4-(3-甲氧基苯基)-3-氧丁酸乙酯 | 324570-26-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 4-(3-甲氧基苯基)-3-氧丁酸乙酯
• 英文名称: ethyl 4-(3-methoxyphenyl)-3-oxobutanoate
• CAS: 324570-26-5
• 化学式: C₁₃H₁₆O₄
• 分子量: 236.268
• InChiKey: KBNNDJXTUQSJOF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 危险性防范说明：
  P261,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H315,H319

反应信息

• 作为反应物：
  描述：

  4-(3-甲氧基苯基)-3-氧丁酸乙酯 在 ammonium acetate 、 溶剂黄146 作用下， 以 甲苯 为溶剂， 反应 6.0h， 以86%的产率得到ethyl (2Z)-3-amino-4-(3-methoxyphenyl)but-2-enoate
  参考文献：
  名称：

  Structural Optimization and Biological Evaluation of 2-Substituted 5-Hydroxyindole-3-carboxylates as Potent Inhibitors of Human 5-Lipoxygenase

  摘要：

  Pharmacological suppression of leukotriene biosynthesis by inhibitors of 5-lipoxygenase (5-LO) is a strategy to intervene with inflammatory and allergic disorders. We recently presented 2-amino-5-hydroxy-1H-indoles as efficient 5-LO inhibitors in cell-based and cell-free assays. Structural optimization led to novel benzo[g]indole-3-carboxylates exemplified by ethyl 2-(3-chlorobenzyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate (compound 11a), which inhibits 5-LO activity in human neutrophils and recombinant human 5-LO with IC50 values of 0.23 and 0.086 mu M, respectively. Notably, 11a efficiently blocks 5-LO product formation in human whole blood assays (IC50 = 0.83-1.6 mu M) and significantly prevented leukotriene B-4 production in pleural exudates of carrageenan-treated rats, associated with reduced severity of pleurisy. Together, on the basis of their high potency against 5-LO and the marked efficacy in biological systems, these novel and straightforward benzo[g]indole-3-carboxylates may have potential as anti-inflammatory therapeutics.

  DOI：

  10.1021/jm900212y
• 作为产物：
  描述：

  3-甲氧基苯基乙酰氯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 4.5h， 生成 4-(3-甲氧基苯基)-3-氧丁酸乙酯
  参考文献：
  名称：

  DNA−Protein Cross-Linking:  Model Systems for Pyrimidine−Aromatic Amino Acid Cross-Linking

  摘要：

  We have synthesized simple model systems to explore the possibility of photo-cross-linking between the pyrimidine bases and the side chains of the aromatic amino acids. Thymine/phenylalanine and thymine/tyrosine models gave cross-links, and thymine/tryptophan models gave complex mixtures; the cytosine/phenylalanine model was unreactive. The quantum yields for the model cross-linking reactions were 18-46 times smaller than those for thymine dimer formation. Biphotonic excitation contributes little to the yield of these reactions.

  DOI：

  10.1021/ol052876m

文献信息

• [EN] COMPOUNDS AND USE THEREOF IN THE EXPANSION OF HEMATOPOIETIC STEM CELLS AND/OR HEMATOPOIETIC PROGENITOR CELLS<br/>[FR] COMPOSÉS ET LEUR UTILISATION DANS L'EXPANSION DE CELLULES SOUCHES HÉMATOPOÏÉTIQUES ET/OU CELLULES PROGÉNITRICES HÉMATOPOÏÉTIQUES
  申请人：UNIV MONTREAL

  公开号：WO2015161373A1

  公开（公告）日：2015-10-29

  Compounds of general formula or salts or prodrugs thereof, are provided and described herein. The compounds are useful to expand hematopoietic stem cell and/or hematopoietic progenitor cell populations. Particularly, the hematopoietic cells are human cells. The compounds are also useful in the medical treatment of hematopoietic disorder/malignancy, an autoimmune disease and/or an inherited immune-deficient disease in a subject.

  本文提供并描述了一般式化合物、盐或其前药。这些化合物对于扩增造血干细胞和/或造血祖细胞群体是有用的。特别地，这些造血细胞是人类细胞。这些化合物还可用于治疗受试者的造血障碍/恶性肿瘤、自身免疫疾病和/或遗传性免疫缺陷疾病。
• Triaryl-Substituted Divinyl Ketones Cyclization: Nazarov Reaction versus Friedel–Crafts Electrophilic Substitution
  作者：Valerii Z. Shirinian、Andrey G. Lvov、Anton V. Yadykov、Liana V. Yaminova、Vadim V. Kachala、Ashot I. Markosyan

  DOI：10.1021/acs.orglett.6b03023

  日期：2016.12.16

  triaryl-substituted divinyl ketones has been studied. It was found that the reaction pathway strongly depends on the nature of the aryl substituent at the α-position to the carbonyl group. An electron-rich aromatic substituent promotes the reaction to proceed through the intramolecular Friedel–Crafts electrophilic substitution giving dihydronaphthalene derivatives. In contrast, the presence of an electron-deficient

