sodium 3-(methoxycarbonyl)-4-oxo-1,4,5,6-tetrahydropyridin-2-olate

• 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: sodium 3-(methoxycarbonyl)-4-oxo-1,4,5,6-tetrahydropyridin-2-olate
• 英文别名: sodium;5-methoxycarbonyl-4-oxo-2,3-dihydro-1H-pyridin-6-olate
• 化学式: C₇H₈NO₄*Na
• 分子量: 193.135
• InChiKey: AVFRJKJFAKCHNJ-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -4.7
• 重原子数：
  13.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  78.46
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  sodium 3-(methoxycarbonyl)-4-oxo-1,4,5,6-tetrahydropyridin-2-olate 在 盐酸 、 ammonium acetate 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 3.5h， 生成 2-(2-氯吡啶-4-基)-1,5,6,7-四氢-4H-吡咯并[3,2-c]吡啶-4-酮
  参考文献：
  名称：

  Pyrrolopyridine Inhibitors of Mitogen-Activated Protein Kinase-Activated Protein Kinase 2 (MK-2)

  摘要：

  A new class of potent kinase inhibitors selective for mitogen-activated protein kinase-activated protein kinase 2 (MAPKAP-K2 or MK-2) for the treatment of rheumatoid arthritis has been prepared and evaluated. These inhibitors have IC50 values as low as 10 nM against the target and have good selectivity profiles against a number of kinases including CDK2, ERK, JNK, and p38. These MK-2 inhibitors have been shown to suppress TNF alpha production in U397 cells and to be efficacious in an acute inflammation model. The structure-activity relationships of this series, the selectivity for MK-2 and their activity in both in vitro and in vivo models are discussed. The observed selectivity is discussed with the aid of an MK-2/inhibitor crystal structure.

  DOI：

  10.1021/jm0611004
• 作为产物：
  描述：

  氨甲酸,(3-甲基-6-羰基-1-环己烯-1-基)-,甲基酯(9CI) 在 sodium methylate 作用下， 以 甲苯 为溶剂， 反应 1.5h， 生成 sodium 3-(methoxycarbonyl)-4-oxo-1,4,5,6-tetrahydropyridin-2-olate
  参考文献：
  名称：

  一种2,4-哌啶二酮的合成方法

  摘要：

  本发明公开了一种2,4-哌啶二酮合成方法，该方法以丙二酸单甲酯和3-氨基丙酸甲酯盐酸盐或3-氨基丙酸乙酯盐酸盐为初始原料，以二氯甲烷为溶剂、二环己基碳二亚胺（DDC）作为脱水剂、三乙胺为缚酸剂的条件下反应，酰化缩合产物甲基-3-((3-甲氧基-3-羰基丙基)氨基)-3-羰基丙酸酯，在酰化缩合反应过程中以鎓盐类作为催化剂，该催化剂选择性好、副反应少、收率更高。然后在甲醇钠的作用下合环缩成3-(甲酯基（甲氧羰基）)-4-羰基-1,4,5,6-四氢吡啶-2-醇酸钠，再在盐酸体系中脱羧成2,4-哌啶二酮，整个反应中，由于甲氧基容易脱去，反应原料易得，反应条件温和，操作安全且转化率高。

  公开号：

  CN103936666B

文献信息

• Extending the Scope of the Aza-Fischer Synthesis of 4- and 6-Azaindoles
  作者：David Thomae、Matthieu Jeanty、Jérome Coste、Gérald Guillaumet、Franck Suzenet

  DOI：10.1002/ejoc.201300167

  日期：2013.6

  Fischer indole cyclization has recently been described as an efficient approach to the synthesis of azaindoles bearing electron-donating groups. We now show that this cascade reaction can be very efficient for the formation of a wider range of 4- and 6-azaindoles by using microwave irradiation.

