1H-吡咯并[3,2-b]吡啶-3-羧酸乙酯 | 178896-76-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并吡啶类
• 中文名称: 1H-吡咯并[3,2-b]吡啶-3-羧酸乙酯
• 英文名称: ethyl pyrrolo[3,2-b]pyridine-3-carboxylate
• 英文别名: Ethyl 1H-pyrrolo[3,2-B]pyridine-3-carboxylate
• CAS: 178896-76-9
• 化学式: C₁₀H₁₀N₂O₂
• mdl: MFCD15144589
• 分子量: 190.202
• InChiKey: SSOULCZNJMHBOC-UHFFFAOYSA-N

物化性质

• 沸点：
  355.9±22.0 °C(Predicted)
• 密度：
  1.272±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  55
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1H-吡咯并[3,2-b]吡啶-3-羧酸乙酯 在 potassium carbonate 、 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 8.0h， 生成 N-(cyclopropylmethyl)-1-(4-methylbenzyl)-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：

  ethyl 3-(dimethylamino)-2-(3-nitropyrid-2-yl)propenoate 在 铁粉 、 溶剂黄146 作用下， 反应 2.0h， 生成 1H-吡咯并[3,2-b]吡啶-3-羧酸乙酯
  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

文献信息

• ACYCLIC COMPOUNDS HAVING 5-HT6 RECEPTOR AFFINITY
  申请人：Conticello Richard

  公开号：US20100029629A1

  公开（公告）日：2010-02-04

  The present disclosure provides compounds having affinity for the 5-HT 6 receptor which are of the formula (I): wherein R 1 , R 2 , R 5 , Q, G, Ar, m, and n are as defined herein. The disclosure also relates to methods of preparing such compounds, compositions containing such compounds, and methods of use thereof.

  本公开提供了具有对5-HT 6 受体亲和力的化合物，其化学式为（I）： 其中R1、R2、R5、Q、G、Ar、m和n如本文所定义。本公开还涉及制备这种化合物的方法、含有这种化合物的组合物以及使用这些化合物的方法。
• [EN] SELECTIVE INHIBITORS OF CLINICALLY IMPORTANT MUTANTS OF THE EGFR TYROSINE KINASE<br/>[FR] INHIBITEURS SÉLECTIFS DE MUTANTS CLINIQUEMENT IMPORTANTS DE LA TYROSINE KINASE DE L'EGFR
  申请人：CS PHARMASCIENCES INC

  公开号：WO2017120429A1

  公开（公告）日：2017-07-13

  The present invention provides compounds of Formula (I) or a subgeneric structure or species thereof, or a pharmaceutically acceptable salt, ester, solvate, and/or prodrug thereof, and methods and compositions for treating or ameliorating abnormal cell proliferative disorders, such as cancer, wherein A, R2, R3, R10, E1, E2, E3, Y, and Z are as defined herein.

  本发明提供了式（I）的化合物或其亚类结构或种属，或其药学上可接受的盐、酯、溶剂化合物和/或前药，以及用于治疗或改善异常细胞增殖性疾病，如癌症的方法和组合物，其中A、R2、R3、R10、E1、E2、E3、Y和Z如本文所定义。
• DIMERIC IAP INHIBITORS
  申请人：Chen Zhuoliang

  公开号：US20130309247A1

  公开（公告）日：2013-11-21

  The present invention provides compounds of formula M-L-M′ (where M and M′ are each independently a monomeric moiety of Formula (I) and L is a linker). The dimeric compounds have been found to be effective in promoting apoptosis in rapidly dividing cells. (I)

  本发明提供了公式M-L-M'的化合物（其中M和M'分别独立地是公式（I）的单体基团，L是连接剂）。已发现二聚化合物在促进快速分裂细胞的凋亡方面具有有效性。 (I)
• Selective inhibitors of clinically important mutants of the EGFR tyrosine kinase
  申请人：CS PHARMATECH LIMITED

  公开号：US10435388B2

  公开（公告）日：2019-10-08

  The present invention provides compounds of Formula (I) or a subgeneric structure or species thereof or a pharmaceutically acceptable salt, ester, solvate, and/or prodrug thereof and methods and compositions for treating or ameliorating abnormal cell proliferative disorders, such as cancer, wherein A, R2, R3, R10, E1, E2, E3, Y, and Z are as defined herein.

  本发明提供了式(I)化合物或其亚属结构或种类或其药学上可接受的盐、酯、溶液剂和/或原药，以及用于治疗或改善异常细胞增殖性疾病（如癌症）的方法和组合物，其中A、R2、R3、R10、E1、E2、E3、Y和Z如本文所定义。
• 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.