Methyl 3-[(3-hydroxypyridin-2-yl)carbamoyl]-5-nitrobenzoate | 1056562-53-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Methyl 3-[(3-hydroxypyridin-2-yl)carbamoyl]-5-nitrobenzoate
• CAS: 1056562-53-8
• 化学式: C₁₄H₁₁N₃O₆
• 分子量: 317.258
• InChiKey: YAMFJFQEKKAIMU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  134
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Methyl 3-[(3-hydroxypyridin-2-yl)carbamoyl]-5-nitrobenzoate 在 PPA 作用下， 以80%的产率得到3-nitro-5-(oxazolo[4,5-b]pyridin-2-yl)benzoic acid
  参考文献：
  名称：

  Discovery of oxazolo[4,5-b]pyridines and related heterocyclic analogs as novel SIRT1 activators

  摘要：

  SIRT1 is an NAD(+)-dependent protein deacetylase that appears to produce beneficial effects on metabolic parameters such as glucose and insulin homeostasis. Activation of SIRT1 by resveratrol ( 1) has been shown to modulate insulin resistance, increase mitochondrial content and prolong survival in lower organisms and in mice on a high fat diet. Herein, we describe the identification and SAR of a series of oxazolo[4,5-b]pyridines as novel small molecule activators of SIRT1 which are structurally unrelated to and more potent than resveratrol. (C) 2009 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2008.11.106
• 作为产物：
  描述：

  2-氨基-3-羟基吡啶 、 5-硝基间苯二甲酸单甲酯 在 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 作用下， 以90%的产率得到Methyl 3-[(3-hydroxypyridin-2-yl)carbamoyl]-5-nitrobenzoate
  参考文献：
  名称：

  Discovery of oxazolo[4,5-b]pyridines and related heterocyclic analogs as novel SIRT1 activators

  摘要：

  SIRT1 is an NAD(+)-dependent protein deacetylase that appears to produce beneficial effects on metabolic parameters such as glucose and insulin homeostasis. Activation of SIRT1 by resveratrol ( 1) has been shown to modulate insulin resistance, increase mitochondrial content and prolong survival in lower organisms and in mice on a high fat diet. Herein, we describe the identification and SAR of a series of oxazolo[4,5-b]pyridines as novel small molecule activators of SIRT1 which are structurally unrelated to and more potent than resveratrol. (C) 2009 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2008.11.106

文献信息

• Sirtuin modulating compounds
  申请人：Nunes J. Joseph

  公开号：US20070037809A1

  公开（公告）日：2007-02-15

  Provided herein are novel sirtuin-modulating compounds and methods of use thereof. The sirtuin-modulating compounds may be used for increasing the lifespan of a cell, and treating and/or preventing a wide variety of diseases and disorders including, for example, diseases or disorders related to aging or stress, diabetes, obesity, neurodegenerative diseases, cardiovascular disease, blood clotting disorders, inflammation, cancer, and/or flushing as well as diseases or disorders that would benfit from increased mitochondrial activity. Also provided are compositions comprising a sirtuin-modulating compound in combination with another therapeutic agent.

  本文提供了新型的sirtuin调节化合物及其使用方法。这些sirtuin调节化合物可用于增加细胞寿命，并治疗和/或预防各种疾病和疾病，包括与衰老或应激有关的疾病或疾病，糖尿病，肥胖症，神经退行性疾病，心血管疾病，血液凝块性疾病，炎症，癌症和/或红斑病，以及需要增加线粒体活性的疾病或疾病。还提供了包含sirtuin调节化合物和另一种治疗剂的组合物。
• SIRTUIN MODULATING COMPOUNDS
  申请人：Nunes Joseph J.

  公开号：US20120197013A1

  公开（公告）日：2012-08-02

  Provided herein are novel sirtuin-modulating compounds and methods of use thereof. The sirtuin-modulating compounds may be used for increasing the lifespan of a cell, and treating and/or preventing a wide variety of diseases and disorders including, for example, diseases or disorders related to aging or stress, diabetes, obesity, neurodegenerative diseases, cardiovascular disease, blood clotting disorders, inflammation, cancer, and/or flushing as well as diseases or disorders that would benefit from increased mitochondrial activity. Also provided are compositions comprising a sirtuin-modulating compound in combination with another therapeutic agent.

