1,1'-<1,6-hexanediylbis(oxy-4,1-phenylene)>bisethanone | 99174-33-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,1'-<1,6-hexanediylbis(oxy-4,1-phenylene)>bisethanone
• 英文别名: 1,1’-((hexane-1,6-diylbis(oxy))bis(4,1-phenylene))diethanone；1,1'-((hexane-1,6-diylbis(oxy))bis(4,1-phenylene))diethanone；1,6-Bis-(4-acetyl-phenoxy)-hexan；1-[4-[6-(4-Acetylphenoxy)hexoxy]phenyl]ethanone
• CAS: 99174-33-1
• 化学式: C₂₂H₂₆O₄
• 分子量: 354.446
• InChiKey: HJPPGBISZPBZDX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  26
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,1'-<1,6-hexanediylbis(oxy-4,1-phenylene)>bisethanone 在 溴 作用下， 以 氯仿 为溶剂， 生成
  参考文献：
  名称：

  新型双噻唑衍生物的区域选择性合成及其抗菌活性

  摘要：

  描述了与单杂环类似物相比用作双药物的几种新双噻唑 4a-h 的设计和合成。这些双药对革兰氏阴性菌（铜绿假单胞菌和大肠杆菌）和革兰氏阳性菌（藤黄微球菌和枯草芽孢杆菌）均具有优异的药用和药理活性，这些细菌通常对疏水性较高的化合物更敏感。具有较高疏水性（4d 和 4h）的化合物对革兰氏阴性菌表现出一定的活性。

  DOI：

  10.1002/ardp.201300187
• 作为产物：
  描述：

  1-(4-羟基苯)乙醇 在 manganese(IV) oxide 、 potassium carbonate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成 1,1'-<1,6-hexanediylbis(oxy-4,1-phenylene)>bisethanone
  参考文献：
  名称：

  [EN] ECO-FRIENDLY MATERIALS AND METHODS FOR RENEWABLE AND SUSTAINABLE APPLICATIONS IN MATERIAL CHEMISTRY
  [FR] MATÉRIAUX ET PROCÉDÉS RESPECTUEUX DE L'ENVIRONNEMENT POUR DES APPLICATIONS RENOUVELABLES ET DURABLES DANS LA CHIMIE DES MATÉRIAUX

  摘要：

  该发明涉及新型基于肼酰肼的模板，制备方法以及将基于肼酰肼的模板用作不对称光驱动转化、光驱动材料合成和生物应用的分子支架的方法。此外，本发明涉及从生物质衍生的光引发剂、单体和聚合物，以及使用它们的方法。

  公开号：

  WO2017156066A1

文献信息

• Small Multitarget Molecules Incorporating the Enone Moiety
  作者：Thalia Liargkova、Nikolaos Eleftheriadis、Frank Dekker、Efstathia Voulgari、Constantinos Avgoustakis、Marina Sagnou、Barbara Mavroidi、Maria Pelecanou、Dimitra Hadjipavlou-Litina

  DOI：10.3390/molecules24010199

  日期：——

  Chalcones represent a class of small drug/druglike molecules with different and multitarget biological activities. Small multi-target drugs have attracted considerable interest in the last decade due their advantages in the treatment of complex and multifactorial diseases, since “one drug-one target” therapies have failed in many cases to demonstrate clinical efficacy. In this context, we designed and synthesized potential new small multi-target agents with lipoxygenase (LOX), acetyl cholinesterase (AChE) and lipid peroxidation inhibitory activities, as well as antioxidant activity based on 2-/4- hydroxy-chalcones and the bis-etherified bis-chalcone skeleton. Furthermore, the synthesized molecules were evaluated for their cytotoxicity. Simple chalcone b4 presents significant inhibitory activity against the 15-human LOX with an IC50 value 9.5 µM, interesting anti-AChE activity, and anti-lipid peroxidation behavior. Bis-etherified chalcone c12 is the most potent inhibitor of AChE within the bis-etherified bis-chalcones followed by c11. Bis-chalcones c11 and c12 were found to combine anti-LOX, anti-AchE, and anti-lipid peroxidation activities. It seems that the anti-lipid peroxidation activity supports the anti-LOX activity for the significantly active bis-chalcones. Our circular dichroism (CD) study identified two structures capable of interfering with the aggregation process of Aβ. Compounds c2 and c4 display additional protective actions against Alzheimer’s disease (AD) and add to the pleiotropic profile of the chalcone derivatives. Predicted results indicate that the majority of the compounds with the exception of c11 (144 Å) can cross the Blood Brain Barrier (BBB) and act in CNS. The results led us to propose new leads and to conclude that the presence of a double enone group supports better biological activities.

