ethyl 3-(dimethylamino)-2-(5-methyl-3-nitropyridin-2-yl)acrylate | 533910-51-9

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: ethyl 3-(dimethylamino)-2-(5-methyl-3-nitropyridin-2-yl)acrylate
• 英文别名: 3-Dimethylamino-2-(5-methyl-3-nitro-pyridin-2-yl)-acrylic acid ethyl ester；ethyl 3-(dimethylamino)-2-(5-methyl-3-nitropyridin-2-yl)prop-2-enoate
• CAS: 533910-51-9
• 化学式: C₁₃H₁₇N₃O₄
• 分子量: 279.296
• InChiKey: MGIZJWIJVKXBDL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.76
• 重原子数：
  20.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  85.57
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  ethyl 3-(dimethylamino)-2-(5-methyl-3-nitropyridin-2-yl)acrylate 在 铁粉 、 potassium carbonate 、 溶剂黄146 、 1-丙基磷酸酐 、 三乙胺 、 lithium hydroxide 作用下， 以 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.08h， 生成 N-(2-hydroxyethyl)-1-((6-methoxy-5-methylpyrimidin-4-yl)-methyl)-6-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide
  参考文献：
  名称：

  Azaindoles: Noncovalent DprE1 Inhibitors from Scaffold Morphing Efforts, Kill Mycobacterium tuberculosis and Are Efficacious in Vivo

  摘要：

  We report 1,4-azaindoles as a new inhibitor class that kills Mycobacterium tuberculosis in vitro and demonstrates efficacy in mouse tuberculosis models. The series emerged from scaffold morphing efforts and was demonstrated to noncovalently inhibit decaprenylphosphoryl-beta-D-ribose2'-epimerase (DprE1). With "drug-like" properties and no expectation of pre-existing resistance in the clinic, this chemical class has the potential to be developed as a therapy for drug-sensitive and drug-resistant tuberculosis.

  DOI：

  10.1021/jm401382v
• 作为产物：
  描述：

  1-(tert-butyl) 3-ethyl 2-(5-methyl-3-nitropyridin-2-yl)malonate 在 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 26.0h， 生成 ethyl 3-(dimethylamino)-2-(5-methyl-3-nitropyridin-2-yl)acrylate
  参考文献：
  名称：

  [EN] CONDENSED AZAHETEROARYL COMPOUNDS HAVING ANTIBACTERIAL ACTIVITY AGAINST TUBERCULOSIS BACTERIA
  [FR] COMPOSÉS AZAHÉTÉROARYLES CONDENSÉS AYANT UNE ACTIVITÉ ANTIBACTÉRIENNE CONTRE LES BACTÉRIES DE LA TUBERCULOSE

  摘要：

  本发明涉及一般式（I）的新化合物，它们的对映体、非对映体、药学上可接受的盐或其前药，适用于治疗细菌感染。一般式（I）的化合物表现出DprE1酶抑制活性。

  公开号：

  WO2019239382A1

文献信息

• 1H-pyrrolo [3,2-b] pyridine-3-carboxylic acid amines as GABAA receptor ligands
  申请人：Neurogen Corporation

  公开号：US06673811B1

  公开（公告）日：2004-01-06

  Disclosed are 1H-Pyrrolo[3,2-b]pyridine-3-carboxylic acid amides that bind to the benzodiazepine site of GABAA receptors. Such compounds can be used to modulate ligand binding to GABAA receptors in vivo and in vitro, and are particularly useful in the treatment of a variety of central nervous system (CNS) disorders in humans, domesticated companion animals, and livestock animals.

  本发明涉及1H-吡咯并[3,2-b]吡啶-3-羧酸酰胺，其结合到GABAA受体的苯二氮平位点。这种化合物可以用于体内和体外调节GABAA受体的配体结合，并且在人类、家畜宠物和牲畜的多种中枢神经系统（CNS）疾病治疗中特别有用。
• Lead Optimization of 1,4-Azaindoles as Antimycobacterial Agents
  作者：Pravin S. Shirude、Radha K. Shandil、M. R. Manjunatha、Claire Sadler、Manoranjan Panda、Vijender Panduga、Jitendar Reddy、Ramanatha Saralaya、Robert Nanduri、Anisha Ambady、Sudha Ravishankar、Vasan K. Sambandamurthy、Vaishali Humnabadkar、Lalit K. Jena、Rudrapatna S. Suresh、Abhishek Srivastava、K. R. Prabhakar、James Whiteaker、Robert E. McLaughlin、Sreevalli Sharma、Christopher B. Cooper、Khisi Mdluli、Scott Butler、Pravin S. Iyer、Shridhar Narayanan、Monalisa Chatterji

  DOI：10.1021/jm500571f

  日期：2014.7.10

  In a previous report, we described the discovery of 1,4-azaindoles, a chemical series with excellent in vitro and in vivo antimycobacterial potency through noncovalent inhibition of decaprenylphosphoryl-beta-D-ribose-2'-epimerase (DprE1). Nevertheless, high mouse metabolic turnover and phosphodiesterase 6 (PDE6) off-target activity limited its advancement. Herein, we report lead optimization of this series, culminating in potent, metabolically stable compounds that have a robust pharmacokinetic profile without any PDE6 liability. Furthermore, we demonstrate efficacy for 1,4-azaindoles in a rat chronic TB infection model. We believe that compounds from the 1,4-azaindole series are suitable for in vivo combination and safety studies.
• 1H-PYRROLO(3,2-B)PYRIDINE-3-CARBOXYLIC ACID AMIDES
  申请人：Neurogen Corporation

  公开号：EP1453831A1

  公开（公告）日：2004-09-08
• CONDENSED AZAHETEROARYL COMPOUNDS HAVING ANTIBACTERIAL ACTIVITY AGAINST TUBERCULOSIS BACTERIA
  申请人：CADILA HEALTHCARE LIMITED

  公开号：US20210292333A1

  公开（公告）日：2021-09-23

  Present invention relates to novel compound of general formula (I), their enantiomers, their diastereomers, their pharmaceutically accepted salts, or pro-drugs thereof, which are useful for the treatment of bacterial infection. The compounds of general formula (I) exhibit DprE1 enzyme inhibitory activity.
• US6673811B1
  申请人：——

  公开号：US6673811B1

  公开（公告）日：2004-01-06