2-cyano-N-(4-methylpyridin-2-yl)acetamide | 132371-14-3

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-cyano-N-(4-methylpyridin-2-yl)acetamide
• 英文别名: N-(4-methylpyridin-2-yl)cyanoacetamide；N-(4-methylpyrid-2-yl) cyanoacetamide；N-(4-Methyl-2-pyridyl)cyanoacetamide
• CAS: 132371-14-3
• 化学式: C₉H₉N₃O
• mdl: MFCD01344263
• 分子量: 175.19
• InChiKey: VBWZRNAQFLUSLN-UHFFFAOYSA-N

物化性质

• 熔点：
  108-109 °C
• 沸点：
  436.9±35.0 °C(Predicted)
• 密度：
  1.234±0.06 g/cm3(Predicted)

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

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：

  2-cyano-N-(4-methylpyridin-2-yl)acetamide 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 31.0h， 生成 N-(4-methylpyridin-2-yl)-2-(4-(piperidine-1-carbonyl)benzamido)thiophene-3-carboxamide
  参考文献：
  名称：

  发现新型噻吩-芳基酰胺衍生物作为具有强效抗分枝杆菌活性的 DprE1 抑制剂

  摘要：

  在这项研究中，我们报告了一系列新型噻吩-芳基酰胺化合物的设计和合成，这些化合物来源于非共价癸烯磷酰-β- d-核糖 2'-差向异构酶 (DprE1) 抑制剂 TCA1，通过基于结构的支架跳跃策略。噻吩核心侧翼的两条侧链的系统优化导致新的先导化合物带有噻吩-芳基酰胺支架，具有有效的抗分枝杆菌活性和低细胞毒性。化合物23j、24f、25a和25b在体外表现出有效对药物敏感（最小抑制浓度 (MIC) = 0.02–0.12 μg/mL）和耐药（MIC = 0.031–0.24 μg/mL）结核菌株的活性，同时保留有效的 DprE1 抑制（最大抑制浓度的一半（IC 50） ) = 0.2–0.9 μg/mL) 和良好的细胞内抗分枝杆菌活性。此外，这些化合物表现出良好的肝细胞稳定性和对人ether-à-go-go相关基因（hERG）通道的低抑制作用。具有可接受的药代动力学特性的代表性化合物25a在急

  DOI：

  10.1021/acs.jmedchem.1c00263
• 作为产物：
  描述：

  4-Amino-8-methyl-2H-pyrido<1,2-a>pyrimidin-2-one 150.0~155.0 ℃ 、133.32 Pa 条件下， 以80%的产率得到2-cyano-N-(4-methylpyridin-2-yl)acetamide
  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

• Designing, synthesis, and characterization of some novel coumarin derivatives as probable anticancer drugs
  作者：Darla Mark Manidhar、Rajesh Kumar Kesharwani、N. Bakthavatchala Reddy、C. Suresh Reddy、Krishna Misra

  DOI：10.1007/s00044-012-0299-0

  日期：2013.9

  activity. The chemical syntheses of 4-methyl-7-hydroxycoumarin and its 8-formyl derivative were carried out using Pechmann’s condensation followed by Duffs reaction. Treatment of the 8-formyl derivative with nine different N,N-di substituted cyanoacetamides in the presence of piperidine afforded the corresponding nine new 8-substituted-4-methyl-7-hydroxycoumarin derivatives. These compounds were characterized

  香豆素是具有多种医学性质的天然存在的氧杂环，因此用作设计新的有效类似物的先导化合物。基于含有香豆素核的抑制剂与人NAD（P）H：醌氧化还原酶-1和人磷酸二酯酶4B酶的复合物的X射线晶体结构，某些新型香豆素衍生物已被设计为专门用于胰腺癌的抑制剂。这两种酶在各种肿瘤中过表达，前者特别在胰腺癌中表达。通过电子药效团和对接研究进行的计算分析表明，4-甲基-7-羟基香豆素第8位的特定基团具有抗小鼠皮肤癌的抗癌活性，并可以增强抗肿瘤活性。使用Pechmann缩合然后进行Duffs反应进行4-甲基-7-羟基香豆素及其8-甲酰基衍生物的化学合成。用九种不同的方法处理8-甲酰基衍生物在哌啶存在下，N，N-二取代的氰基乙酰胺提供了相应的九种新的8-取代的-4-甲基-7-羟基香豆素衍生物。这些化合物的特征在于IR，1 H，1313 C NMR，质谱和元素分析。有趣的是，分子对接表明九种香豆素衍生物相对于香豆素本
• 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。
• Derivatives of the N-(pyrid-2-yl)amides of 3-aminocrotonic acid as chelating ligands
  作者：V. A. Dorokhov、S. V. Baranin、A. Dib、K. L. Cherkasova、M. N. Bochkareva、V. S. Bogdanov

  DOI：10.1007/bf01150906

  日期：1992.4

  New chelating ligands, N-(pyrid-2-yl)amides of 4,4,4-trichloro-3-amino-2-cyanocrotonic acid have been synthesized from N-(pyrid-2-yl)amides of cyanoacetic acid and CCl3CN. It has been demonstrated that by the action of butylthiodibutylborane they form binuclear boron chelate complexes. Analogous chelates have also been obtained from the N-(pyrid-2-yl)amides of acetoacetic and 4,4,4-trichloro-3-aminocrotonic acids.
• N-hetaryl-2-cyanoacetamides in the synthesis of substituted (E)-N-hetaryl-2-cyanoacrylamides, (E)-N-alkyl-N-hetaryl-2-cyanoacrylamides, and 6-amino-2-oxo-4-phenyl-1-(pyridin-2-yl)-1,2-dihydropyridine-3,5-dicarbonitriles
  作者：I. V. Dyachenko、V. D. Dyachenko、E. B. Rusanov

  DOI：10.1134/s1070428007010101

  日期：2007.1

  Knoevenagel condensation of N-hetaryl-substituted cyanoacetamides with aldehydes gave the corresponding (E)-N-hetaryl-2-cyanoacrylamides which were converted into (E)-N-alkyl-N-hetaryl-2-cyanoacrylamides and 6-amino-2-oxo-4-phenyl-1-(pyridin-2-yl)-1,2-dihydropyridine-3,5-dicarbonitriles. The structure of (E)-N-(pyridin-2-yl)-2-cyano-3-phenylprop-2-enamide was determined by X-ray analysis.
• Synthesis of boron chelates from N-(pyrid-2-YL)- and (N-4-methylpyrid-2-YL) cyanoacetamides and their tautomeric transformations
  作者：V. S. Bogdanov、S. V. Baranin、A. Dib、I. P. Yakovlev、V. A. Dorokhov

  DOI：10.1007/bf00959647

  日期：1991.1

  Chelate complexes in which the boron atom is bound to the pyridine N atom and the O atom of the deprotonated ligand were synthesized by reaction of N-(pyrid-2-yl)- and N-(4-methylpyrid-2-yl) cyanoacetamides. A new type of intrachelate tautomeric transformation was discovered: the complexes obtained can exist in solutions in the form of two tautomers, which are derivatives of acetimidic acid or the corresponding ketene N,O-acetals.