ethyl 2-(4-(2-aminoethyl)phenoxy)acetate | 72131-30-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl 2-(4-(2-aminoethyl)phenoxy)acetate
• 英文别名: ethyl 4-(2-aminoethyl)-phenoxyacetate；ethyl 4-(2-aminoethyl)phenoxyacetate；4-(2-Aminoethyl)-phenoxyessigsaeureethylester；Acetic acid, 2-[4-(2-aminoethyl)phenoxy]-, ethyl ester；ethyl 2-[4-(2-aminoethyl)phenoxy]acetate
• CAS: 72131-30-7
• 化学式: C₁₂H₁₇NO₃
• mdl: MFCD09047512
• 分子量: 223.272
• InChiKey: MEEXXWXSOPKRTC-UHFFFAOYSA-N

物化性质

• 沸点：
  335.9±22.0 °C(Predicted)
• 密度：
  1.100±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.416
• 拓扑面积：
  61.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 2-(4-(2-aminoethyl)phenoxy)acetate 在 硼烷四氢呋喃络合物 、 碳酸氢钠 、 1-羟基苯并三唑 、 三乙胺 、 sodium hydroxide 、 N,N'-二异丙基碳二亚胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 38.5h， 生成 sodium 2-(4-{2-[N-(heptyl)-N-(benzoxazol-2-yl)amino]ethyl}phenoxy)ethanoate
  参考文献：
  名称：

  Synthesis, Characterization and Biological Evaluation of Ureidofibrate-Like Derivatives Endowed with Peroxisome Proliferator-Activated Receptor Activity

  摘要：

  A series of ureidofibrate-like derivatives was prepared and assayed for their PPAR functional activity. A calorimetric approach was used to characterize PPAR gamma-ligand interactions, and docking experiments and X-ray studies were performed to explain the observed potency and efficacy. R-1 and S-1 were selected to evaluate several aspects of their biological activity. In an adipogenic assay, both enantiomers increased the expression of PPAR gamma target genes and promoted the differentiation of 3T3-L1 fibroblasts to adipocytes. In vivo administration of these compounds to insulin resistant C57Bl/6J mice fed a high fat diet reduced visceral fat content and body weight. Examination of different metabolic parameters showed that R-1 and S-1 are insulin sensitizers. Notably, they also enhanced the expression of hepatic PPAR alpha target genes indicating that their in vivo effects stemmed from an activation of both PPAR alpha and gamma. Finally, the capability of R-1 and S-1 to inhibit cellular proliferation in colon cancer cell lines was also evaluated.

  DOI：

  10.1021/jm201306q
• 作为产物：
  描述：

  酪胺盐酸盐 在 palladium 10% on activated carbon 、 氢气 、 sodium hydride 、 potassium carbonate 作用下， 以 乙醚 、 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 20.0 ℃ 、506.66 kPa 条件下， 反应 30.0h， 生成 ethyl 2-(4-(2-aminoethyl)phenoxy)acetate
  参考文献：
  名称：

  Synthesis, Characterization and Biological Evaluation of Ureidofibrate-Like Derivatives Endowed with Peroxisome Proliferator-Activated Receptor Activity

  摘要：

  A series of ureidofibrate-like derivatives was prepared and assayed for their PPAR functional activity. A calorimetric approach was used to characterize PPAR gamma-ligand interactions, and docking experiments and X-ray studies were performed to explain the observed potency and efficacy. R-1 and S-1 were selected to evaluate several aspects of their biological activity. In an adipogenic assay, both enantiomers increased the expression of PPAR gamma target genes and promoted the differentiation of 3T3-L1 fibroblasts to adipocytes. In vivo administration of these compounds to insulin resistant C57Bl/6J mice fed a high fat diet reduced visceral fat content and body weight. Examination of different metabolic parameters showed that R-1 and S-1 are insulin sensitizers. Notably, they also enhanced the expression of hepatic PPAR alpha target genes indicating that their in vivo effects stemmed from an activation of both PPAR alpha and gamma. Finally, the capability of R-1 and S-1 to inhibit cellular proliferation in colon cancer cell lines was also evaluated.

  DOI：

  10.1021/jm201306q

文献信息

• Dihydropyridine Lactam Analogs Targeting BET Bromodomains
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  DOI：10.1002/cmdc.202100407

  日期：2022.1.5

  Selectivity you can BET on: Analogs of previously reported lactam 6 with different linker lengths and linker types were found to be highly selective for BET bromodomains, and generally more selective for the first (BD1) and second (BD2) bromodomains of BRD4 rather than for those of BRDT.

  您可以打赌的选择性：发现先前报道的具有不同接头长度和接头类型的内酰胺6的类似物对 BET 溴结构域具有高度选择性，并且通常对 BRD4 的第一个 (BD1) 和第二个 (BD2) 溴结构域更具选择性，而不是对BRDT的那些。
• Synthesis and Pharmacological Evaluation of Dual Acting Ligands Targeting the Adenosine A_2A and Dopamine D₂ Receptors for the Potential Treatment of Parkinson’s Disease
  作者：Manuela Jörg、Lauren T. May、Frankie S. Mak、Kiew Ching K. Lee、Neil D. Miller、Peter J. Scammells、Ben Capuano

