2-(4-nitrophenyl)-1H-pyrrolo[3,4-c]pyrydine-1,3(2H)-dione | 682758-91-4

• 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-(4-nitrophenyl)-1H-pyrrolo[3,4-c]pyrydine-1,3(2H)-dione
• 英文别名: LASSBio-1451；Pyrrolo[3,4-c]pyridine-1,3-dione, 2-(4-nitrophenyl)-；2-(4-nitrophenyl)pyrrolo[3,4-c]pyridine-1,3-dione
• CAS: 682758-91-4
• 化学式: C₁₃H₇N₃O₄
• mdl: MFCD03766735
• 分子量: 269.216
• InChiKey: PJINHSALNIXCTG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  96.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-[(4-Nitrophenyl)carbamoyl]pyridine-3-carboxylic acid 在 sodium acetate 、 乙酸酐 作用下， 反应 1.0h， 以37%的产率得到2-(4-nitrophenyl)-1H-pyrrolo[3,4-c]pyrydine-1,3(2H)-dione
  参考文献：
  名称：

  Microwave-assisted synthesis and structure–activity relationships of neuroactive pyrazolo[3,4-b]pyrrolo[3,4-d]pyridine derivatives

  摘要：

  We described herein the optimization of the synthetic methodology exploited to obtain the pyrazolo[3,4-b]pyrrolo[3,4-d]pyridine sedative prototype 1a and novel analogues designed by successive molecular simplifications. By applying microwave irradiation during the hetero Diels-Alder key-step to obtain the heterotricyclic scaffold, under solvent-free conditions, we were able to obtain the desired compounds in drastically shorter times and better yields. Additionally, in vivo evaluation of the sedative effects of these heterocyclic derivatives showed that 1a and the novel structurally-related analogue 1e were the most efficient compounds to impair the locomotor activity in mice at the dose of 10 mu mol/kg. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.11.038

文献信息

• Microwave-assisted synthesis and structure–activity relationships of neuroactive pyrazolo[3,4-b]pyrrolo[3,4-d]pyridine derivatives
  作者：Nailton M. Nascimento-Júnior、Thaiana C.F. Mendes、Daniella M. Leal、Claudia Maria N. Corrêa、Roberto T. Sudo、Gisele Zapata-Sudo、Eliezer J. Barreiro、Carlos A.M. Fraga

  DOI：10.1016/j.bmcl.2009.11.038

  日期：2010.1

  We described herein the optimization of the synthetic methodology exploited to obtain the pyrazolo[3,4-b]pyrrolo[3,4-d]pyridine sedative prototype 1a and novel analogues designed by successive molecular simplifications. By applying microwave irradiation during the hetero Diels-Alder key-step to obtain the heterotricyclic scaffold, under solvent-free conditions, we were able to obtain the desired compounds in drastically shorter times and better yields. Additionally, in vivo evaluation of the sedative effects of these heterocyclic derivatives showed that 1a and the novel structurally-related analogue 1e were the most efficient compounds to impair the locomotor activity in mice at the dose of 10 mu mol/kg. (C) 2009 Elsevier Ltd. All rights reserved.