5-hydroxy-4-isobutyryl-2,2,6,6-tetrakis(3-methylbut-2-en-1-yl)-cyclohex-4-ene-1,3-dione | 16658-23-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-hydroxy-4-isobutyryl-2,2,6,6-tetrakis(3-methylbut-2-en-1-yl)-cyclohex-4-ene-1,3-dione
• 英文别名: Colupone；5-hydroxy-2,2,6,6-tetrakis(3-methylbut-2-enyl)-4-(2-methylpropanoyl)cyclohex-4-ene-1,3-dione
• CAS: 16658-23-4
• 化学式: C₃₀H₄₄O₄
• 分子量: 468.677
• InChiKey: KPPHPIMYCLGAER-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.6
• 重原子数：
  34
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  71.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  phlorisobutyrophenone 、 1-溴-3-甲基-2-丁烯 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 以28%的产率得到5-hydroxy-4-isobutyryl-2,2,6,6-tetrakis(3-methylbut-2-en-1-yl)-cyclohex-4-ene-1,3-dione
  参考文献：
  名称：

  Triketones active against antibiotic-resistant bacteria: Synthesis, structure–activity relationships, and mode of action

  摘要：

  A series of acylated phloroglucinols and triketones was synthesized and tested for activity against methicillin-resistant Staphylococcus aureus (MRSA), vancomycin-resistant Enterococcus faecalis (VRE) and multi-drug-resistant Mycobacterium tuberculosis (MDR-TB). A tetra-methylated triketone with a C-12 side chain was the most active compound (MIC of around 1.0 mu g/ml against MRSA) and was shown to stimulate oxygen consumption by resting cell suspensions, suggesting that the primary target was the cytoplasmic membrane. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.07.045

文献信息

• Synthesis and P-glycoprotein induction activity of colupulone analogs
  作者：Jaideep B. Bharate、Yazan S. Batarseh、Abubakar Wani、Sadhana Sharma、Ram A. Vishwakarma、Amal Kaddoumi、Ajay Kumar、Sandip B. Bharate

  DOI：10.1039/c5ob00554j

  日期：——

  treatment of AD. Colupulone, a prenylated phloroglucinol isolated from Humulus lupulus, is known to activate pregnane-X-receptor (PXR), which is a nuclear receptor controlling P-gp expression. In the present work, we aimed to synthesize and identify analogs of colupulone that are potent P-gp inducer(s) with an ability to enhance Aβ transport across the BBB. A series of colupulone analogs were synthesized

  脑淀粉样蛋白（Aβ）斑块是与阿尔茨海默氏病（AD）病理相关的主要标志之一。据报道，位于血脑屏障（BBB）的外排泵蛋白在清除大脑Aβ中起重要作用，其中P-糖蛋白（P-gp）外排转运泵已显示出至关重要的作用。因此，P-gp已被认为是治疗AD的潜在治疗靶标。Colupulone，一种从Hum草中分离的烯丙基间苯三酚已知其激活孕烷-X-受体（PXR），后者是控制P-gp表达的核受体。在目前的工作中，我们旨在合成和鉴定具有强大的P-gp诱导剂能力的colupulone类似物，并具有增强Aβ通过BBB转运的能力。通过在异戊二烯基和酰基域上的修饰合成了一系列的colupulone类似物。在过表达P-gp的人腺癌LS-180细胞中，使用基于若丹明123的外排试验筛选所有化合物的P-gp诱导活性，其中所有化合物在5μM下显示出显着的P-gp诱导活性。在LS-180细胞中的蛋白质印迹研究中，化合物3k和5f能
• Triketones active against antibiotic-resistant bacteria: Synthesis, structure–activity relationships, and mode of action
  作者：John W. van Klink、Lesley Larsen、Nigel B. Perry、Rex T. Weavers、Gregory M. Cook、Phil J. Bremer、Andrew D. MacKenzie、Teruo Kirikae

  DOI：10.1016/j.bmc.2005.07.045

  日期：2005.12

  A series of acylated phloroglucinols and triketones was synthesized and tested for activity against methicillin-resistant Staphylococcus aureus (MRSA), vancomycin-resistant Enterococcus faecalis (VRE) and multi-drug-resistant Mycobacterium tuberculosis (MDR-TB). A tetra-methylated triketone with a C-12 side chain was the most active compound (MIC of around 1.0 mu g/ml against MRSA) and was shown to stimulate oxygen consumption by resting cell suspensions, suggesting that the primary target was the cytoplasmic membrane. (c) 2005 Elsevier Ltd. All rights reserved.