2-(3-pyridyl)-6,7-dihydro-[5H]-pyrrolo[1,2-a]imidazole | 408498-43-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2-(3-pyridyl)-6,7-dihydro-[5H]-pyrrolo[1,2-a]imidazole
• 英文别名: 2-(Pyridin-3-yl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazole；2-pyridin-3-yl-6,7-dihydro-5H-pyrrolo[1,2-a]imidazole
• CAS: 408498-43-1
• 化学式: C₁₁H₁₁N₃
• 分子量: 185.228
• InChiKey: BASXAKGFCMKLMU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  30.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(3-pyridyl)-6,7-dihydro-[5H]-pyrrolo[1,2-a]imidazole 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 二氯甲烷 为溶剂， 生成 3-bromo-2-(3-pyridyl)-6,7-dihydro-[5H]-pyrrolo[1,2-a]imidazole
  参考文献：
  名称：

  Open Source Antibiotics: Simple Diarylimidazoles Are Potent against Methicillin-Resistant Staphylococcus aureus

  摘要：

  DOI：

  10.1021/acsinfecdis.3c00286
• 作为产物：
  描述：

  3-乙酰基吡啶 在 氢溴酸 、 溴 、 sodium carbonate 作用下， 以 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成 2-(3-pyridyl)-6,7-dihydro-[5H]-pyrrolo[1,2-a]imidazole
  参考文献：
  名称：

  Identification of Novel Inhibitors of the Transforming Growth Factor β1 (TGF-β1) Type 1 Receptor (ALK5)

  摘要：

  Screening of our internal compound collection for inhibitors of the transforming growth factor beta1 (TGF-beta1) type I receptor (ALK5) identified several hits. Optimization of the dihydropyrroloimidazole hit 2 by introduction of a 2-pyridine and 3,4-methylenedioxyphenyl group gave 7, a selective ALK5 inhibitor. With this information, optimization of the triarylimidazole hit 8 gave the selective inhibitor 14, which inhibits TGF-beta1-induced fibronectin mRNA formation while displaying no measurable cytotoxicity in the 48 h XTT assay.

  DOI：

  10.1021/jm010493y

文献信息

• Identification of Novel Inhibitors of the Transforming Growth Factor β1 (TGF-β1) Type 1 Receptor (ALK5)
  作者：James F. Callahan、Joelle L. Burgess、James A. Fornwald、Laramie M. Gaster、John D. Harling、Frank P. Harrington、Jag Heer、Chet Kwon、Ruth Lehr、A. Mathur、Barbara A. Olson、Joseph Weinstock、Nicholas J. Laping

  DOI：10.1021/jm010493y

  日期：2002.2.1

  Screening of our internal compound collection for inhibitors of the transforming growth factor beta1 (TGF-beta1) type I receptor (ALK5) identified several hits. Optimization of the dihydropyrroloimidazole hit 2 by introduction of a 2-pyridine and 3,4-methylenedioxyphenyl group gave 7, a selective ALK5 inhibitor. With this information, optimization of the triarylimidazole hit 8 gave the selective inhibitor 14, which inhibits TGF-beta1-induced fibronectin mRNA formation while displaying no measurable cytotoxicity in the 48 h XTT assay.
• Open Source Antibiotics: Simple Diarylimidazoles Are Potent against Methicillin-Resistant <i>Staphylococcus aureus</i>
  作者：Dana M. Klug、Edwin G. Tse、Daniel G. Silva、Yafeng Cao、Susan A. Charman、Jyoti Chauhan、Elly Crighton、Maria Dichiara、Chris Drake、David Drewry、Flavio da Silva Emery、Lori Ferrins、Lee Graves、Emily Hopkins、Thomas A. C. Kresina、Álvaro Lorente-Macías、Benjamin Perry、Richard Phipps、Bruno Quiroga、Antonio Quotadamo、Giada N. Sabatino、Anthony Sama、Andreas Schätzlein、Quillon J. Simpson、Jonathan Steele、Julia Shanu-Wilson、Peter Sjö、Paul Stapleton、Christopher J. Swain、Alexandra Vaideanu、Huanxu Xie、William Zuercher、Matthew H. Todd

  DOI：10.1021/acsinfecdis.3c00286

  日期：2023.12.8