  Fischer 吲哚环化最近被描述为合成带有给电子基团的氮杂吲哚的有效方法。我们现在表明，通过使用微波辐射，这种级联反应可以非常有效地形成更广泛的 4- 和 6-氮杂吲哚。
• Mitogen activated protein kinase-activated protein kinase-2 inhibiting compounds
  申请人：Pharmacia Corporation

  公开号：US20040209897A1

  公开（公告）日：2004-10-21

  Compounds are described which inhibit mitogen activated protein kinase-activated protein kinase-2 (MK-2). Methods of using such compounds for the inhibition of MK-2, and for the prevention or treatment of a disease or disorder that is mediated by TNF&agr;, are described, where the method involves administering to the subject an MK-2 inhibiting compound of the present invention. Therapeutic compositions, pharmaceutical compositions and kits which contain the present MK-2 inhibiting compounds are also described.

  本文描述了抑制有丝分裂原活化蛋白激酶激活蛋白激酶-2（MK-2）的化合物。本文还描述了使用这些化合物来抑制MK-2并预防或治疗由TNFα介导的疾病或障碍的方法，其中该方法涉及向受试者施用本发明的MK-2抑制化合物。本文还描述了包含本MK-2抑制化合物的治疗组合物、制药组合物和试剂盒。
• Beta-carboline compounds and analogues thereof as mitogen-activated protein kinase-activated protein kinase-2 inhibitors
  申请人：Anderson R. David

  公开号：US20050137220A1

  公开（公告）日：2005-06-23

  A method is described for inhibiting mitogen activated protein kinase-activated protein kinase-2 in a subject in need of such inhibition, where the method involves administering to the subject a beta-carboline MK-2 inhibiting compound, or a pharmaceutically acceptable salt thereof.

  本文描述了一种用于抑制需要这种抑制的受试者中的有丝分裂原活化蛋白激酶激活蛋白激酶-2的方法，其中该方法涉及向受试者施用一种β-喀啉MK-2抑制化合物或其药学上可接受的盐。
• [EN] BETA-CARBOLINE COMPOUNDS AND ANALOGUES THEREOF AND THEIR USE AS MITOGEN-ACTIVATED PROTEIN KINASE-ACTIVATED PROTEIN KINASE-2 INHIBITORS<br/>[FR] COMPOSES DE BETA-CARBOLINE AINSI QUE LEURS ANALOGUES ET LEUR UTILISATION EN TANT QU'INHIBITEURS DE PROTEINE KINASE-2 ACTIVEE PAR PROTEINE KINASE ACTIVEE PAR DES MITOGENES
  申请人：PHARMACIA CORP

  公开号：WO2005009370A2

  公开（公告）日：2005-02-03

  Novel methods and compositions are described for inhibiting mitogen activated protein kinase-activated protein kinase-2 in a subject. The method involves administering to the subject a beta-carboline MK-2 inhibiting compound, or a pharmaceutically acceptable salt, or isomer thereof. The novel compositions are capable of inhibiting mitogen activated protein kinase-activated protein kinase-2 and analogues thereof. Pharmaceutical compositions and kits that include these compounds are also described.
• 一种2,4-哌啶二酮的合成方法
  申请人：甘肃省化工研究院

  公开号：CN103936666B

  公开（公告）日：2016-01-20

  本发明公开了一种2,4-哌啶二酮合成方法，该方法以丙二酸单甲酯和3-氨基丙酸甲酯盐酸盐或3-氨基丙酸乙酯盐酸盐为初始原料，以二氯甲烷为溶剂、二环己基碳二亚胺（DDC）作为脱水剂、三乙胺为缚酸剂的条件下反应，酰化缩合产物甲基-3-((3-甲氧基-3-羰基丙基)氨基)-3-羰基丙酸酯，在酰化缩合反应过程中以鎓盐类作为催化剂，该催化剂选择性好、副反应少、收率更高。然后在甲醇钠的作用下合环缩成3-(甲酯基（甲氧羰基）)-4-羰基-1,4,5,6-四氢吡啶-2-醇酸钠，再在盐酸体系中脱羧成2,4-哌啶二酮，整个反应中，由于甲氧基容易脱去，反应原料易得，反应条件温和，操作安全且转化率高。