2-benzyl-2H-pyrrolo[3,4-c]pyridine-6-carboxylic acid ethyl ester | 927203-49-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并吡啶类
• 英文名称: 2-benzyl-2H-pyrrolo[3,4-c]pyridine-6-carboxylic acid ethyl ester
• 英文别名: 2-benzyl-2H-pyrrolo[3,4-c]pyridine-6-ethylcarboxylate；2-Benzyl-2H-pyrrolo[3,4-c]pyridine-6-carboxylic acid ethyl ester；ethyl 2-benzylpyrrolo[3,4-c]pyridine-6-carboxylate
• CAS: 927203-49-4
• 化学式: C₁₇H₁₆N₂O₂
• 分子量: 280.326
• InChiKey: LWPUQIZKKUMWPH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-benzyl-2H-pyrrolo[3,4-c]pyridine-6-carboxylic acid ethyl ester 在 N-溴代丁二酰亚胺(NBS) 、 水 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 30.0h， 生成
  参考文献：
  名称：

  Transnitrosation of Thiols from Aliphatic N-Nitrosamines:  S-Nitrosation and Indirect Generation of Nitric Oxide

  摘要：

  S-Nitrosothiols and heme nitrosyl species are nitric oxide (NO)-derived metabolites that provide an endogenous reservoir of NO and also play roles in protein S-nitrosation, that is, transnitrosation of thiols (or thiolates) in proteins, thereby regulating protein functions and signal transduction pathways. Intriguingly, endogenous N-nitrosamines are present in similar abundance to S-nitrosothiols, and though they are thought to play similar physiological roles to S-nitrosothiols, their transnitrosation reactivities and their contribution to biological events are little understood. Herein we report aliphatic N-nitroso derivatives of 7-azabicyclo[2.2.1]heptanes, which do not act as NO donors themselves, but can transnitrosate thiols. On the basis of the calculated activation energies of transnitrosation and the aorta smooth-muscle relaxation activities of these N-nitrosamines, we present a possible scenario of Stransnitrosation from aliphatic N-nitrosamines, leading to indirect generation of NO.

  DOI：

  10.1021/ja0658259
• 作为产物：
  描述：

  1-benzyl-1H-pyrrole-3,4-dicarbonitrile 在 二异丁基氢化铝 、 二乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 2-benzyl-2H-pyrrolo[3,4-c]pyridine-6-carboxylic acid ethyl ester
  参考文献：
  名称：

  Transnitrosation of Thiols from Aliphatic N-Nitrosamines:  S-Nitrosation and Indirect Generation of Nitric Oxide

  摘要：

  S-Nitrosothiols and heme nitrosyl species are nitric oxide (NO)-derived metabolites that provide an endogenous reservoir of NO and also play roles in protein S-nitrosation, that is, transnitrosation of thiols (or thiolates) in proteins, thereby regulating protein functions and signal transduction pathways. Intriguingly, endogenous N-nitrosamines are present in similar abundance to S-nitrosothiols, and though they are thought to play similar physiological roles to S-nitrosothiols, their transnitrosation reactivities and their contribution to biological events are little understood. Herein we report aliphatic N-nitroso derivatives of 7-azabicyclo[2.2.1]heptanes, which do not act as NO donors themselves, but can transnitrosate thiols. On the basis of the calculated activation energies of transnitrosation and the aorta smooth-muscle relaxation activities of these N-nitrosamines, we present a possible scenario of Stransnitrosation from aliphatic N-nitrosamines, leading to indirect generation of NO.

  DOI：

  10.1021/ja0658259

文献信息

• Transnitrosation of Thiols from Aliphatic <i>N</i>-Nitrosamines:  <i>S</i>-Nitrosation and Indirect Generation of Nitric Oxide
  作者：Takahiro Yanagimoto、Takeshi Toyota、Norio Matsuki、Yumi Makino、Seiichi Uchiyama、Tomohiko Ohwada

  DOI：10.1021/ja0658259

  日期：2007.1.1

  S-Nitrosothiols and heme nitrosyl species are nitric oxide (NO)-derived metabolites that provide an endogenous reservoir of NO and also play roles in protein S-nitrosation, that is, transnitrosation of thiols (or thiolates) in proteins, thereby regulating protein functions and signal transduction pathways. Intriguingly, endogenous N-nitrosamines are present in similar abundance to S-nitrosothiols, and though they are thought to play similar physiological roles to S-nitrosothiols, their transnitrosation reactivities and their contribution to biological events are little understood. Herein we report aliphatic N-nitroso derivatives of 7-azabicyclo[2.2.1]heptanes, which do not act as NO donors themselves, but can transnitrosate thiols. On the basis of the calculated activation energies of transnitrosation and the aorta smooth-muscle relaxation activities of these N-nitrosamines, we present a possible scenario of Stransnitrosation from aliphatic N-nitrosamines, leading to indirect generation of NO.