  查耳酮类药物代表了一类具有多种和多重靶点生物活性的小分子药物或类药分子。在过去的十年里，小型多靶点药物因其能够治疗复杂和多因素疾病的优点而引起了相当大的兴趣，因为“一种药物一个靶点”的治疗方法在许多情况下未能显示出临床疗效。在这种情况下，我们设计并合成了具有潜在的新小型多靶点药物，具有脂氧合酶（LOX）、乙酰胆碱酯酶（AChE）和脂质过氧化抑制活性，以及基于2-/4-羟基查耳酮和双醚化双查耳酮骨架的抗氧化活性。此外，合成的分子还对其细胞毒性进行了评估。简单的查耳酮b4对15-人LOX具有显著的抑制活性，IC50值为9.5 µM，具有有趣的抗AChE活性和抗脂质过氧化行为。双醚化查耳酮c12是双醚化双查耳酮中对AChE最有效的抑制剂，其次是c11。发现双查耳酮c11和c12具有抗LOX、抗AchE和抗脂质过氧化活性。看来抗脂质过氧化活性支持显著活性的双查耳酮的抗LOX活性。我们的圆二色性（CD）研究发现两种结构能够干扰Aβ的聚集过程。化合物c2和c4显示了额外的保护作用，防止阿尔茨海默病（AD）的发生，并增加了查耳酮衍生物的多效性特征。预测结果表明，除了c11（144 Å）之外，大多数化合物能够穿越血脑屏障（BBB）并在中枢神经系统发挥作用。这些结果使我们提出了新的线索，并得出结论，存在一个双烯酮基团可以支持更好的生物活性。
• Multiple 1,2,3-thiadiazoles
  作者：Mousa Al-Smadi、Norbert Hanold、Herbert Meier

  DOI：10.1002/jhet.5570340243

  日期：1997.3

  A series of compounds 3a-d,i-n with two or three 1,2,3-thiadiazole rings, useful for photocrosslinking processes, was prepared from the di- or triketones 1a-d,i-n via the corresponding hydrazones 2a-d,i-n by applying the Hurd-Mori method. A special synthetic sequence, 1e, 2e, 3e, 3f/3g, was elaborated for the olefinic system 3h.

  由二酮或三酮1a-d，in通过相应的hydr 2a-d，in制备了具有两个或三个1,2,3-噻二唑环的一系列化合物3a-d，可用于光交联过程。应用Hurd-Mori方法。为烯烃体系3h拟定了特殊的合成顺序1e，2e，3e，3f / 3g 。
• One-Pot Synthesis and Characterization of Some New Types of 5,5′-Disubstituted Bis(imidazolidine-2,4-diones)
  作者：Ziba Khodaee、Asieh Yahyazadeh、Nosrat O. Mahmoodi

  DOI：10.1002/jhet.1034

  日期：2013.3

  The synthesis and structural elucidation of some novel 5,5′‐disubstituted spiro and nonspiro‐bis‐hydantoins are reported. The Bucherer Burge's method has been modified for the preparation of some 5,5′‐substituted bis(imidazolidine‐2,4‐dione) derivatives starting with diketones (1–5) and dialdehydes (6, 7). In some cases, diastereoisomeric mixtures of compounds were obtained. The resulting bis‐hydantoins