  已经研究了广泛的三芳基取代的二乙烯基酮的酸催化环化。发现反应路径强烈取决于羰基的α位上的芳基取代基的性质。富电子的芳族取代基通过分子内的Friedel-Crafts亲电取代促进反应进行，从而生成二氢萘衍生物。相反，缺电子取代基的存在有利于Nazarov4π-旋转环化，产生三芳基取代的环戊烯酮。亲电取代反应应用于噻吩和噻唑衍生物。
• Cyclization of Polarized Divinyl Ketones under Aqueous and Ambient Conditions
  作者：Anton V. Yadykov、Liana V. Yaminova、Mikhail M. Krayushkin、Valerii Z. Shirinian

  DOI：10.1002/adsc.202000956

  日期：2021.1.5

  applicability on a gram‐scale. It was shown that the amphiphilicity of the substrate and a low energy barrier of the reaction are a prerequisite for electrophilic and concerted reactions under aqueous and ambient conditions.

  已经开发了一种“水上”方案，用于通过使用盐酸作为促进剂，使极化的三芳基二乙烯基酮环化，以45-95％的产率合成康维他汀A-4（CA-4）类似物。由于在环境温度下进行超声波照射，反应时间减少了约30倍。这种新方法的其他优点是操作简便，易于操作，无需色谱柱纯化以及适用于克级。结果表明，在水和环境条件下，底物的两亲性和反应的低能垒是亲电和协同反应的先决条件。
• Acylation of Meldrum’s acid with arylacetic acid imidazolides as a convenient method for the synthesis of 4-aryl-3-oxobutanoates
  作者：A. A. Shimkin、V. Z. Shirinian、A. K. Mailian、D. V. Lonshakov、V. V. Gorokhov、M. M. Krayushkin

  DOI：10.1007/s11172-011-0019-9

  日期：2011.1

  C-Acylation of Meldrum’s acid by (het)arylacetic acids in ethanol in the presence of 1,1′-carbonyldiimidazole leads to ethyl 4-(het)aryl-3-oxobutanoates in high yields.

  在 1,1′-羰基二咪唑存在下，(庚)芳基乙酸在乙醇中对 Meldrum's 酸进行 C-酰化，可高产 4-(庚)芳基-3-氧代丁酸乙酯。
• [DE] VERWENDUNG VON INDOL-3-CARBONSÄUREESTERN ZUR HEMMUNG DER MIKROSOMALEN PROSTAGLANDIN E2 SYNTHASE<br/>[EN] USE OF INDOLE-3-CARBOXYLIC ESTERS FOR INHIBITING MICROSOMAL PROSTAGLANDIN E2 SYNTHASE<br/>[FR] UTILISATION D'ESTERS DE L'ACIDE INDOL-3-CARBOXYLIQUE POUR L'INHIBITION DE LA PROSTAGLANDINE E2 SYNTHASE MICROSOMALE
  申请人：UNIV TUEBINGEN

  公开号：WO2009146696A1

  公开（公告）日：2009-12-10

  Die vorliegende Erfindung betrifft die Verwendung von lndol-3-carbonsäureestern und seiner Derivate zur Hemmung der induzierbaren mikrosomalen Prostaglandin E2 Synthase-1 und/oder zur Hemmung der 5-Lipoxygenase. Insbesondere betrifft die Erfindung die Verwendung von Derivaten des 3-Carboxy-aryl[g]indols, vor allem von 2-Aryl- und 2-Arylalkyl-Aryl[g]indol-3-carbonsäureestern sowie deren strukturellen Abkömmlingen zur Hemmung der induzierbaren mikrosomalen Prostaglandin E2 Synthase-1 und / oder zur Hemmung der 5-Lipoxygenase. Ferner betrifft die Erfindung die Verwendung von lndol-3-carbonsäureestern zur Herstellung eines Arzneimittels zur Behandlung von PGE2- und / oder 5-LO-vermittelter Erkrankungen und krankhafter Zustände, insbesondere von entzündlichen chronischen Entzündungen wie rheumatoide Arthritis, Osteoarthritis, Erkrankungen des kardiovaskulären Systems, Asthma, allergische Rhinitis, Multiple Sklerose, entzündliche Hauterkrankungen, Osteoporose und Krebs, Schmerz und Fieber, bei denen PGE2 und / oder 5-LO Produkte eine Rolle spielen.

  本发明涉及使用indol-3-羧酸酯及其衍生物来抑制可诱导的微粒体前列腺素E2合成酶-1和/或抑制5-脂氧合酶。具体涉及使用3-羧基芳基[g]吲哚的衍生物，特别是2-芳基和2-芳基烷基芳基[g]吲哚-3-羧酸酯及其结构衍生物来抑制可诱导的微粒体前列腺素E2合成酶-1和/或抑制5-脂氧合酶。此外，本发明涉及使用indol-3-羧酸酯来制备药物，用于治疗PGE2和/或5-LO介导的疾病和病态，特别是慢性炎症性疾病，如类风湿性关节炎，骨关节炎，心血管系统疾病，哮喘，过敏性鼻炎，多发性硬化症，炎性皮肤病，骨质疏松症和癌症，以及疼痛和发热，在其中PGE2和/或5-LO产物发挥作用。