  DOI：10.1021/jm501254d

  日期：2015.1.22

  series of more integrated and “drug-like” dual acting molecules, incorporating ropinirole as a dopamine D2 receptor agonist and ZM 241385 as an adenosine A2A receptor antagonist. The best compounds of our series maintained the potency of the original pharmacophores at both receptors (adenosine A2A and dopamine D2). In addition, the integrated dual acting ligands also showed promising results in preliminary

  药物发现中相对较新的策略是双作用配体的开发。这些分子潜在地能够同时在异二聚体的两个正构结合位点相互作用，可能导致增强的亚型选择性，更高的亲和力，增强或改变的生理反应，以及减少对多种药物给药方案的依赖。在这项研究中，我们成功合成了一系列经典的异二价配体以及一系列更加整合和“类药物”双作用分子，其中纳入了罗匹尼罗作为多巴胺D 2受体激动剂和ZM 241385作为腺苷A 2A受体拮抗剂。我们系列中最好的化合物在两个受体上都保持了原始药效基团的效力（腺苷A2A和多巴胺D 2）。此外，整合的双重作用配体在初步的血脑屏障通透性测试中也显示出令人鼓舞的结果，而经典的异二价配体可能更适合用作药理学工具。
• Phenoxyalkylcarboxylic acid compounds and thrombocyte-aggregation
  申请人：Boehringer Mannheim GmbH

  公开号：US04258058A1

  公开（公告）日：1981-03-24

  Phenoxyalkylcarboxylic acid compounds of the formula ##STR1## wherein R is hydrogen or lower alkyl R.sub.1 is alkyl or aryl, aralkyl or aralkenyl radical, the aryl moiety of which can be substituted one or more times by halogen, hydroxyl, trifluoromethyl or lower alkyl, alkoxy or acyl R.sub.2 and R.sub.3 are individually selected from hydrogen or lower alkyl, and n is 0, 1, 2 or 3 and the physiologically acceptable salts, esters and amides thereof; are outstandingly effective in inhibiting thrombocyte aggregation.

  该公式中的Phenoxyalkylcarboxylic酸化合物，其中R是氢或较低的烷基，R.sub.1是烷基或芳基，芳基可以被卤素、羟基、三氟甲基或较低的烷基、烷氧基或酰基取代一次或多次，R.sub.2和R.sub.3分别选自氢或较低的烷基，n为0、1、2或3，其生理上可接受的盐、酯和酰胺在抑制血小板聚集方面具有出色的效果。
• Compound with platelet aggregation inhibitor activity
  申请人：Meiji Seika Kabushiki Kaisha

  公开号：US05594004A1

  公开（公告）日：1997-01-14

  A compound represented by the general formula (I) and a pharmaceutically acceptable salt and solvate thereof having an effect for inhibiting the agglutination of platelets is disclosed: ##STR1## wherein R.sup.1 represents a group --W--(CH.sub.2).sub.i --COOR.sup.3, R.sup.2 represents a hydrogen atom or a group --W--(CH.sub.2).sub.i --COOR.sup.3 or --OR.sup.4, X represents --CH.dbd. or --N.dbd., Y represents (i) a group --(CO).sub.k --N(R.sup.5)--Z--, wherein Z represents a bond or a group --(CH.sub.2).sub.m --CO-- or a group --(CH.sub.2).sub.m --CHR.sup.6 --, (ii) a group --(CH.sub.2).sub.m --N(R.sup.5)--(CO).sub.k --, or (iii) a group --(CO).sub.k -Het, wherein Het represents a five- or six-membered heterocyclic ring comprising a nitrogen atom, A represents (i) the following groups (III) or (IV) ##STR2## B represents a bond, C.sub.1-6 alkylene or C.sub.2-6 alkenylen.

  公开了一种由通式(I)表示的化合物及其药学上可接受的盐和溶剂，具有抑制血小板凝聚作用的效果：##STR1## 其中R.sup.1代表一个基团--W--(CH.sub.2).sub.i --COOR.sup.3，R.sup.2代表氢原子或一个基团--W--(CH.sub.2).sub.i --COOR.sup.3或--OR.sup.4，X代表--CH.dbd.或--N.dbd.，Y代表(i)一个基团--(CO).sub.k--N(R.sup.5)--Z--，其中Z代表一个键或一个基团--(CH.sub.2).sub.m --CO--或一个基团--(CH.sub.2).sub.m --CHR.sup.6--，(ii)一个基团--(CH.sub.2).sub.m --N(R.sup.5)--(CO).sub.k--，或(iii)一个基团--(CO).sub.k-Het，其中Het代表一个含氮原子的五元或六元杂环，A代表(i)以下基团(III)或(IV)##STR2## B代表一个键，C.sub.1-6烷基或C.sub.2-6烯基。
• Potent inhibitors of Huntingtin protein aggregation in a cell-based assay
  作者：Alison Rinderspacher、Maria Laura Cremona、Yidong Liu、Shi-Xian Deng、Yuli Xie、Gangli Gong、Nathalie Aulner、Udo Többen、Katherine Myers、Caty Chung、Monique Andersen、Dušica Vidović、Stephan Schürer、Lars Brandén、Ai Yamamoto、Donald W. Landry

  DOI：10.1016/j.bmcl.2009.01.087

  日期：2009.3

  A quinazoline that decreases polyglutamine aggregate burden in a cell-based assay was identified from a high-throughput screen of a chemical-compound library, provided by the NIH Molecular Libraries Small Molecule Repository (MLSMR). A structure and activity study yielded leads with submicromolar potency. (C) 2009 Elsevier Ltd. All rights reserved.