2,5-dihydroxy-3-octylcyclohexa-2,5-diene-1,4-dione | 21182-47-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,5-dihydroxy-3-octylcyclohexa-2,5-diene-1,4-dione
• CAS: 21182-47-8
• 化学式: C₁₄H₂₀O₄
• 分子量: 252.31
• InChiKey: FQAUQBOULILEAV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  对三氟甲基苯甲醛 、 2,5-dihydroxy-3-octylcyclohexa-2,5-diene-1,4-dione 、 3-氨基-5-苯基吡唑 在 ethylenediamine Tetraacetic Acid 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 0.17h， 以43%的产率得到6-hydroxy-7-octyl-3-phenyl-4-(4-(trifluoromethyl)phenyl)-1H-pyrazolo[3,4-b]quinoline-5,8(4H,9H)-dione
  参考文献：
  名称：

  新型二氢-1H-吡唑并[1,3-b]吡啶Embelin衍生物的模块化合成及抗增殖活性

  摘要：

  以天然embelin、3-取代-5-氨基吡唑和醛类为原料，通过多组分反应合成了一组新的二氢-1H-吡唑并[1,3 - b ]吡啶和吡唑并[1,3- b ]吡啶embelin衍生物。合成的化合物针对三种血液肿瘤细胞系 HEL（急性红系白血病）、K-562（慢性髓系白血病）和 HL-60（急性髓系白血病）以及五种乳腺癌细胞系（SKBR3、MCF-7、 MDA-MB-231、BT-549、HS-578T）。灵长类非恶性肾Vero细胞系用作细胞毒性的对照。从获得的结果中，概述了一些结构-活性关系。此外，在硅 确定了具有最佳抗增殖值的衍生物的理化性质和 ADME 参数的预测。

  DOI：

  10.3390/ph14101026
• 作为产物：
  描述：

  2,5-二羟基-1,4-苯喹酮 在 盐酸 、 正丁基锂 、 palladium 10% on activated carbon 、 氢气 、 4-甲基苯磺酸吡啶 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醇 、 正己烷 、 水 、 甲苯 为溶剂， -10.0~25.0 ℃ 、500.01 kPa 条件下， 反应 95.5h， 生成 2,5-dihydroxy-3-octylcyclohexa-2,5-diene-1,4-dione
  参考文献：
  名称：

  Design, synthesis, and SAR of embelin analogues as the inhibitors of PAI-1 (plasminogen activator inhibitor-1)

  摘要：

  The natural product embelin was found to have PAI-1 inhibitory activity with the IC50 value of 4.94 mu M. Based on the structure of embelin, a series of analogues were designed, synthesized, and evaluated for their ability to inhibit PAI-1. The SAR study on these compounds disclosed that the inhibitory potency largely depended on the hydroxyl groups at C2 and C5, and the length of the alkyl chains at C3 and C6. Compound 11 displayed the best PAI-1 inhibitory potency with the IC50 value of 0.18 mu M. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.03.045

文献信息

• A new family of densely functionalized fused-benzoquinones as potent human protein kinase CK2 inhibitors
  作者：Pedro Martín-Acosta、Samer Haider、Ángel Amesty、Dagmar Aichele、Joachim Jose、Ana Estévez-Braun

  DOI：10.1016/j.ejmech.2017.12.058

  日期：2018.1

  A new series of 2-amino-4-phenyl-6-hydroxy-7-alkyl-pyranobenzoquinones was synthesized as ATP-competitive CK2 inhibitors. They were readily synthesized through a three-component Knoevenagel condensation-Michael addition-heterocyclization reaction from aldehydes, malononitrile, and 3-alkyl-2,5-dihydroxybenzoquinones. Some of the synthesized compounds presented interesting inhibitory activity with IC50

  合成了一系列新的2-氨基-4-苯基-6-羟基-7-烷基-吡喃苯并醌作为ATP竞争性CK2抑制剂。它们很容易通过醛，丙二腈和3-烷基-2,5-二羟基苯醌的三组分Knoevenagel缩合反应-Michael加成-杂环反应合成。一些合成的化合物表现出令人感兴趣的抑制活性，其IC 50值在亚微摩尔范围内。进行了结构-活性关系研究，并通过对接研究分析了结合方式，并得到了ATP竞争测定法的支持。
• Novel series of benzoquinones with high potency against 5-lipoxygenase in human polymorphonuclear leukocytes
  作者：Rosanna Filosa、Antonella Peduto、Anja M. Schaible、Verena Krauth、Christina Weinigel、Dagmar Barz、Carmen Petronzi、Ferdinando Bruno、Fiorentina Roviezzo、Giuseppe Spaziano、Bruno D'Agostino、Mario De Rosa、Oliver Werz

