N-(3-Methyl-2-pyridyl)cyanoacetamide | 122364-79-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-(3-Methyl-2-pyridyl)cyanoacetamide
• 英文别名: 2-cyano-N-(3-methylpyridin-2-yl)acetamide
• CAS: 122364-79-8
• 化学式: C₉H₉N₃O
• 分子量: 175.19
• InChiKey: MKWNEIDRHSCRBU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  65.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(3-Methyl-2-pyridyl)cyanoacetamide 在 三乙胺 作用下， 以 苯 为溶剂， 生成 4-Amino-9-methyl-2H-pyrido<1,2-a>pyrimidin-2-one
  参考文献：
  名称：

  High pressure synthesis of 4-amino-2-oxo-2H-pyrido[1,2-a]pyrimidines from 2-aminopyridines and ethyl cyanoacetate

  摘要：

  DOI：

  10.1007/bf00953744
• 作为产物：
  描述：

  4-Amino-9-methyl-2H-pyrido<1,2-a>pyrimidin-2-one 230.0 ℃ 、133.32 Pa 条件下， 以90%的产率得到N-(3-Methyl-2-pyridyl)cyanoacetamide
  参考文献：
  名称：

  Synthesis of N-(2-pyridyl)cyanoacetamides and 4-amino-2H-pyrido-[1,2-a]pyrimidin-2-ones from ethyl cyanoacetate and 2-aminopyridine

  摘要：

  The reaction of 2-aminopyridine and 2-aminopicolines with ethyl cyanoacetate under high pressures results in the formation of 4-amino-4H-pyrido[1,2-a]pyrimidin-2-ones. Depending on the structure of the initial pyridine base, heating of a mixture of the above reagents under low vacuum gives either the same products or their isomeric N-(2-pyridyl)cyanoacetamideBARs. The mutual transformations of the synthesized isomers were studied; it was found that cyanoacetamides are readily cyclized by the action of an alcoholic solution of HCl into pyrido[1,2-a]pyrimidin-2-ones, while the latter, during sublimation or heating in DMSO, undergo opening of the pyrimidine ring.

  DOI：

  10.1007/bf00958262

文献信息

• Evaluation of compound selectivity of aldo-keto reductases using differential scanning fluorimetry
  作者：Aurangazeb Kabir、Satoshi Endo、Naoki Toyooka、Mayuko Fukuoka、Kazuo Kuwata、Yuji O. Kamatari

  DOI：10.1093/jb/mvw063

  日期：——

  Inhibitors of AKR1B10 belonging to the aldo-keto reductase (AKR) superfamily are considered promising candidates for anti-cancer drugs. AKR1B1, a structurally similar isoform of AKR1B10, is involved in glucose metabolism. Thus, selective inhibition of AKR1B10 is required for the development of anti-cancer drugs. In this study, we first compared correlations between melting temperature and the 50% inhibition

  属于醛酮还原酶（AKR）超家族的AKR1B10抑制剂被认为是抗癌药物的有前途的候选药物。AKR1B1是AKR1B10的结构相似的同工型，参与葡萄糖代谢。因此，开发抗癌药物需要选择性抑制AKR1B10。在这项研究中，我们首先比较了分别通过差示扫描荧光法（DSF）和酶抑制实验获得的熔融温度与50％抑制浓度之间的相关性，发现除了低溶解度的化合物外，还具有良好的相关性。该结果表明DSF方法可用于AKR超家族的药物筛选。然后，我们评估了它们作为针对所有七个主要人类AKR1家族蛋白抑制剂的选择性，并发现C18对AKR1B10最特异。
• High pressure synthesis of 4-amino-2-oxo-2H-pyrido[1,2-a]pyrimidines from 2-aminopyridines and ethyl cyanoacetate
  作者：V. A. Dorokhov、S. V. Baranin、G. A. Stashina、V. M. Zhulin

  DOI：10.1007/bf00953744

  日期：1989.1
• DOROXOV, V. A.;BARANIN, S. V.;DIB, A.;BOGDANOV, V. S.;YAKOVLEV, I. P.;STA+, IZV. AN CCCP. CEP. XIM.,(1990) N, S. 2107-2113
  作者：DOROXOV, V. A.、BARANIN, S. V.、DIB, A.、BOGDANOV, V. S.、YAKOVLEV, I. P.、STA+

  DOI：——

  日期：——
• DOROXOV, V. A.;BARANIN, S. V.;STASHINA, G. A.;ZHULIN, V. M., IZV. AN CCCP. CEP. XIM.,(1989) N 1, S. 211-212
  作者：DOROXOV, V. A.、BARANIN, S. V.、STASHINA, G. A.、ZHULIN, V. M.

  DOI：——

  日期：——
• Synthesis of N-(2-pyridyl)cyanoacetamides and 4-amino-2H-pyrido-[1,2-a]pyrimidin-2-ones from ethyl cyanoacetate and 2-aminopyridine
  作者：V. A. Dorokhov、S. V. Baranin、A. Dib、V. S. Bogdanov、I. P. Yakovlev、G. A. Stashina、V. M. Zhulin

  DOI：10.1007/bf00958262

  日期：1990.9

  The reaction of 2-aminopyridine and 2-aminopicolines with ethyl cyanoacetate under high pressures results in the formation of 4-amino-4H-pyrido[1,2-a]pyrimidin-2-ones. Depending on the structure of the initial pyridine base, heating of a mixture of the above reagents under low vacuum gives either the same products or their isomeric N-(2-pyridyl)cyanoacetamideBARs. The mutual transformations of the synthesized isomers were studied; it was found that cyanoacetamides are readily cyclized by the action of an alcoholic solution of HCl into pyrido[1,2-a]pyrimidin-2-ones, while the latter, during sublimation or heating in DMSO, undergo opening of the pyrimidine ring.