2-(3-吡咯基)乙酸乙酯 | 71616-57-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 中文名称: 2-(3-吡咯基)乙酸乙酯
• 英文名称: ethyl pyrrole-3-acetate
• 英文别名: Ethyl 2-(3-pyrrolyl)acetate；ethyl 2-(1H-pyrrol-3-yl)acetate
• CAS: 71616-57-4
• 化学式: C₈H₁₁NO₂
• 分子量: 153.181
• InChiKey: OPLGNZRWCMKEDJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  42.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(3-吡咯基)乙酸乙酯 在 potassium phosphate 、 copper(l) iodide 、 (1S,2S)-(+)-1,2-环己二胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 48.0h， 生成 ethyl 2-[1-(6-indol-1-ylpyrazin-2-yl)pyrrol-3-yl]acetate
  参考文献：
  名称：

  Discovery and structure–activity relationship of 2,6-disubstituted pyrazines, potent and selective inhibitors of protein kinase CK2

  摘要：

  We report the discovery and structure-activity relationship of 2,6-disubstituted pyrazines, which are potent and selective CK2 inhibitors. Lead compound 1 was identified, and derivatives were prepared to develop potent inhibitory activity. As a result, we obtained compound 7, which was the smallest unit that retained potency. Then, introducing an aminoalkyl group at the 6-position of the indazole ring resulted in improved efficacy in both enzymatic and cell-based CK2 inhibition assays. Moreover, compound 13 showed selectivity against other kinases and in vivo efficacy in a rat nephritis model. These results show that 2,6-disubstituted pyrazines have potential as therapeutic agents for nephritis. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.05.006
• 作为产物：
  描述：

  2-氧代-2-(1H-吡咯-3-基)乙酸乙酯 在 palladium 10% on activated carbon 作用下， 以 1,4-二氧六环 、 水 为溶剂， 生成 2-(3-吡咯基)乙酸乙酯
  参考文献：
  名称：

  3-Aryl-4-pyrrolyl-maleimides 作为糖原合酶激酶-3β 抑制剂的设计、合成和评价

  摘要：

  设计、合成了一系列 3-芳基-4-吡咯基-马来酰亚胺，并评估了它们的糖原合酶激酶-3β（GSK-3β）抑制活性。大多数化合物对 GSK-3β 表现出有效的活性。其中，化合物 11a、11c、11h、11i 和 11j 显着降低了 Aβ 诱导的 Tau 过度磷酸化，表明在细胞水平上抑制了 GSK-3β。基于获得的实验数据讨论了构效关系。

  DOI：

  10.1002/ardp.201300008

文献信息

• Structure-Activity Relationships of Pyrazine-Based CK2 Inhibitors: Synthesis and Evaluation of 2,6-Disubstituted Pyrazines and 4,6-Disubstituted Pyrimidines
  作者：Yamato Suzuki、Jérôme Cluzeau、Takafumi Hara、Akira Hirasawa、Gozoh Tsujimoto、Shinya Oishi、Hiroaki Ohno、Nobutaka Fujii

  DOI：10.1002/ardp.200700269

  日期：2008.9

  Structually related to the known CK2 inhibitors, 2,6‐disubstituted pyrazine and 4,6‐disubstituted pyrimidine derivatives were synthesized and their inhibitory activities toward CK2α and CK2α′ were evaluated. Structure‐activity relationship study has revealed that several pyrazine derivatives bearing a (pyrrol‐3‐yl)acetic acid and a monosubstituted aniline possess potent inhibitory activities.

  与已知的 CK2 抑制剂结构相关，合成了 2,6-二取代吡嗪和 4,6-二取代嘧啶衍生物，并评估了它们对 CK2α 和 CK2α' 的抑制活性。构效关系研究表明，几种带有（吡咯-3-基）乙酸和单取代苯胺的吡嗪衍生物具有有效的抑制活性。
• Isomeric Benzoylpyrroleacetic Acids: Some Structural Aspects for Aldose Reductase Inhibitory and Anti-Inflammatory Activities
  作者：Vassilis J. Demopoulos、Eleni Rekka