  DOI：10.1016/j.ejmech.2015.02.042

  日期：2015.4

  intervention with various inflammatory and allergic diseases. Starting from the natural dual 5-LO/microsomal prostaglandin E2 synthase (mPGES)-1 inhibitor embelin (2,5-dihydroxy-3-undecyl-1,4-benzoquinone, 2) that suppresses 5-LO activity in human primary leukocytes with IC50 = 0.8–2 μM, we synthesized 48 systematically modified derivatives of 2. We modified the 1,4-quinone to 1,2-quinone, mono- or bimethylated

  5-Lipoxygenase（5-LO）是各种炎症和过敏性疾病的药理干预措施的潜在目标。从天然的双重5-LO /微粒体前列腺素E 2合酶（mPGES）-1抑制剂embelin（2,5-dihydroxy-3-undecyl-1,4-benzoquinone，2）抑制人类原代白细胞中的5-LO活性。 IC 50  = 0.8–2μM，我们合成了2的48个系统修饰的衍生物。我们修改了1,4-醌1,2-醌，单-或bimethylated的羟基，并且改变所述C11- Ñ -烷基残基（C 4 -至C 16 ñ -烷基或异戊烯基）的2。生物学评估产生的有效类似物优于2和明显的构效关系（SAR）抑制5-LO。有趣的是，转化成1,2-苯醌和羟基部分的二甲基化大大改善了多形核白细胞中的5-LO抑制，而对C2-正烷基衍生物22c（4,5-二甲氧基-3）的抑制则高达2倍，提高了60倍。-十二烷基-1,2-苯醌），IC
• Biochemical Studies on Benzoquinone Derivatives. V. Structure-Activity Relationship between Benzoquinone Derivatives and Inhibition of Respiration of Rat Liver Intact Mitochondria
  作者：HIKARU OZAWA、KAZUTAKA MOMOSE、MOTOKO MACHIDA、SHINSAKU NATORI、KUNITOSHI YOSHIHIRA

  DOI：10.1248/cpb.16.853

  日期：——

  Alkyldihydroxy-p-benzoquinone and related compounds were newly prepared and effects of these compounds on a respiration of rat liver intact mitochondria were examined. Structure activity relationship between the benzoquinone derivatives and effects on the mitochondrial respiration was discussed. 1. 2-Methyl-5-octyl-3, 6-dihydroxy-1, 4-benzoquinone and ardisiaquinone B showed specific inhibition of State-3 respiration. But in high concentration they inhibited both State-3 and State-4 respiration. 2. 2-Octyl-3, 5-diydroxy-1, 4-benzoquinone and ardisiaquinone A inhibited both State-3 and State-4 respiration. 3. Rapanone, maesaquinone, polygonaquinone and related compounds having longer alkyl chains did not show any effect. As the result carbon numbers of the side chain have been found to be an important factor to exhibit the activity.

  新制备了烷基二羟基-p-姜黄酮及相关化合物，并研究了这些化合物对大鼠肝脏完整线粒体呼吸的影响。讨论了苯醌衍生物与线粒体呼吸影响之间的结构-活性关系。1. 2-甲基-5-辛基-3, 6-二羟基-1, 4-苯醌和阿尔迪西亚醌B对状态3呼吸表现出特异性抑制，但在高浓度下会抑制状态3和状态4呼吸。2. 2-辛基-3, 5-二羟基-1, 4-苯醌和阿尔迪西亚醌A同时抑制状态3和状态4呼吸。3. 拉帕酮、梅萨醌、Polygonum醌及相关的长烷基链化合物没有表现出任何效果。结果表明，侧链的碳数是表现活性的一个重要因素。
• Design, synthesis, and characterization of new embelin derivatives as potent inhibitors of X-linked inhibitor of apoptosis protein
  作者：Jianyong Chen、Zaneta Nikolovska-Coleska、Guoping Wang、Su Qiu、Shaomeng Wang

  DOI：10.1016/j.bmcl.2006.08.072

  日期：2006.11

  X-Linked inhibitor of apoptosis protein (XIAP) is a promising molecular target for the design of new anticancer drugs aiming at promoting apoptosis in cancer cells. We have previously identified embelin as an inhibitor of XIAP through computational structure-based database screening. Herein, we report the design, synthesis, and evaluation of new embelin analogues as inhibitors of XIAP. Our efforts led to the identification of new and more potent inhibitors. For example, compound 6g has a K-i value of 180 nM binding to XIAP BIR3, in a competitive binding assay and represents a promising lead compound for further optimization. (c) 2006 Elsevier Ltd. All rights reserved.
• Small Molecule Antagonists of Xiap Family Proteins
  申请人：Chen Jianyong

  公开号：US20080021095A1

  公开（公告）日：2008-01-24

  The present invention relates to naturally occurring and chemically synthesized small molecule antagonists of XIAP family proteins. In particular, the present invention provides embelin and other XIAP inhibitors and methods of using these compounds as antagonists of the anti-apoptotic effects of XIAP family member proteins. The present invention also provides methods for treating diseases and pathologies (e.g., neoplastic diseases).