  本文提供了一种新颖的调节沉默信息调节因子（sirtuin）的化合物及其使用方法。这些调节sirtuin的化合物可用于延长细胞寿命，并用于治疗和/或预防多种疾病和障碍，包括与衰老或应激有关的疾病或障碍、糖尿病、肥胖症、神经退行性疾病、心血管疾病、血液凝结障碍、炎症、癌症和/或潮红，以及需要增加线粒体活性的疾病或障碍。还提供了包含sirtuin调节化合物与另一种治疗药物组合的组合物。
• N-Phenyl Benzamide Derivatives as Sirtuin Modulators
  申请人：Milburn Michael

  公开号：US20090163476A1

  公开（公告）日：2009-06-25

  Provided herein are novel sirtuin-modulating compounds and methods of use thereof. The sirtuin-modulating compounds may be used for increasing the lifespan of a cell, and treating and/or preventing a wide variety of diseases and disorders including, for example, diseases or disorders related to aging or stress, diabetes, obesity, neurodegenerative diseases, cardiovascular disease, blood clotting disorders, inflammation, cancer, and/or flushing as well as diseases or disorders that would benefit from increased mitochondrial activity. Also provided are compositions comprising a sirtuin-modulating compound in combination with another therapeutic agent.

  本文提供了新型的调节sirtuin的化合物及其使用方法。这些sirtuin调节化合物可用于延长细胞寿命，以及治疗和/或预防各种疾病和障碍，包括与衰老或压力有关的疾病或障碍、糖尿病、肥胖症、神经退行性疾病、心血管疾病、血液凝结障碍、炎症、癌症和/或潮红，以及可以受益于增加线粒体活性的疾病或障碍。还提供了包含sirtuin调节化合物与另一种治疗剂的组合物。
• Imidazo[2,1-b]thiazole derivatives as sirtuin modulators
  申请人：Sirtris Pharmaceuticals, Inc.

  公开号：EP2388263A1

  公开（公告）日：2011-11-23

  Provided herein are novel sirtuin-modulating compounds and methods of use thereof. The sirtuin-modulating compounds may be used for increasing the lifespan of a cell, and treating and/or preventing a wide variety of diseases and disorders including, for example, diseases or disorders related to aging or stress, diabetes, obesity, neurodegenerative diseases, cardiovascular disease, blood clotting disorders, inflammation, cancer, and/or flushing as well as diseases or disorders that would benfit from increased mitochondrial activity. Also provided are compositions comprising a sirtuin-modulating compound in combination with another therapeutic agent.

  本文提供了新型sirtuin调节化合物及其使用方法。sirtuin调节化合物可用于延长细胞寿命，治疗和/或预防多种疾病和失调，包括与衰老或压力、糖尿病、肥胖症、神经退行性疾病、心血管疾病、凝血障碍、炎症、癌症和/或潮红有关的疾病或失调，以及可从线粒体活性增强中获益的疾病或失调。此外，还提供了由sirtuin调节化合物与另一种治疗剂组合而成的组合物。
• Thiazolopyridine derivatives as sirtuin-modulators
  申请人：Sirtris Pharmaceuticals, Inc.

  公开号：EP2468752A1

  公开（公告）日：2012-06-27

  Provided herein are novel sirtuin-modulating compounds (XII) and (XIII). The sirtuin-modulating compounds may be used for increasing the lifespan of a cell, and treating and/or preventing a wide variety of diseases and disorders including, for example, diseases or disorders related to aging or stress, diabetes, obesity, neurodegenerative diseases, cardiovascular disease, blood clotting disorders, inflammation, cancer, and/or flushing as well as diseases or disorders that would benefit from increased mitochondrial activity. Also provided are compositions comprising a sirtuin-modulating compound in combination with another therapeutic agent.

  本文提供的是新型 sirtuin 调节化合物 (XII) 和 (XIII)。sirtuin调节化合物可用于延长细胞寿命，治疗和/或预防多种疾病和失调，包括与衰老或压力、糖尿病、肥胖症、神经退行性疾病、心血管疾病、凝血障碍、炎症、癌症和/或潮红有关的疾病或失调，以及可从线粒体活性增强中获益的疾病或失调。此外，还提供了由sirtuin调节化合物与另一种治疗剂组合而成的组合物。