  DOI：10.1002/jps.2600840119

  日期：1995.1

  A number of isomeric benzoylpyrroleacetic acids (1-6) were prepared and tested in vitro for rat lenses aldose reductase activity. These pyrrole derivatives are structurally related to the acidic nonsteroidal anti-inflammatory drugs. Therefore, their anti-inflammatory properties were also evaluated in the carrageenan-induced rat paw edema model. Inhibition of the aldose reductase enzyme was found to

  制备了许多异构的苯甲酰基吡咯烷乙酸（1-6），并在体外测试了大鼠晶状体醛糖还原酶的活性。这些吡咯衍生物在结构上与酸性非甾体抗炎药有关。因此，还在角叉菜胶诱导的大鼠爪水肿模型中评估了它们的抗炎特性。发现醛糖还原酶的抑制取决于苯甲酰基和乙酸官能团的存在。当这些部分被引入吡咯环的位置1和3时，导致更好的活性。然而，对于抗炎活性，乙酸基不是必需的，并且在某些情况下，乙酸基的存在导致活性丧失。3-苄基吡咯-1-乙酸（6）的IC50为2。在醛糖还原酶测定中为5 microM，与alrestatin（1.5 microM）相当。然而，在大鼠爪模型中，化合物6在最高100 mg / kg ip的剂量下未显示出抗炎活性。
• NITROGENOUS MACROCYCLIC COMPOUND, PREPARATION METHOD THEREFOR, PHARMACEUTICAL COMPOSITION AND APPLICATION THEREOF
  申请人：Luoxin Pharmaceutical (Shanghai) Co., Ltd.

  公开号：EP3539960A1

  公开（公告）日：2019-09-18

  Disclosed in the present invention are a nitrogenous macrocyclic compound, a preparation method therefor, a pharmaceutical composition and an application thereof. The present invention provides a nitrogenous macrocyclic compound represented by formula III-0, a tautomer thereof, an optical isomer thereof, a hydrate thereof, a solvate thereof, a pharmacologically acceptable salt thereof, or a prodrug thereof. The compound can be effectively bond with bromodomains of a BET family: BRD4, BRD3, BRD2, and BRDT, so as to adjust transcription of a downstream gene c-myc and a related target gene thereof, and futher to adjust a downstream signal path and play a particular role, comprising treating diseases such as inflammatory diseases, cancers, and AIDS.

  本发明公开了一种含氮大环化合物、其制备方法、药物组合物及其应用。本发明提供了一种由式 III-0 表示的含氮大环化合物、其同分异构体、其光学异构体、其水合物、其溶液、其药理学上可接受的盐或其原药。该化合物可与 BET 家族的溴结构域有效结合：BRD4、BRD3、BRD2 和 BRDT，从而调节下游基因 c-myc 及其相关靶基因的转录，进而调节下游信号通路，发挥特殊作用，包括治疗炎症性疾病、癌症和艾滋病等疾病。
• [EN] NITROGENOUS MACROCYCLIC COMPOUND, PREPARATION METHOD THEREFOR, PHARMACEUTICAL COMPOSITION AND APPLICATION THEREOF<br/>[FR] COMPOSÉ MACROCYCLIQUE AZOTÉ, SON PROCÉDÉ DE PRÉPARATION, SA COMPOSITION PHARMACEUTIQUE ET SON APPLICATION<br/>[ZH] 一种含氮大环类化合物、其制备方法、药物组合物及应用
  申请人：SHANDONG LUOXIN PHARMACY STOCK

  公开号：WO2018086605A1

  公开（公告）日：2018-05-17

  本发明公开了一种含氮大环类化合物、其制备方法、药物组合物及应用。本发明提供了一种如式III-0所示的含氮大环类化合物、其互变异构体、其光学异构体、其水合物、其溶剂化物、其药学上可接受的盐或其前药。该化合物可有效地结合BET家族BRD4、BRD3、BRD2和BRDT的溴结构域，以调控下游基因c-myc和其相关靶基因的转录，进而调节下游的信号通路，发挥特定作用，包括治疗疾病如炎性疾病、癌症和AIDS。
• Demopoulos, Vassilis J., Synthetic Communications, 1989, vol. 19, # 13-14, p. 2585 - 2594
  作者：Demopoulos, Vassilis J.

  DOI：——

  日期：——