benzyl 2,4-bis(benzyloxy)-6-(((trifluoromethyl)sulfonyl)-oxy) benzoate | 1243583-64-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: benzyl 2,4-bis(benzyloxy)-6-(((trifluoromethyl)sulfonyl)-oxy) benzoate
• 英文别名: benzyl 2,4-bis(benzyloxy)-6-(((trifluoromethyl)sulfonyl)oxy)benzoate
• CAS: 1243583-64-3
• 化学式: C₂₉H₂₃F₃O₇S
• 分子量: 572.559
• InChiKey: FNWRQQKUXZJSTQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.43
• 重原子数：
  40.0
• 可旋转键数：
  11.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  88.13
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  1-癸炔 、 benzyl 2,4-bis(benzyloxy)-6-(((trifluoromethyl)sulfonyl)-oxy) benzoate 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 二乙胺 作用下， 以 乙腈 为溶剂， 反应 0.5h， 以79%的产率得到benzyl 2,4-bis(benzyloxy)-6-(dec-1-yn-1-yl) benzoate
  参考文献：
  名称：

  Improved inhibition of the histone acetyltransferase PCAF by an anacardic acid derivative

  摘要：

  Several lines of evidence indicate that histone acetyltransferases (HATs) are novel drug targets for treatment of diseases like, for example, cancer and inflammation. The natural product anacardic acid is a starting point for development of small molecule inhibitors of the histone acetyltransferase (HAT) p300/CBP associated factor (PCAF). In order to optimize the inhibitory potency, a binding model for PCAF inhibition by anacardic acid was proposed and new anacardic acid derivatives were designed. Ten new derivatives were synthesized using a novel synthetic route. One compound showed a twofold improved inhibitory potency for the PCAF HAT activity and a twofold improved inhibition of histone acetylation in HEP G2 cells. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.06.089
• 作为产物：
  描述：

  benzyl 2,4-bis(benzyloxy)-6-hydroxybenzoate 、 三氟甲磺酸酐 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 以56%的产率得到benzyl 2,4-bis(benzyloxy)-6-(((trifluoromethyl)sulfonyl)-oxy) benzoate
  参考文献：
  名称：

  Improved inhibition of the histone acetyltransferase PCAF by an anacardic acid derivative

  摘要：

  Several lines of evidence indicate that histone acetyltransferases (HATs) are novel drug targets for treatment of diseases like, for example, cancer and inflammation. The natural product anacardic acid is a starting point for development of small molecule inhibitors of the histone acetyltransferase (HAT) p300/CBP associated factor (PCAF). In order to optimize the inhibitory potency, a binding model for PCAF inhibition by anacardic acid was proposed and new anacardic acid derivatives were designed. Ten new derivatives were synthesized using a novel synthetic route. One compound showed a twofold improved inhibitory potency for the PCAF HAT activity and a twofold improved inhibition of histone acetylation in HEP G2 cells. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.06.089

文献信息

• Anacardic acid derived salicylates are inhibitors or activators of lipoxygenases
  作者：Rosalina Wisastra、Massimo Ghizzoni、André Boltjes、Hidde J. Haisma、Frank J. Dekker

  DOI：10.1016/j.bmc.2012.06.019

  日期：2012.8

  responses. Selective inhibitors may provide a new therapeutic approach for inflammatory diseases. In this study, we describe the identification of a novel soybean lipoxygenase-1 (SLO-1) inhibitor and a potato 5-lipoxygenase (5-LOX) activator from a screening of a focused compound collection around the natural product anacardic acid. The natural product anacardic acid inhibits SLO-1 with an IC50 of

  脂加氧酶催化不饱和脂肪酸的氧化，例如亚油酸，它们在炎症反应中起关键作用。选择性抑制剂可能为炎症性疾病提供一种新的治疗方法。在这项研究中，我们描述了一种新型的大豆脂氧合酶1（SLO-1）抑制剂和马铃薯5-脂氧合酶（5-LOX）活化剂的鉴定，该筛查是通过围绕天然产物无心果酸的集中化合物的筛选进行的。天然产物熊果酸抑制SLO-1的IC 50为52μM，而新型混合型抑制剂23的抑制能力提高了五倍。此外，另一种导数（21）引起了马铃薯5-LOX的不必要的激活。这表明存在调节脂肪氧化酶活性的变构结合位点。
• 6-alkylsalicylates are selective Tip60 inhibitors and target the acetyl-CoA binding site
  作者：Massimo Ghizzoni、Jiang Wu、Tielong Gao、Hidde J. Haisma、Frank J. Dekker、Y. George Zheng

  DOI：10.1016/j.ejmech.2011.11.001

  日期：2012.1

  Histone acetyltransferases are important enzymes that regulate various cellular functions, such as epigenetic control of DNA transcription. Development of HAT inhibitors with high selectivity and potency will provide powerful mechanistic tools for the elucidation of the biological functions of HATs and may also have pharmacological value for potential new therapies. In this work, analogs of the known HAT inhibitor anacardic acid were synthesized and evaluated for inhibition of HAT activity. Biochemical assays revealed novel anacardic acid analogs that inhibited the human recombinant enzyme Tip60 selectively compared to PCAF and p300. Enzyme kinetics studies demonstrated that inhibition of Tip60 by one such novel anacardic acid derive, 20, was essentially competitive with Ac-CoA and non-competitive with the histone substrate. In addition, these HAT inhibitors effectively inhibited acetyltransferase activity of nuclear extracts on the histone H3 and H4 at micromolar concentrations. (C) 2011 Elsevier Masson SAS. All rights reserved.