ethyl (2Z)-3-amino-4-(3-methoxyphenyl)but-2-enoate | 1159576-81-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: ethyl (2Z)-3-amino-4-(3-methoxyphenyl)but-2-enoate
• 英文别名: ethyl (Z)-3-amino-4-(3-methoxyphenyl)but-2-enoate
• CAS: 1159576-81-4
• 化学式: C₁₃H₁₇NO₃
• 分子量: 235.283
• InChiKey: BYGDQKCOUKEWNH-LUAWRHEFSA-N

物化性质

• 沸点：
  390.5±42.0 °C(Predicted)
• 密度：
  1.105±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 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 (2Z)-3-amino-4-(3-methoxyphenyl)but-2-enoate 、 1,4-萘醌 在 zinc(II) iodide 作用下， 以 二氯甲烷 为溶剂， 以39%的产率得到ethyl 2-(3-methoxybenzyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
  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：

  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

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。
• Compounds and use thereof in the expansion of hematopoietic stem cells and/or hematopoietic progenitor cells
  申请人：UNIVERSITÉ DE MONTRÉAL

  公开号：US10647718B2

  公开（公告）日：2020-05-12

  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.

  本文提供并描述了通式化合物或其盐类或原药。这些化合物可用于扩大造血干细胞和/或造血祖细胞群。特别是，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、自身免疫性疾病和/或遗传性免疫缺陷疾病。
• COMPOUNDS AND USE THEREOF IN THE EXPANSION OF HEMATOPOIETIC STEM CELLS AND/OR HEMATOPOIETIC PROGENITOR CELLS
  申请人：Université de Montréal

  公开号：EP3134409B1

  公开（公告）日：2020-02-12
• Structural Optimization and Biological Evaluation of 2-Substituted 5-Hydroxyindole-3-carboxylates as Potent Inhibitors of Human 5-Lipoxygenase
  作者：Eva-Maria Karg、Susann Luderer、Carlo Pergola、Ulrike Bühring、Antonietta Rossi、Hinnak Northoff、Lidia Sautebin、Reinhard Troschütz、Oliver Werz

  DOI：10.1021/jm900212y

  日期：2009.6.11

  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.