5-氯-1H-咪唑[4,5-b]吡啶-2(3H)-酮 | 40851-98-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并吡啶类
• 中文名称: 5-氯-1H-咪唑[4,5-b]吡啶-2(3H)-酮
• 中文别名: 5-氯-1,3-二氢-2H-咪唑并[4,5-b]吡啶-2-酮；5-氯-1H-咪唑[4,5-B]吡啶-2(3H)-酮；5-氯-1.3-二氢-2H-咪唑并[4.5-b]吡啶-2-酮
• 英文名称: 5-chloroimidazo<4,5-b>pyridin-2-one
• 英文别名: 5-chloro-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one；5-chloro-1,3-dihydro-imidazo[4,5-b]pyridin-2-one；5-Chloro-1H-imidazo[4,5-b]pyridin-2(3H)-one；5-chloro-1,3-dihydroimidazo[4,5-b]pyridin-2-one
• CAS: 40851-98-7
• 化学式: C₆H₄ClN₃O
• mdl: MFCD06659688
• 分子量: 169.57
• InChiKey: XJFIKRXIJXAJGH-UHFFFAOYSA-N

物化性质

• 密度：
  1.82

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  5-氯-1H-咪唑[4,5-b]吡啶-2(3H)-酮 、 碘甲烷 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 以27.8%的产率得到1,3-dimethyl-5-chloroimidazo<4,5-b>pyridin-2-one
  参考文献：
  名称：

  Bianchi; Butti; Rossi, European Journal of Medicinal Chemistry, 1983, vol. 18, # 6, p. 501 - 506

  摘要：

  DOI：
• 作为产物：
  描述：

  6-氯-2,3-二氨基吡啶 、 三光气 在 sodium hydroxide 、 盐酸 作用下， 以 二氯甲烷 、 水 为溶剂， 以47%的产率得到5-氯-1H-咪唑[4,5-b]吡啶-2(3H)-酮
  参考文献：
  名称：

  Synthesis and biological activity of splitomicin analogs targeted at human NAD+-dependent histone deacetylases (sirtuins)

  摘要：

  Small molecules interfering with posttranslational modification of histones are of interest as tools to study epigenetic regulation of gene transcription. Specifically, drugs that interfere with histone deacetylation could be useful to induce differentiation, growth arrest as well as apoptotic cell death in tumor cells. One class of histone deacetylases is known as sirtuins some of which (Saccharomyces cerevisiae Sir2) are for example inhibited by the lactone splitomicin leading to telomeric silencing in yeast. However, splitomicin is only a micromolar inhibitor of yeast Sir2 and does not inhibit human subtypes and the lactone is prone to hydrolytic ring opening. In preliminary SAR-studies, splitomicin analogs lacking this hydrolytically labile ring were described as inactive while the naphthalene moiety could successfully be replaced by smaller aromatic rings in a fragment-like dihydrocoumarin. Here we report the synthesis and biological activity of a series of hydrolytically stable analogs with activity against human SIRT1 and 2. These comparatively small compounds characterized by high ligand efficiency are used as a starting point toward the development of specific inhibitors of histone deacetylases from the class of sirtuins. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.01.026

文献信息

• Spiro[isobenzofuran-1,4'-piperidin]-3-ones and 3H-spiroisobenzofuran-1,4'-piperidines
  申请人：NEUROGEN CORPORATION

  公开号：US20030036652A1

  公开（公告）日：2003-02-20

  Substituted spiro[isobenzofuran-1,4′-piperidin]-3-ones and 3H-spiroisobenzofuran-1,4′-piperidines capable of modulating NPY5 receptor activity are provided. Such compounds may be used to modulate ligand binding to NPY5 receptors in vivo or in vitro, and are particularly useful in the treatment of a variety of disorders (e.g., eating disorders such as obesity or bulimia, psychiatric disorders, diabetes and cardiovascular disorders such as hypertension) in humans, domesticated companion animals and livestock animals. Pharmaceutical compositions and methods for treating such disorders are provided, as are methods for using such compounds for detecting NPY5 receptors.

  提供了能够调节NPY5受体活性的替代螺环[异苯并呋喃-1,4′-哌啶]-3-酮和3H-螺环异苯并呋喃-1,4′-哌啶。这些化合物可用于在体内或体外调节NPY5受体的配体结合，并且在治疗各种疾病（例如，肥胖或暴食症等进食障碍、精神障碍、糖尿病和高血压等心血管疾病）方面对人类、驯养的伴侣动物和家畜动物特别有用。提供了用于治疗这些疾病的药物组合物和方法，以及用于检测NPY5受体的这些化合物的方法。
• Spiro[isobenzofuran-1,4'-piperidin]-3-ones and 3h-spiroisobenzofuran-1,4'-piperidines
  申请人：Bakthavatchalam Rajagopal

  公开号：US20050033048A1

  公开（公告）日：2005-02-10

  Substituted spiro[isobenzofuran-1,4′-piperidin]-3-ones and 3H-spiroisobenzofuran-1,4′-piperidines capable of modulating NPY5 receptor activity are provided. Such compounds may be used to modulate ligand binding to NPY5 receptors in vivo or in vitro, and are particularly useful in the treatment of a variety of disorders (e.g., eating disorders such as obesity or bulimia, psychiatric disorders, diabetes and cardiovascular disorders such as hypertension) in humans, domesticated companion animals and livestock animals. Pharmaceutical compositions and method for treating such disorders are provided, as are methods for using such compounds for detecting NPY5 receptors.

