invention relates to herbicidal compositions comprising a) a herbicide compound A which is selected from Λ/-1-naphthylphthalamic acid (naptalam), the salts and esters thereof; and b) a herbicide compound B which is selected from b.1 3,6-dichloro-2-methoxybenzoic acid (dicamba), the salts and esters thereof; b.2 quinolinecarboxylic acid herbicides; b.3 pyridinecarboxylic acid herbicides; and b.4 aminocyclopyrachlor, the salts and esters thereof. The present invention also relates to the use of these compositions for controlling undesirable vegetation, in particular in crops, in turf or pasture, in rangeland, in fallow, or in forestry.

  本发明涉及杀草剂组合物，包括a）选择自Λ/-1-萘乙酸（naptalam）、其盐和酯的草甘膦化合物A；和b）选择自b.1 3,6-二氯-2-甲氧基苯甲酸（dicamba）、其盐和酯的草甘膦化合物B；b.2 喹啉羧酸类除草剂；b.3 吡啶羧酸类除草剂；和b.4 氨基环戊烯酸，其盐和酯。本发明还涉及使用这些组合物来控制不良植被，特别是在作物、草坪或牧场、荒地或林业中。
• Herbicidal compositions comprising naptalam
  申请人：Patzoldt William L.

  公开号：US08648012B2

  公开（公告）日：2014-02-11

  The present invention relates to herbicidal compositions comprising a) a herbicide compound A which is selected from Λ/-1-naphthylphthalamic acid (naptalam), the salts and esters thereof; and b) a herbicide compound B which is selected from b.1 3,6-dichloro-2-methoxybenzoic acid (dicamba), the salts and esters thereof; b.2 quinolinecarboxylic acid herbicides; b.3 pyridinecarboxylic acid herbicides; and b.4 aminocyclopyrachlor, the salts and esters thereof. The present invention also relates to the use of these compositions for controlling undesirable vegetation, in particular in crops, in turf or pasture, in rangeland, in fallow, or in forestry.

  本发明涉及除草剂组合物，包括a) 从Λ/-1-萘乙酸（naptalam），其盐和酯中选择的除草剂化合物A；和b) 从b.1 3,6-二氯-2-甲氧基苯甲酸（dicamba），其盐和酯中选择的除草剂化合物B；b.2 喹啉羧酸除草剂；b.3 吡啶羧酸除草剂；和b.4 aminocyclopyrachlor，其盐和酯。本发明还涉及使用这些组合物来控制不良植被，特别是在农作物、草坪或牧场、草原、休耕地或林业中。
• NOVEL LIPASE INHIBITORS, REPORTER SUBSTRATES AND USES THEREOF
  申请人：Northeastern University

  公开号：US20150099800A1

  公开（公告）日：2015-04-09

  The invention provides for novel lipase inhibitors, and compositions and devices comprising the same. The invention further provides for methods for treatment of disorders comprising administration of novel diacylglycerol lipase inhibitors, and compositions and devices comprising said inhibitors. In some embodiments, the disorders are pancreatitis, obesity, shock or pancreatic necrosis. The invention further provides for novel ether lipid reporter compounds and methods of assaying enzymatic activity comprising contacting a compound with a novel ether lipid reporter compound.

  本发明提供了新型脂肪酶抑制剂，以及包含它们的组合物和装置。本发明还提供了治疗疾病的方法，包括给予新型二酰基甘油脂肪酶抑制剂、含有该抑制剂的组合物和装置。在某些实施例中，这些疾病包括胰腺炎、肥胖症、休克或胰腺坏死。本发明还提供了新型醚脂质报告化合物和测定酶活性的方法，其中将化合物与新型醚脂质报告化合物接触。
• Ras PROTEIN DEGRADATION INDUCING MOLECULE AND PHARMACEUTICAL COMPOSITION
  申请人：Tokyo University of Science Foundation

  公开号：EP3542824A1

  公开（公告）日：2019-09-25

  A Ras protein degradation inducing molecule that can induce degradation of Ras proteins, and a pharmaceutical composition that contains this Ras protein degradation inducing molecule are provided. The Ras protein degradation inducing molecule is a conjugate of a Ras protein affinity molecule which has affinity to Ras proteins, and a proteolysis-inducing tag which has affinity to protease and does not inhibit proteolysis of proteins by the protease.

  本发明提供了一种可诱导 Ras 蛋白降解的 Ras 蛋白降解诱导分子，以及一种含有这种 Ras 蛋白降解诱导分子的药物组合物。Ras 蛋白降解诱导分子是与 Ras 蛋白亲和的 Ras 蛋白亲和分子和与蛋白酶亲和的蛋白水解诱导标签的共轭物，蛋白水解诱导标签不抑制蛋白酶对蛋白质的蛋白水解。
• Protein degradation inducing tag and usage thereof
  申请人：Tokyo University of Science Foundation

  公开号：US10976306B2

  公开（公告）日：2021-04-13

  Provided are: a protein degradation inducing tag which is a molecule that has affinity with proteases and does not inhibit degradation of a protein by proteases; a protein degradation inducing molecule that is a conjugate of at least one protein degradation inducing tag and at least one protein binding molecule that binds to a protein; and a usage of those.

  提供了：一种蛋白质降解诱导标签，它是一种与蛋白酶具有亲和力的分子，不会抑制蛋白酶对蛋白质的降解；一种蛋白质降解诱导分子，它是至少一种蛋白质降解诱导标签和至少一种与蛋白质结合的蛋白质结合分子的共轭物；以及它们的用法。