methyl 5-(pyridin-3-yl)-1,3,4-oxadiazole-2-carboxylate | 849798-87-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: methyl 5-(pyridin-3-yl)-1,3,4-oxadiazole-2-carboxylate
• 英文别名: Methyl 5-(pyridin-3-yl)-[1,3,4]-oxadiazole-2-carboxylate；methyl 5-pyridin-3-yl-1,3,4-oxadiazole-2-carboxylate
• CAS: 849798-87-4
• 化学式: C₉H₇N₃O₃
• 分子量: 205.173
• InChiKey: MMEXAEXPBZXIPK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  78.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 5-(pyridin-3-yl)-1,3,4-oxadiazole-2-carboxylate 、 alkaline earth salt of/the/ methylsulfuric acid 生成 6-phenyl-1-[5-(pyridin-3-yl)-1,3,4-oxadiazol-2-yl]-hexan-1-one
  参考文献：
  名称：

  Discovery of an exceptionally potent and selective class of fatty acid amide hydrolase inhibitors enlisting proteome-wide selectivity screening: concurrent optimization of enzyme inhibitor potency and selectivity

  摘要：

  The concurrent implementation of a proteome-wide serine hydrolase selectivity screen with traditional efforts to optimize fatty acid amide hydrolase (FAAH) inhibition potency led to the expedited discovery of a new class of exceptionally potent (K-i < 300 pM) and unusually selective (> 100-fold selective) inhibitors. The iterative inhibitor design and evaluation with assistance of the selectivity screen served to differentiate otherwise indistinguishable inhibitors permitting the simultaneous optimization of potency and selectivity. Significantly, the simultaneous assessment of all potential competitive enzymes with the selectivity screen does not require the use of expressed or purified enzymes or a competitive substrate, no modification of the inhibitors is required, and the relative potency for competitive enzymes can be quantified (IC50's) including those that lack known substrates or function. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.12.085
• 作为产物：
  描述：

  Oxo-[N'-(pyridine-3-carbonyl)-hydrazino]-acetic acid methyl ester 在 三乙胺 、 对甲苯磺酰氯 作用下， 生成 methyl 5-(pyridin-3-yl)-1,3,4-oxadiazole-2-carboxylate
  参考文献：
  名称：

  Discovery of an exceptionally potent and selective class of fatty acid amide hydrolase inhibitors enlisting proteome-wide selectivity screening: concurrent optimization of enzyme inhibitor potency and selectivity

  摘要：

  The concurrent implementation of a proteome-wide serine hydrolase selectivity screen with traditional efforts to optimize fatty acid amide hydrolase (FAAH) inhibition potency led to the expedited discovery of a new class of exceptionally potent (K-i < 300 pM) and unusually selective (> 100-fold selective) inhibitors. The iterative inhibitor design and evaluation with assistance of the selectivity screen served to differentiate otherwise indistinguishable inhibitors permitting the simultaneous optimization of potency and selectivity. Significantly, the simultaneous assessment of all potential competitive enzymes with the selectivity screen does not require the use of expressed or purified enzymes or a competitive substrate, no modification of the inhibitors is required, and the relative potency for competitive enzymes can be quantified (IC50's) including those that lack known substrates or function. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.12.085

文献信息

• Oxadiazole ketone inhibitors of fatty acid amide hydrolase
  申请人：Boger L. Dale

  公开号：US20060100212A1

  公开（公告）日：2006-05-11

  Certain oxadiazole ketone compounds are useful as FAAH inhibitors. Such compounds may be used in pharmaceutical compositions and methods for the treatment of disease states, disorders, and conditions mediated by fatty acid amide hydrolase (FAAH) activity. Thus, the compounds may be administered to treat anxiety, pain, inflammation, sleep disorders, eating disorders, or movement disorders (such as MS).

  某些噁唑酮类化合物可用作FAAH抑制剂。这些化合物可以用于制备药物组合物和治疗由脂肪酸酰胺水解酶（FAAH）活性介导的疾病状态、障碍和病况的方法。因此，这些化合物可用于治疗焦虑、疼痛、炎症、睡眠障碍、进食障碍或运动障碍（如多发性硬化症）。
• OXADIAZOLE KETONE INHIBITORS OF FATTY ACID AMIDE HYDROLASE
  申请人：THE SCRIPPS RESEARCH INSTITUTE

  公开号：EP1812427A1

  公开（公告）日：2007-08-01
• US7351724B2
  申请人：——

  公开号：US7351724B2

  公开（公告）日：2008-04-01
• [EN] OXADIAZOLE KETONE INHIBITORS OF FATTY ACID AMIDE HYDROLASE<br/>[FR] INHIBITEURS OXADIAZOLE CETONE D'HYDROLASE D'AMIDE D'ACIDE GRAS
  申请人：SCRIPPS RESEARCH INST

  公开号：WO2006044617A1

  公开（公告）日：2006-04-27

  [EN] Certain oxadiazole ketone compounds are useful as FAAH inhibitors. Such compounds may be used in pharmaceutical compositions and methods for the treatment of disease states, disorders, and conditions mediated by fatty acid amide hydrolase (FAAH) activity. Thus, the compounds may be administered to treat anxiety, pain, inflammation, sleep disorders, eating disorders, or movement disorders (such as MS).
  [FR] Certains composés d'oxadiazole cétone sont utiles en tant qu'inhibiteurs d'hydrolase d'amide d'acide gras (FAAH). De tels composés peuvent être utilisés dans des compositions pharmaceutiques et des procédés destinés au traitement d'états, troubles et conditions pathologiques à médiation par l'activité d'hydrolase d'amide d'acide gras (FAAH). Ces composés peuvent donc être administrés pour traiter l'anxiété, la douleur, l'inflammation, des troubles du sommeil, des troubles de l'alimentation ou des troubles du mouvement (tels que la sclérose en plaques).