4-(allyloxy)-2-hydroxybenzaldehyde | 68287-22-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(allyloxy)-2-hydroxybenzaldehyde
• 英文别名: 2-hydroxy-4-prop-2-enoxybenzaldehyde
• CAS: 68287-22-9
• 化学式: C₁₀H₁₀O₃
• 分子量: 178.188
• InChiKey: ITQQJWLUOAEZNS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(allyloxy)-2-hydroxybenzaldehyde 在 palladium on activated charcoal 氢气 作用下， 生成 2,4-dihydroxy-3-propyl-benzaldehyde
  参考文献：
  名称：

  Hydroxyacetophenone-derived antagonists of the peptidoleukotrienes

  摘要：

  Considerations of the possible similarities between leukotriene D4 and its prototypical antagonist, FPL 55712, led to the development of a new series of leukotriene antagonists incorporating a hydroxyacetophenone group (e.g., the toluic acids 16 and 18). Although considerable attention has focused on FPL 55712-derived analogues, only limited investigations into alternatives for the standard 4-acetyl-3-hydroxy-2-propylphenoxy moiety have been reported. Therefore, an extensive study of modifications to the hydroxyacetophenone portion of toluic acid 18 was undertaken. Although no viable alternative to the 3-hydroxy moiety was discovered, replacements for the 2-propyl group (34, 37) and the 4-acetyl functionality (56, 59) yielded potent antagonists. A number of compounds exhibited longer duration of action in vivo than FPL 55712.

  DOI：

  10.1021/jm00124a014
• 作为产物：
  描述：

  4-Allyloxy-2-(3-methyl-but-2-enyloxy)-benzaldehyde 在 cerium(III) chloride 、 sodium iodide 作用下， 以 乙腈 为溶剂， 反应 4.0h， 以88%的产率得到4-(allyloxy)-2-hydroxybenzaldehyde
  参考文献：
  名称：

  氯化铈 (III)-NaI 对烷基芳基醚的温和化学选择性脱烷基化反应

  摘要：

  烷氧基苯甲醛中存在于羰基邻位的烷氧基以高产率选择性脱保护，而在中性反应条件下回流乙腈时，其他烷氧基不受氯化铈 (III)-NaI 影响。

  DOI：

  10.1246/cl.2000.738

文献信息

• Substituted phenyl compounds with a substituent having a thienyl ring
  申请人：Rhone-Poulenc Rorer Limited

  公开号：US06124343A1

  公开（公告）日：2000-09-26

  This invention is directed to compounds of formula I ##STR1## wherein R.sup.1 is CN, CH.sub.2 CN, CH.dbd.CHCN, CHO, or CH.dbd.CHCO.sub.2 H; R.sup.2 is aryl lower alkoxy, heteroaryl lower alkoxy, aryl lower alkylthio or heteroaryl lower alkylthio wherein each of the aryl and heteroaryl moieties is optionally substituted; R.sup.3 is halogen; R.sup.4 is optionally substituted aryl or optionally substituted heteroaryl; R.sup.5 is carboxy or an acid isostere; X is oxygen or sulphur; and n is zero or 1; or an N-oxide thereof, prodrug thereof solvate thereof, or pharmaceutically acceptable salt thereof, which compounds have endothelin antagonist activity. The invention is also directed to methods for preparing the compounds of formula I and their pharmaceutical use.

  这项发明涉及式I的化合物##STR1##其中R.sup.1为CN、CH.sub.2CN、CH.dbd.CHCN、CHO或CH.dbd.CHCO.sub.2H；R.sup.2为芳基低烷氧基、杂芳基低烷氧基、芳基低烷硫基或杂芳基低烷硫基，其中芳基和杂芳基中的每一个可选择地被取代；R.sup.3为卤素；R.sup.4为可选择地被取代的芳基或可选择地被取代的杂芳基；R.sup.5为羧基或酸异构体；X为氧或硫；n为零或1；或其N-氧化物、前药、溶剂化合物或药学上可接受的盐，这些化合物具有内皮素拮抗活性。该发明还涉及制备式I化合物及其药用的方法。
• Antidiabetic agents
  申请人：Merck & Co., Inc.

  公开号：US05859051A1

  公开（公告）日：1999-01-12

  The instant invention is concerned with acetylphenols which are useful as antiobesity and antidiabetic compounds. Compositions and methods for the use of the compounds in the treatment of diabetes and obesity and for lowering or modulating triglyceride levels and cholesterol levels or raising high density lipoprotein levels or for increasing gut motility or for treating atherosclerosis are also disclosed.

