5-溴-2-甲基-3-吲哚乙酸乙酯 | 72016-68-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 中文名称: 5-溴-2-甲基-3-吲哚乙酸乙酯
• 英文名称: 5-bromo-2-methyl-1H-indole-3-acetic acid ethyl ester
• 英文别名: (5-bromo-2-methyl-1H-indol-3-yl)acetic acid ethyl ester；ethyl 2-(5-bromo-2-methyl-1H-indol-3-yl)acetate；ethyl (5-bromo-2-methyl-1H-indol-3-yl)acetate；ethyl (5-bromo-2-methylindol-3-yl)acetate；ethyl-5-bromo-2-methyl-3-indoleacetate；(5-bromo-2-methyl-indol-3-yl)-acetic acid ethyl ester
• CAS: 72016-68-3
• 化学式: C₁₃H₁₄BrNO₂
• 分子量: 296.164
• InChiKey: GNAIWTYKMSIQQR-UHFFFAOYSA-N

物化性质

• 熔点：
  96-98 °C
• 沸点：
  414.6±40.0 °C(Predicted)
• 密度：
  1.454±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  42.1
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H302,H317

反应信息

• 作为反应物：
  描述：

  5-溴-2-甲基-3-吲哚乙酸乙酯 在 lithium aluminium tetrahydride 、 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 2-[5-bromo-1-(diphenylmethyl)-2-methyl-1H-indol-3-yl]ethanol
  参考文献：
  名称：

  Inhibition of Cytosolic Phospholipase A₂α: Hit to Lead Optimization

  摘要：

  Compound I was previously reported to be a potent inhibitor of cPLA,(x in both artificial monomeric substrate and cell-based assays. However, I was inactive in whole blood assays previously used to characterize cyclooxygenase and lipoxygenase inhibitors. The IC(50) of 1 increased dramatically with cell number or lipid/detergent concentration. In an attempt to insert an electrophilic ketone between the indole and benzoic acid moieties, we discovered that increasing the distance between the two moieties gave a compound with activity in the GLU (7-hydroxycoumarinyl-gamma-linolenate) micelle assay, which contains lipid and detergent. Extensive structure-activity relationship work around this lead identified a potent pharmacophore for cPLA a inhibition. The IC(50)s between the GLU micelle and rat whole blood assays correlated highly. No correlation was found for other parameters, including lipophilicity or acidity of the required acid functionality. Compounds 25, 39, and 94 emerged as potent, selective inhibitors of cPLA(2)alpha and represent well-validated starting points for further optimization.

  DOI：

  10.1021/jm0507882
• 作为产物：
  描述：

  乙酰丙酸乙酯 在 乙醇 作用下， 生成 5-溴-2-甲基-3-吲哚乙酸乙酯
  参考文献：
  名称：

  Amorosa; Lipparini, Annali di Chimica, 1957, vol. 47, p. 722,725

  摘要：

  DOI：

文献信息

• Hypoglycemic imidazoline compounds
  申请人：ELI LILLY AND COMPANY

  公开号：EP1266897A3

  公开（公告）日：2003-12-03

  This invention relates to certain novel imidazoline compounds and analogues thereof, to their use for the treatment of diabetes, diabetic complications, metabolic disorders, or related diseases where impaired glucose disposal is present, to pharmaceutical compositions comprising them, and to processes for their preparation.The compounds have the following formula: whereinX is -O-, -S-, or -NR5-;R5 is hydrogen, C1-8 alkyl, or an amino protecting group;R4 isY is -O-, -S-, or -NR8-;Y' is -O- or -S-;

  本发明涉及某些新型的咪唑啉化合物及其类似物，以及它们用于治疗糖尿病、糖尿病并发症、代谢紊乱或相关疾病中的糖利用受损情况，涉及包含它们的药物组合物，以及它们的制备过程。这些化合物的公式如下：其中X是-O-，-S-，或-NR5-；R5是氢，C1-8烷基，或氨基保护基团；R4是Y是-O-，-S-，或-NR8-；Y'是-O-或-S-；
• Cis-mono and disubstituted-2-methyl-3-[(piperazinyl) and
  申请人：American Cyanamid Company

  公开号：US04302589A1

  公开（公告）日：1981-11-24

  Novel substituted 3-[2-(4-phenyl or pyridyl-1-piperazinyl or piperidino)ethyl]indolines useful as antipsychotic agents in mammals as well as substituted 3-[2-(4-phenylpiperidino)ethyl]indole intermediates for their preparation.

