2-(5-溴苯并呋喃-3-基)乙酸乙酯 | 200204-85-9

• 物质功能分类: 分析化学 - 标准品 - 药典标准品和杂质标准品
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 中文名称: 2-(5-溴苯并呋喃-3-基)乙酸乙酯
• 中文别名: 5-溴-3-苯并呋喃乙酸乙酯
• 英文名称: (5-Bromobenzofuran-3-yl)acetic acid ethyl ester
• 英文别名: Ethyl 2-(5-bromobenzofuran-3-yl)acetate；ethyl 2-(5-bromo-1-benzofuran-3-yl)acetate
• CAS: 200204-85-9
• 化学式: C₁₂H₁₁BrO₃
• 分子量: 283.122
• InChiKey: NWCIURORZMAWNA-UHFFFAOYSA-N

物化性质

• 沸点：
  341.7±27.0 °C(Predicted)
• 密度：
  1.475±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  39.4
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2932999099
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

制备方法与用途

2-（5-溴苯并呋喃-3-基）乙酸乙酯可作为有机合成中间体和医药中间体，广泛应用于实验室研发和化工生产过程。

反应信息

• 作为反应物：
  描述：

  2-(5-溴苯并呋喃-3-基)乙酸乙酯 在 氨 作用下， 反应 48.0h， 生成 2-(5-bromobenzofuran-3-yl)acetamide
  参考文献：
  名称：

  Structure-Based Design Leads to the Identification of Lithium Mimetics That Block Mania-like Effects in Rodents. Possible New GSK-3β Therapies for Bipolar Disorders

  摘要：

  More than two million American adults, or approximately one percent of the population 18 years or older, suffer from bipolar disorder. Current treatments include the so-called "mood stabilizers," lithium and valproic acid. Both are relatively dated drugs that are only partially effective and produce various undesirable side effects including weight gain. Based upon continued efforts to understand the molecular target for lithium, it now appears that specific inhibitors of the enzyme glycogen synthase kinase-3 beta (GSK-3 beta) may mimic the therapeutic action of mood stabilizers and might therefore allow for the design of improved drugs for treating patients with bipolar disorder as well as certain neurodegenerative disorders. Furthermore, the pro-apoptotic properties of the GSK-3 enzyme suggest the possible use of such inhibitors as neuroprotective agents. In fact, neuroprotection may contribute to the treatment of mood disorders. The present chemistry, modeling, and biology efforts have identified 3-benzofuranyl-4-indolylmaleimides as potent and relatively selective GSK-3 beta inhibitors. The best ligand in this series (having a K-i value of 4.6 nM against GSK-3 beta) was studied in a novel mouse model of mania that has recently been validated with several clinically effective mood stabilizers. This study presents the first demonstration of the efficacy of a GSK-3 beta inhibitor in this mouse model of mania. Selective brain penetrable GSK-3 ligands like those described herein become valuable research tools in better defining the role of this multifaceted kinase in both physiological and pathophysiological events.

  DOI：

  10.1021/ja068969w
• 作为产物：
  描述：

  1-(5-溴-2-羟基苯基)-2-氯乙酮 在 sodium acetate 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 24.0h， 生成 2-(5-溴苯并呋喃-3-基)乙酸乙酯
  参考文献：
  名称：

  Structure-Based Design Leads to the Identification of Lithium Mimetics That Block Mania-like Effects in Rodents. Possible New GSK-3β Therapies for Bipolar Disorders

  摘要：

  More than two million American adults, or approximately one percent of the population 18 years or older, suffer from bipolar disorder. Current treatments include the so-called "mood stabilizers," lithium and valproic acid. Both are relatively dated drugs that are only partially effective and produce various undesirable side effects including weight gain. Based upon continued efforts to understand the molecular target for lithium, it now appears that specific inhibitors of the enzyme glycogen synthase kinase-3 beta (GSK-3 beta) may mimic the therapeutic action of mood stabilizers and might therefore allow for the design of improved drugs for treating patients with bipolar disorder as well as certain neurodegenerative disorders. Furthermore, the pro-apoptotic properties of the GSK-3 enzyme suggest the possible use of such inhibitors as neuroprotective agents. In fact, neuroprotection may contribute to the treatment of mood disorders. The present chemistry, modeling, and biology efforts have identified 3-benzofuranyl-4-indolylmaleimides as potent and relatively selective GSK-3 beta inhibitors. The best ligand in this series (having a K-i value of 4.6 nM against GSK-3 beta) was studied in a novel mouse model of mania that has recently been validated with several clinically effective mood stabilizers. This study presents the first demonstration of the efficacy of a GSK-3 beta inhibitor in this mouse model of mania. Selective brain penetrable GSK-3 ligands like those described herein become valuable research tools in better defining the role of this multifaceted kinase in both physiological and pathophysiological events.

  DOI：

  10.1021/ja068969w
• 作为试剂：
  描述：

  、 双(三甲基硅烷基)氨基钾 、 、 5-溴-3-苯并呋喃酮 、 氯化铵 、 乙酸乙酯 在 2-(5-溴苯并呋喃-3-基)乙酸乙酯 、 silica 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 19.0h， 以(5-Bromobenzofuran-3-yl)acetic acid ethyl ester was obtained as a low melting solid (4.2 g, 57%), mp 38-40° C的产率得到2-(5-溴苯并呋喃-3-基)乙酸乙酯
  参考文献：
  名称：

