(RS)-1-hydroxy-1-[3-(octyloxy)phenyl]-1,2-dihydro-3H-pyrrolo[3,4-c]pyridin-3-one | 1181581-52-1

• 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-hydroxy-1-[3-(octyloxy)phenyl]-1,2-dihydro-3H-pyrrolo[3,4-c]pyridin-3-one
• 英文别名: 1-(3-octyloxyphenyl)-1-hydroxy-1,2-dihydro-3H-pyrrolo[3,4-c]pyridin-3-one；1-hydroxy-1-(3-octoxyphenyl)-2H-pyrrolo[3,4-c]pyridin-3-one
• CAS: 1181581-52-1
• 化学式: C₂₁H₂₆N₂O₃
• 分子量: 354.449
• InChiKey: NAOWIHVYFYKGSP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  71.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  间溴苯酚 在 正丁基锂 、 potassium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 13.0h， 生成 (RS)-1-hydroxy-1-[3-(octyloxy)phenyl]-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

• NOVEL ANTI-INFECTIOUS DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF, PHARMACEUTICAL COMPOSITIONS CONTAINING SAME AND USES OF SAID DERIVATIVES IN TREATMENT
  申请人：Bernadou Jean

  公开号：US20110092536A1

  公开（公告）日：2011-04-21

  The invention relates to bi-substrate inhibitor molecules associating (i) a pyridine, pyridinium or dihydropyridine-type structure allied to active metabolites of isoniazide, or related structures, and (ii) a hydrophobic substituent. The invention also relates to the method for producing said molecules, to the pharmaceutical compositions containing said molecules, and to the use thereof as inhibitors of enoyl reductase for the preparation of a medicament, especially an anti-infectious medicament for the treatment of tuberculosis.

  该发明涉及与异烟肼的活性代谢产物相关的吡啶、吡啶盐或二氢吡啶类型结构以及疏水取代基相结合的双底物抑制分子。该发明还涉及制备该分子的方法、含有该分子的药物组合物，以及将其用作烯醇还原酶抑制剂的用途，用于制备药物，特别是用于治疗结核病的抗感染药物。
• NOUVEAUX DÉRIVÉS ANTI-INFECTIEUX, LEUR PROCÉDÉ DE PRÉPARATION, COMPOSITIONS PHARMACEUTIQUES LES CONTENANT ET LEURS UTILISATIONS EN THÉRAPEUTIQUE
  申请人：Centre National de la Recherche Scientifique (CNRS)

  公开号：EP2240449B1

  公开（公告）日：2016-01-06
• US8710073B2
  申请人：——

  公开号：US8710073B2

  公开（公告）日：2014-04-29
• [EN] NOVEL ANTI-INFECTIOUS DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF, PHARMACEUTICAL COMPOSITIONS CONTAINING SAME AND USES OF SAID DERIVATIVES IN TREATMENT<br/>[FR] NOUVEAUX DÉRIVÉS ANTI-INFECTIEUX, LEUR PROCÉDÉ DE PRÉPARATION, COMPOSITIONS PHARMACEUTIQUES LES CONTENANT ET LEURS UTILISATIONS EN THÉRAPEUTIQUE
  申请人：CENTRE NAT RECH SCIENT

  公开号：WO2009101345A1

  公开（公告）日：2009-08-20

  La présente invention est relative à des molécules d'inhibiteurs bi-substrats associant (i) une structure apparentée aux métabolites actifs de l'isoniazide et de type pyridine, pyridinium ou dihydropyridine ou structures apparentées et (ii) un substituant hydrophobe, à leur procédé de préparation, aux compositions pharmaceutiques les contenant et à leur utilisation à titre d'inhibiteur d'énoylréductase pour la préparation d'un médicament, notamment d'un médicament anti-infectieux pour le traitement de la tuberculose.
• 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.