(RS)-1-[3-(dodecylamino)phenyl]-1-hydroxy-1,2-dihydro-3H-pyrrolo[3,4-c]pyridin-3-one | 1346510-91-5

• 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: (RS)-1-[3-(dodecylamino)phenyl]-1-hydroxy-1,2-dihydro-3H-pyrrolo[3,4-c]pyridin-3-one
• 英文别名: 1-[3-(dodecylamino)phenyl]-1-hydroxy-2H-pyrrolo[3,4-c]pyridin-3-one
• CAS: 1346510-91-5
• 化学式: C₂₅H₃₅N₃O₂
• 分子量: 409.572
• InChiKey: VRAGRRVCHCWBDT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  30
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  74.2
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-碘十二烷 在 正丁基锂 、 potassium tert-butylate 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 38.0h， 生成 (RS)-1-[3-(dodecylamino)phenyl]-1-hydroxy-1,2-dihydro-3H-pyrrolo[3,4-c]pyridin-3-one
  参考文献：
  名称：

  Chemical synthesis, biological evaluation and structure–activity relationship analysis of azaisoindolinones, a novel class of direct enoyl-ACP reductase inhibitors as potential antimycobacterial agents

  摘要：

  The synthesis and biological evaluation of azaisoindolinone compounds embedding a lipophilic chain on the framework were performed. These compounds were designed as InhA inhibitors and as anti-Mycobacterium tuberculosis agents. Structure-activity relationships concerning the length and the location of the lipophilic chain around the azaisoindolinone framework, the suppression of the phenyl group, the bioisosteric substitution of ether link and alkylating of the tertiary hydroxyl and the hemiamidal nitrogen were also investigated, revealing insightful information and thereby enabling further diversification of the azaisoindolinone scaffold for new antitubercular agents. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.09.017

文献信息

• Chemical synthesis, biological evaluation and structure–activity relationship analysis of azaisoindolinones, a novel class of direct enoyl-ACP reductase inhibitors as potential antimycobacterial agents
  作者：Céline Deraeve、Ioana Miruna Dorobantu、Farah Rebbah、Frédéric Le Quéméner、Patricia Constant、Annaïk Quémard、Vania Bernardes-Génisson、Jean Bernadou、Geneviève Pratviel

  DOI：10.1016/j.bmc.2011.09.017

  日期：2011.11

  The synthesis and biological evaluation of azaisoindolinone compounds embedding a lipophilic chain on the framework were performed. These compounds were designed as InhA inhibitors and as anti-Mycobacterium tuberculosis agents. Structure-activity relationships concerning the length and the location of the lipophilic chain around the azaisoindolinone framework, the suppression of the phenyl group, the bioisosteric substitution of ether link and alkylating of the tertiary hydroxyl and the hemiamidal nitrogen were also investigated, revealing insightful information and thereby enabling further diversification of the azaisoindolinone scaffold for new antitubercular agents. (C) 2011 Elsevier Ltd. All rights reserved.