5-氰基-2-甲基-6-氧代-1H-吡啶-3-羧酸甲酯 | 71408-02-1

• 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
• 中文名称: 5-氰基-2-甲基-6-氧代-1H-吡啶-3-羧酸甲酯
• 中文别名: 5-氰基-6-羟基-2-甲基烟酸甲酯
• 英文名称: 5-cyano-2-methyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid methyl ester
• 英文别名: methyl 5-cyano-2-methyl-6-oxo-1,6-dihydropyridine-3-carboxylate；SF397；5-cyano-2-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid methyl ester；Methyl 3-cyano-6-methyl-2-pyridone-5-carboxylate；Methyl 5-cyano-6-hydroxy-2-methylnicotinate；methyl 5-cyano-2-methyl-6-oxo-1H-pyridine-3-carboxylate
• CAS: 71408-02-1
• 化学式: C₉H₈N₂O₃
• mdl: MFCD00973780
• 分子量: 192.174
• InChiKey: CONOYSKOLFZPBL-UHFFFAOYSA-N

物化性质

• 熔点：
  >250°C

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  79.2
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2933399090

反应信息

• 作为反应物：
  描述：

  5-氰基-2-甲基-6-氧代-1H-吡啶-3-羧酸甲酯 在 五氯化磷 、 三氯氧磷 作用下， 反应 24.0h， 以68%的产率得到6-氯-5-氰基-2-甲基烟酸甲酯
  参考文献：
  名称：

  COMPOUNDS AND METHODS for the inhibition of HDAC

  摘要：

  公开号：

  EP2533783B1
• 作为产物：
  描述：

  氰乙酰胺 生成 5-氰基-2-甲基-6-氧代-1H-吡啶-3-羧酸甲酯
  参考文献：
  名称：

  STOUT, D. M.;JAMAMOTO, D. M.;BARSELON-JANG, C.

  摘要：

  DOI：

文献信息

• Synthesis of 2,3,5,6-Tetrasubstituted Pyridines from Enamines Derived from N,N-Dimethylformamide Dimethyl Acetal
  作者：Fathi A. Abu-Shanab、Alan D. Redhouse、J. Robin Thompson、Basil J. Wakefield

  DOI：10.1055/s-1995-3954

  日期：1995.5

  Reactions of 1,3-dicarbonyl compounds with N,N-dimethylformamide dimethyl acetal, followed by cyanothioacetamide or cyanoacetamide and sodium hydride, then acidification, give 5,6-disubstituted 3-cyanopyridine-2(1H)-thiones or 5,6-disubstituted 3-cyanopyridin-2(1H)-ones 4. Analogous reactions with the malono-nitrile dimer give 5,6-disubstituted 3-cyano-2-(dicyanomethylene)-1,2-dihydropyridines 9.

  1,3-二羰基化合物与N,N-二甲基甲酰胺二甲基缩醛反应，再与氰基硫代乙酰胺或氰基乙酰胺与氢化钠反应，然后酸化，得到5,6-二取代的3-氰基吡啶-2(1H)-硫酮或5,6-二取代的 3-氰基吡啶-2(1H)-酮 4. 与丙二腈二聚体进行类似反应，得到 5,6-二取代的 3-氰基-2-(二氰基亚甲基)-1,2-二氢吡啶 9。
• COMPOUNDS AND METHODS
  申请人：Baloglu Erkan

  公开号：US20130059883A1

  公开（公告）日：2013-03-07

  Disclosed are compounds having the formula: wherein X 1 , X 2 , X 3 , R 1 , R 2 , R 3 , R 4 , Y, A, Z, L and n are as defined herein, and methods of making and using the same.

  公开的化合物具有以下公式：其中X1，X2，X3，R1，R2，R3，R4，Y，A，Z，L和n的定义如下，以及制备和使用它们的方法。
• Compounds and methods
  申请人：Baloglu Erkan

  公开号：US08901156B2

  公开（公告）日：2014-12-02

  Disclosed are compounds having the formula: wherein X1, X2, X3, R1, R2, R3, R4, Y, A, Z, L and n are as defined herein, and methods of making and using the same.

  本文披露了具有以下式子的化合物： 其中X1、X2、X3、R1、R2、R3、R4、Y、A、Z、L和n的定义如本文所述，并且还披露了制备和使用这些化合物的方法。
• Fossa; Boggia; Lo Presti, Il Farmaco, 1997, vol. 52, # 8-9, p. 523 - 530
  作者：Fossa、Boggia、Lo Presti、Mosti、Dorigo、Floreani

  DOI：——

  日期：——
• Synthesis, Inhibitory Activity of Cholinesterases, and Neuroprotective Profile of Novel 1,8-Naphthyridine Derivatives
  作者：Cristóbal de los Ríos、Javier Egea、José Marco-Contelles、Rafael León、Abdelouahid Samadi、Isabel Iriepa、Ignacio Moraleda、Enrique Gálvez、Antonio G. García、Manuela G. López、Mercedes Villarroya、Alejandro Romero

  DOI：10.1021/jm901902w

  日期：2010.7.22

  1,8-Naphthyridine derivatives related to 17 (ITH4012), a neuroprotective compound reported by our research group, have been synthesized. In general, they have shown better inhibition of acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) than most tacrine derivatives previously synthesized in our laboratory. The compounds presented an interesting neuroprotective profile in SH-SY5Y neuroblastoma cells stressed with rotenone/oligomycin A. Moreover, compound 14 (ethyl 5-amino-2-methy1-6,7,8,9-tetrahydrobenzo[b][1,8]naphthyridine-3-carboxylate) also caused protection in cells stressed with okadaic acid (OA) or amyloid beta 1-42 peptide (A beta(1-42)). Interestingly, compound 14 prevented the OA-induced PP2A inhibition, one of the enzymes implicated in tau dephosphorylation. This compound also exhibited neuroprotection against neurotoxicity elicited by oxygen and glucose deprivation in hippocampal slices. Because these stressors caused neuronal damage related to physiopathological hallmarks found in the brain of Alzheimer's disease (AD) patients, we conclude that compound 14 deserves further in vivo studies in AD models to test its therapeutic potential in this disease.