  新型取代的3-[2-(4-苯基或吡啶基-1-哌嗪基或哌啶基)乙基]吲哚啉，作为哺乳动物中的抗精神病药物，以及用于其制备的取代的3-[2-(4-苯基哌啶基)乙基]吲哚中间体。
• Indole Inhibitors of Human Nonpancreatic Secretory Phospholipase A₂. 1. Indole-3-acetamides
  作者：Robert D. Dillard、Nicholas J. Bach、Susan E. Draheim、Dennis R. Berry、Donald G. Carlson、Nickolay Y. Chirgadze、David K. Clawson、Lawrence W. Hartley、Lea M. Johnson、Noel D. Jones、Emma R. McKinney、Edward D. Mihelich、Jennifer L. Olkowski、Richard W. Schevitz、Amy C. Smith、David W. Snyder、Cynthia D. Sommers、Jean-Pierre Wery

  DOI：10.1021/jm960485v

  日期：1996.1.1

  Phospholipases (PLAs) produce rate-limiting precursors in the biosynthesis of various types of biologically active lipids involved in inflammatory processes. Increased levels of human nonpancreatic secretory phospholipase A2 (hnps-PLA2) have been detected in several pathological conditions. An inhibitor of this enzyme could have therapeutic utility. A broad screening program was carried out to identify

  磷脂酶（PLA）在涉及炎症过程的各种类型生物活性脂质的生物合成中产生限速前体。在几种病理条件下已检测到人类非胰腺分泌型磷脂酶A2（hnps-PLA2）水平升高。该酶的抑制剂可以具有治疗用途。进行了广泛的筛选程序以鉴定可能抑制hnps-PLA2的化学结构。通过筛选程序生成的先导化合物之一是5-甲氧基-2-甲基-1-（苯甲基）-1H-吲哚-3-乙酸（13a）。我们描述了一系列吲哚-3-乙酰胺及其衍生化合物的合成，结构-活性关系以及药理活性。
• Indole compounds with <i>N</i>-ethyl morpholine moieties as CB2 receptor agonists for anti-inflammatory management of pain: synthesis and biological evaluation
  作者：Jiaojiao Li、Jing Ji、Ruibo Xu、Zhengfu Li

  DOI：10.1039/c9md00173e

  日期：——

  A series of indole compounds were designed and synthesized as CB2 agonist with high efficacy and selectivity.

  一系列吲哚化合物被设计和合成为高效选择性的CB2激动剂。
• N-benzyl-3-indoleacetic acids as antiinflammatory drugs
  申请人：Merck Frosst Canada, Inc.

  公开号：US05510368A1

  公开（公告）日：1996-04-23

  The invention encompasses the novel compound of Formula I as well as a method of treating inflammation and, in particular, cyclooxygenase-2 mediated diseases comprising administration to a patient in need of such treatment of a non-toxic therapeutically effective amount of a compound of Formula I. ##STR1## The invention also encompasses certain pharmaceutical compositions for treatment of inflammation and, in particular, cyclooxygenase-2 mediated diseases comprising compounds of Formula I.

  该发明涵盖了公式I的新化合物，以及一种用于治疗炎症，特别是环氧合酶-2介导的疾病的方法，包括向需要此类治疗的患者施用公式I化合物的非毒性治疗有效量。 该发明还涵盖了用于治疗炎症，特别是环氧合酶-2介导的疾病的某些药物组合，其中包括公式I的化合物。