  该发明涉及乙酰苯酚，可用作抗肥胖和抗糖尿病化合物。还公开了在治疗糖尿病和肥胖中使用这些化合物的组合物和方法，以及降低或调节甘油三酯水平和胆固醇水平，或提高高密度脂蛋白水平，或增加肠道蠕动或治疗动脉粥样硬化的方法。
• Design, synthesis and docking study of 5-(substituted benzylidene)thiazolidine-2,4-dione derivatives as inhibitors of protein tyrosine phosphatase 1B
  作者：Zengtao Wang、Zhiguo Liu、Woojung Lee、Su-Nam Kim、Goo Yoon、Seung Hoon Cheon

  DOI：10.1016/j.bmcl.2014.05.099

  日期：2014.8

  A series of novel 5-(substituted benzylidene)thiazolidine-2,4-dione derivatives was designed, and synthesized based on our previous studies. Also their activities were evaluated as competitive inhibitors of protein tyrosine phosphatase 1B (PTP1B). Compounds 6d–6g, 7b, 7c, 7e, 7j, 7k, 7m, 14b and 14e–14f showed potent inhibitory effects against PTP1B, and compound 7e, the most potent among the series

  根据我们以前的研究，设计并合成了一系列新颖的5-（取代亚苄基）噻唑烷-2,4-二酮衍生物。还评估了它们的活性，将其作为蛋白酪氨酸磷酸酶1B（PTP1B）的竞争性抑制剂。化合物6d - 6g，7b，7c，7e，7j，7k，7m，14b和14e - 14f显示出对PTP1B的有效抑制作用，而化合物7e是该系列中最有效的，其IC 50为4.6μM。也是7e的Surflex-Dock对接模型被研究了。化合物7e在活性位点的负结合能为-7.35 kcal / mol，对PTP1B残基（Gly220，Ala217，Arg221，Asp181，Ser216，Cys215，Phe182，Gln262和Ile219）具有高亲和力，表明它可以稳定开放形式，并与PTP1B的催化位点产生更紧密的结合。
• Condensation of salicylaldehydes with ethyl 4,4,4-trichloro-3-oxobutanoate: a facile approach for the synthesis of substituted 2H-chromene-3-carboxylates
  作者：Mudulkar Sairam、Gannerla Saidachary、Bhimapaka China Raju

  DOI：10.1016/j.tetlet.2015.01.114

  日期：2015.3

  A highly efficient and simple protocol has been developed for the preparation of ethyl 2-oxo-2H-chromene-3-carboxylates 3a–v by the condensation of salicylaldehydes 1a–v with ethyl 4,4,4-trichloro-3-oxobutanoate 2 for the first time. The reaction is proceeding via Knoevenagel pathway followed by a selective addition of the phenolic hydroxyl group to the carbonyl group adjacent to the CCl3 group rather

  通过将水杨醛1a - v与4,4,4-三氯-3-氧代丁酸乙酯缩合，已开发出一种高效且简单的方案，用于制备2-oxo-2 H-色烯-3-羧酸乙酯3a – v第一次2。该反应通过Knoevenagel途径进行，随后由于强的电子吸收作用，将酚羟基选择性地添加到与CCl 3基团相邻的羰基上而不是酯羰基上，并且生成了香豆素衍生物3a，消除了CHCl 3。
• Molecular modeling and snake venom phospholipase A 2 inhibition by phenolic compounds: Structure–activity relationship
  作者：Md. Iqbal Alam、Mohammed A. Alam、Ozair Alam、Amit Nargotra、Subhash Chandra Taneja、Surrinder Koul

  DOI：10.1016/j.ejmech.2016.03.008

  日期：2016.5

  In our earlier study, we have reported that a phenolic compound 2-hydroxy-4-methoxybenzaldehyde from Janakia arayalpatra root extract was active against Viper and Cobra envenomations. Based on the structure of this natural product, libraries of synthetic structurally variant phenolic compounds were studied through molecular docking on the venom protein. To validate the activity of eight selected compounds

  在我们较早的研究中，我们报道了来自Janakia arayalpatra根提取物的酚类化合物2-羟基-4-甲氧基苯甲醛具有抗蛇蝎毒和眼镜蛇毒的活性。基于这种天然产物的结构，通过分子对接在毒蛋白上，研究了合成的结构变异酚类化合物的文库。为了验证八个选定化合物的活性，我们已经在体内和体外模型中对其进行了测试。发现化合物21（ 2-羟基-3-甲氧基苯甲醛），22（2-羟基-4-甲氧基苯甲醛）和35（2-羟基-3-甲氧基苄醇）对毒液诱导的病理生理变化具有活性。化合物20，15和35显示的最大抗出血，抗致死和PLA 2分别抑制活性。就SAR而言，甲酰基与酚基的结合被认为是增加抗蛇毒素活性的重要因素。上述观察结果证实了酚类化合物的抗毒活性，这需要进一步研究以开发新的抗蛇毒引线。