  报道了一些新颖的5,5'-双取代螺和非螺-双-乙内酰脲的合成和结构解析。该布赫尔比尔格的方法已被修改为一些5,5'-取代的双（咪唑烷-2,4-二酮）开始二酮（衍生物的制备1-5）和二醛（6，7）。在某些情况下，获得化合物的非对映异构体混合物。得到的双乙内酰脲（8-11，13，14）都没有就我们所知，在文献中报道过。
• Prospective new amidinothiazoles as leukotriene B4 inhibitors
  作者：Ashraf A. Aly、Mahmoud A.A. Ibrahim、Essmat M. El-Sheref、Alaa M.A. Hassan、Alan B. Brown

  DOI：10.1016/j.molstruc.2018.07.085

  日期：2019.1

  Abstract An efficient and one-step synthesis of the versatile, hitherto new derivatives resembling LY293111, a prospective potent antagonist of the leukotriene B4 (LTB4) receptor, were reported. The strategy was based on the synthesis of an amidinothiazole ring, connected with phenoxy group. The synthesized compounds were structurally confirmed by IR, NMR (including 2D-NMR), mass spectra and elemental

  摘要 报道了一种高效的一步合成迄今为止类似于 LY293111 的多功能新衍生物，LY293111 是一种潜在的白三烯 B4 (LTB4) 受体的有效拮抗剂。该策略基于与苯氧基连接的脒基噻唑环的合成。合成的化合物也通过红外、核磁共振（包括二维核磁共振）、质谱和元素分析进行​​了结构确认。鉴定了 LTB4 受体的结合位点——即 BLT1 和 BLT2。对接结果表明，一些amidinobisthiazol-4-ones 对BLT1 和BLT2 受体具有有效的活性。
• Syntheses and Reactions of 4′-[(<i>ω</i>-Bromoalkyl)oxy]-and 4′,4′′′-(Polymethylenedoxy)-bis Substituted Chalcones
  作者：R. S. Sodani、Prakash C. Choudhary、Hari Om Sharma、B. L. Verma

  DOI：10.1155/2010/807059

  日期：——

  Base catalyzed condensation of 4-hydroxyacetophenone (1) with several aldehydes resulted 4′-hydroxychalcones (2a-c). Reaction ofα,ω-dibromoalkanes (3, n=2, 4 & 6) with (2a-c) in equimolar ratio resulted a mixture of 4′-[(ω-bromoalkyl)oxy]- substituted chalcones (4a-i) and 4′,4′′′-(polymethylenedioxy)-bis substituted chalcones (5a-i) separated by ethanol as soluble (4a-i) and insoluble (5a-i) products. Compounds (5a-i) were also synthesized by another route. Compound 1 on treatment with 3 in molar ratio 2:1 resulted 4′,4′′′-(polymethylenedioxy)-diacetophenone (4^#a-c) which on base catalyzed condensation gave compounds (5a-i). Reaction of 4d with substituted phenols and thiophenols gave corresponding phenoxy and thiophenoxy substituted chalcones (6a-f) where as compounds5a, 5b, 5d, 5h and 5eon treatment with hydrazine hydrate furnished corresponding bis-2-pyrazolines (7a-e). The structures of all synthesized compounds were confirmed on the basis of analytical and spectral data.

  4-羟基乙酰苯酮（1）与几种醛基催化的缩合反应产生了4'-羟基查尔酮（2a-c）。α,ω-二溴烷（3，n=2, 4和6）与（2a-c）在等摩尔比下反应产生了一种混合物，包括4'-[(ω-溴烷基)氧基]-取代查尔酮（4a-i）和4',4'''-(聚亚甲基二氧基)-双取代查尔酮（5a-i），通过乙醇分离为可溶性（4a-i）和不溶性（5a-i）产物。化合物（5a-i）也通过另一途径合成。化合物1与3以2:1的物质比反应生成4',4'''-(聚亚甲基二氧基)-二乙酰苯酮（4#a-c），在碱催化缩合反应中生成化合物（5a-i）。4d与取代苯酚和硫酚反应生成相应的苯氧基和硫酚氧基取代的查尔酮（6a-f），而化合物5a、5b、5d、5h和5e在与水合肼处理后产生相应的双-2-吡唑烯（7a-e）。所有合成化合物的结构均基于分析和光谱数据进行确认。