  Azetidine, pyrrolidine and piperidine derivatives as 5-HT.sub.1D

  摘要：

  式I的一类取代的氮杂环化合物，包括氮杂环丙烷、吡咯烷和哌嗪衍生物，是5-HT.sub.1-样受体的选择性激动剂，是人类5-HT.sub.1D.alpha.受体亚型的有效激动剂，同时相对于5-HT.sub.1D.beta.亚型具有至少10倍的选择性亲和力；因此，在治疗和/或预防临床病症方面，特别是偏头痛和相关疾病方面，这些化合物是有用的，因为这些病症需要5-HT.sub.1D受体的亚型选择性激动剂，而相对于非亚型选择性的5-HT.sub.1D受体激动剂，这些化合物引起的副作用较少，尤其是不良心血管事件。 ##STR1##

  公开号：

  US06127388A1

文献信息

• Synthesis and Preliminary Evaluation of Benzofuran-Oxadiazole Conjugates as Potential Antitubercular Agents
  作者：Veerabhadrayya S. Negalurmath、Obelannavar Kotresh、Mahantesha Basanagouda

  DOI：10.14233/ajchem.2019.21831

  日期：2019.3

  the compounds were screened for preliminary antitubercular activity against Mycobacterium phlei and Mycobacterium tuberculosis H37RV. Among all the target compounds, the compound possessing chlorine (7k, MIC 1.56 μg/mL) and bromine (7m, MIC 1.56 μg/mL) on 6th position of benzofuran showed highest activity against Mycobacterium phlei. Whereas, bromine on either 5th position (7l, MIC 3.125 μg/mL) or 6th

  在本研究中，设计、合成了一系列苯并呋喃-恶二唑缀合物7(ao)，并通过IR、1H NMR、13C NMR和质谱数据进行表征。所有化合物均针对草分枝杆菌和结核分枝杆菌 H37RV 的初步抗结核活性进行了筛选。在所有目标化合物中，苯并呋喃6位上具有氯（7k，MIC 1.56 μg/mL）和溴（7m，MIC 1.56 μg/mL）的化合物对草分枝杆菌表现出最高的活性。而苯并呋喃上第 5 位（7l，MIC 3.125 μg/mL）或第 6 位（7m MIC 3.125 μg/mL）上的溴对结核分枝杆菌 (H37 RV) 表现出最高活性。
• Piperazine, piperidine and tetrahydropyridine derivatives as 5-HT
  申请人：Merck Sharp & Dohme Ltd.

  公开号：US05998416A1

  公开（公告）日：1999-12-07

  A class of N-substituted piperazine, piperidine, and tetrahydropyridine derivatives, further subltitutedat the 4-position by an optionally substituted alkenyl, alkynyl, aryl-alkyl or heteroaryl-alkyl moiety, are selective agonists of 5-HT.sub.1 -like receptors, being potent agonists of the human 5-HT.sub.1D.alpha. receptor subtype whilst possessing at least a 10-fold selective affinity for the 5-HT.sub.1D.alpha. receptor subtype relative to the 5-HT.sub.1D.beta. subtype; they are therefore useful in the treatment and/or prevention of clinical conditions, in particular migraine and associated disorders, for which a subtype-selective agonist of 5-HT.sub.1D receptors is indicated, whilst eliciting fewer side-effects, notably adverse cardiovascular events, than those associated with non-subtype-selective 5-HT.sub.1D receptor agonists.

  一类N-取代哌嗪、哌啶和四氢吡啶衍生物，进一步在4位被一个可选取代的烯基、炔基、芳基-烷基或杂环芳基-烷基基团取代，是5-HT.sub.1-类受体的选择性激动剂，是人类5-HT.sub.1D.alpha.受体亚型的有效激动剂，同时相对于5-HT.sub.1D.beta.亚型具有至少10倍的选择性亲和力；因此，在治疗和/或预防临床疾病，特别是偏头痛和相关疾病方面，需要5-HT.sub.1D受体亚型选择性激动剂，同时产生的副作用较少，特别是不良心血管事件，比非亚型选择性5-HT.sub.1D受体激动剂更少。
• LYSOPHOSPHATIDIC ACID RECEPTOR ANTAGONISTS
  申请人：InterMune, Inc.

  公开号：US20140213538A1

  公开（公告）日：2014-07-31

  Compounds, methods of making such compounds, pharmaceutical compositions and medicaments comprising such compounds, and methods of using such compounds to treat, prevent or diagnose diseases, disorders, or conditions associated with one or more of the lysophosphatidic acid receptors are provided.

  本发明提供了化合物、制备这种化合物的方法、包含这种化合物的制药组合物和药物，以及使用这种化合物治疗、预防或诊断与一种或多种溶血磷脂酸受体相关的疾病、疾病、或病况的方法。
• BICYCLIC COMPOUND THAT ACTS AS CRBN PROTEIN REGULATOR
  申请人：Medshine Discovery Inc.

  公开号：EP4043455A1

  公开（公告）日：2022-08-17

  A compound represented by formula (III) or a pharmaceutically acceptable salt thereof, and disclosed is an application thereof in the preparation of a medication for treating diseases related to a CRBN receptor.

  公式（III）所代表的化合物或其药学上可接受的盐，并且公开了其在制备治疗与CRBN受体相关的疾病的药物中的应用。
• [EN] FURAN FUSED RING-SUBSTITUTED GLUTARIMIDE COMPOUND<br/>[FR] COMPOSÉ DE GLUTARIMIDE SUBSTITUÉ PAR UN CYCLE FUSIONNÉ À UN FURANE<br/>[ZH] 呋喃稠环取代的戊二酰亚胺类化合物
  申请人：MEDSHINE DISCOVERY INC

  公开号：WO2022194221A1

  公开（公告）日：2022-09-22

  本发明公开了一系列呋喃稠环取代的戊二酰亚胺类化合物，及其在制备治疗相关疾病药物中的应用，具体公开了式(II)所示化合物及其药学上可接受的盐。