  本文提供了能够调节NPY5受体活性的取代的spiro[异苯并呋喃-1,4'-哌啶]-3-酮和3H-spiro异苯并呋喃-1,4'-哌啶。这些化合物可以用于体内或体外调节NPY5受体的配体结合，并且在人类、宠物和家畜动物的多种疾病治疗中特别有用（例如，饮食失调如肥胖症或贪食症、精神障碍、糖尿病和心血管疾病如高血压）。提供了制药组合物和治疗这些疾病的方法，以及使用这些化合物检测NPY5受体的方法。
• CERTAIN CHEMICAL ENTITIES, COMPOSITIONS, AND METHODS
  申请人：YANG Zhe

  公开号：US20090253737A1

  公开（公告）日：2009-10-08

  Provided are certain chemical entities, and methods of use to modulate skeletal myosin, skeletal actin, skeletal tropomyosin, skeletal troponin C, skeletal troponin I, skeletal troponin T, and skeletal muscle, including fragments and isoforms thereof, as well as the skeletal sarcomere, and methods of use in the treatment of neuromuscular disorders, conditions having muscle wasting, claudication, frailty, metabolic syndrome, muscle atrophy associated with disuse, and muscle fatigue, and other indications.

  提供了某些化学实体及其使用方法，以调节骨骼肌肌球蛋白、骨骼肌肌动蛋白、骨骼肌肌肌纤维蛋白、骨骼肌肌钙蛋白C、骨骼肌肌钙蛋白I、骨骼肌肌钙蛋白T和骨骼肌，包括其片段和亚型，以及骨骼肌肌节段，并用于治疗神经肌肉疾病、肌肉萎缩、跛行、虚弱、代谢综合征、与不使用有关的肌肉萎缩和肌肉疲劳以及其他适应症的方法。
• CERTAIN CHEMICAL ENTITIES, COMPOSITIONS AND METHODS
  申请人：Yang Zhe

  公开号：US20110312975A1

  公开（公告）日：2011-12-22

  Provided are certain chemical entities, and methods of use to modulate skeletal myosin, skeletal actin, skeletal tropomyosin, skeletal troponin C, skeletal troponin I, skeletal troponin T, and skeletal muscle, including fragments and isoforms thereof, as well as the skeletal sarcomere, and methods of use in the treatment of neuromuscular disorders, conditions having muscle wasting, claudication, frailty, metabolic syndrome, muscle atrophy associated with disuse, and muscle fatigue, and other indications.

  提供了某些化学实体和使用方法，以调节骨骼肌肌球蛋白、骨骼肌肌动蛋白、骨骼肌肌肽、骨骼肌肌钙蛋白C、骨骼肌肌钙蛋白I、骨骼肌肌钙蛋白T和骨骼肌，包括其片段和亚型，以及骨骼肌肌节，以及在治疗神经肌肉疾病、肌肉消耗症、跛行、虚弱、代谢综合症、与不使用相关的肌肉萎缩和肌肉疲劳等症状的使用方法。
• Spiro [isobenzofuran-1,4'piperidin]-3-ones and 3H-spiroisobenzofuran-1, 4'-piperidines
  申请人：NEUROGEN CORPORATION

  公开号：EP1695977A2

  公开（公告）日：2006-08-30

  This invention relates generally to substituted spiro[isobenzofuran-1,4'-piperidin]-3-ones and 3H-spiroisobenzofuran-1,4'-piperidines that are modulators of mammalian neuropeptide Y5 (NPY5) receptors, and to the use of such compounds for treating a variety of physiological disorders associated with NPY5 receptor activation, such as feeding disorders, psychiatric disorders and cardiovascular diseases. The invention further relates to the use such compounds as probes for the detection and localization of NPY5 receptors.

  本发明一般涉及取代的螺[异苯并呋喃-1,4'-哌啶]-3-酮和3H-螺异苯并呋喃-1,4'-哌啶，它们是哺乳动物神经肽Y5（NPY5）受体的调节剂，本发明还涉及使用此类化合物治疗与NPY5受体激活有关的各种生理紊乱，如进食紊乱、精神紊乱和心血管疾病。本发明进一步涉及将此类化合物用作检测和定位 NPY5 受体的探针。