N-Cyanoacetimidsaeure-aethylester | 1558-82-3

• 物质功能分类: 化学试剂 - 有机试剂 - 酯类
• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 甲亚胺酸及其衍生物
• 英文名称: N-Cyanoacetimidsaeure-aethylester
• 英文别名: N-Cyanoacetimidsaure-athylester；ethyl (1Z)-N-cyanoethanimidate
• CAS: 1558-82-3
• 化学式: C₅H₈N₂O
• 分子量: 112.131
• InChiKey: PLVWUINOWYHRAA-ALCCZGGFSA-N

物化性质

• 熔点：
  78-81 °C(Solv: ethyl ether (60-29-7))
• 沸点：
  133.2±23.0 °C(Predicted)
• 密度：
  0.94

计算性质

• 辛醇/水分配系数(LogP)：
  0.92
• 重原子数：
  8.0
• 可旋转键数：
  1.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  45.38
• 氢给体数：
  0.0
• 氢受体数：
  3.0

安全信息

• 海关编码：
  2926909090
• 包装等级：
  III
• 危险类别：
  3
• 危险性防范说明：
  P501,P240,P210,P233,P243,P241,P242,P280,P370+P378,P303+P361+P353,P403+P235
• 危险品运输编号：
  3272
• 危险性描述：
  H225

制备方法与用途

用途：用于高效低毒农药啶虫脒的生产作为中间体。

反应信息

• 作为反应物：
  描述：

  N-Cyanoacetimidsaeure-aethylester 在 肼 作用下， 以 乙腈 为溶剂， 生成 3-氨基-5-甲基-4H-1,2,4-三唑
  参考文献：
  名称：

  Synthesis and Pharmacological Activity of Triazole Derivatives Inhibiting Eosinophilia

  摘要：

  In order to develop novel antiasthmatic agents based on a new mechanism of action, a series of 3-substituted 5-amino-1-[(methylamino)(thiocarbonyl)]-1H-1,2,4-triazole derivatives were synthesized and evaluated in a model in which eosinophilia was induced in the ah-way through intravenous (iv) injection of Sephadex particles on days 0, 2, and 5. After screening of several hundred derivatives, we finally identified the highly potent eosinophilia inhibitor 5-amino-3-(4-chlorophenyl)-1-[(methylamino)(thiocarbonyl)]-1H-triazole (23c, GCC-AP0341), which had ID50 values of 0.3 and 0.07 mg/kg when administered orally (os) and intraperitoneally tip), respectively. This compound showed complete inhibition of the hypersensitivity induced by ascaris inhalation at an ip dose of 1 mg/kg as well as low toxicity, with an LD(50) value of > 2.0 g/kg in mice. Extensive study of its mechanism of action revealed that 23c inhibited eosinophil survival induced by interleukin-5 (IL-5), but had little or no effect on leukotriene D-4 (LTD(4)) or platelet-activating factor (PAF)-induced responses. Taken together, these results suggest 23e as a novel candidate for the treatment of chronic asthma. Further studies are now underway.

  DOI：

  10.1021/jm9507993
• 作为产物：
  描述：

  氰胺 、 原乙酸三乙酯 在 乙酸酐 作用下， 生成 N-Cyanoacetimidsaeure-aethylester
  参考文献：
  名称：

  Synthesis and Pharmacological Activity of Triazole Derivatives Inhibiting Eosinophilia

  摘要：

  In order to develop novel antiasthmatic agents based on a new mechanism of action, a series of 3-substituted 5-amino-1-[(methylamino)(thiocarbonyl)]-1H-1,2,4-triazole derivatives were synthesized and evaluated in a model in which eosinophilia was induced in the ah-way through intravenous (iv) injection of Sephadex particles on days 0, 2, and 5. After screening of several hundred derivatives, we finally identified the highly potent eosinophilia inhibitor 5-amino-3-(4-chlorophenyl)-1-[(methylamino)(thiocarbonyl)]-1H-triazole (23c, GCC-AP0341), which had ID50 values of 0.3 and 0.07 mg/kg when administered orally (os) and intraperitoneally tip), respectively. This compound showed complete inhibition of the hypersensitivity induced by ascaris inhalation at an ip dose of 1 mg/kg as well as low toxicity, with an LD(50) value of > 2.0 g/kg in mice. Extensive study of its mechanism of action revealed that 23c inhibited eosinophil survival induced by interleukin-5 (IL-5), but had little or no effect on leukotriene D-4 (LTD(4)) or platelet-activating factor (PAF)-induced responses. Taken together, these results suggest 23e as a novel candidate for the treatment of chronic asthma. Further studies are now underway.

  DOI：

  10.1021/jm9507993

文献信息

• Notiz über die Reaktion von Methylhydrazin mit<i>N</i>-Cyano-azomethinen. Abhängigkeit des Reaktionsverlaufs von der Natur der Abgangsgruppe
  作者：Haukur Kristinsson、Tammo Winkler

  DOI：10.1002/hlca.19830660416

  日期：1983.6.15

  The reaction of methylhydrazine with N-cyanoazomethines 1 containing a thioalkyl leaving group yields the 3-amino-1,2,4-triazole derivatives 2, whereas the N-cyanoazomethines 1 containing an alkoxy leaving group give the isomeric 5-amino-1,2,4-triazoles 3. The yields are excellent and the position selectivity is high. The structures of the 1,2,4-triazole derivatives were determined with the aid of

  甲基肼与含有硫代烷基离去基团的N-氰基偶氮亚胺1的反应生成3-氨基-1,2,4-三唑衍生物2，而含有烷氧基离去基团的N-氰基偶氮亚胺1给出了异构体5-氨基-1， 2,4-三唑3.产率极高，位置选择性高。1,2,4-三唑衍生物的结构借助质子偶联的13 C-NMR确定。光谱。
• Synthese von [1,2,4]Triazolo [1,5-a]chinazolinen. Ableitung der Konformation von Substituenten mit Hilfe der13C-NMR.-Spektroskopie
  作者：Roland Heckendorn、Tammo Winkler

  DOI：10.1002/hlca.19800630102

  日期：1980.1.23

  Synthesis of [1,2,4]Triazolo[1,5-a]quinazolines. Assignment of the Conformation of Substituents with the Aid of 13C-NMR. Spectroscopy

  [1,2,4]三唑并[1,5- a ]喹唑啉的合成。借助13 C-NMR进行取代基构象的分配。光谱学
• Facile and Convenient Synthesis of 1‐Perfluoroalkyl‐1,2,4‐triazoles
  作者：M. Kammoun、A. Chihi、B. Hajjem、M. Bellassoued

  DOI：10.1080/00397910701651367

  日期：2007.12.1

  Abstract Treatment of N‐methylcarbonyl 1, N‐phenylthioamido 2, and N‐cyano 3 iminoethers with perfluoroalkylated hydrazines leads to 1‐perfluoroalkyl‐5‐methyl‐1,2,4‐ triazoles, 4,1‐perfluoroalkyl‐5‐phenylamino‐1,2,4‐triazoles 5, and 1‐perfluoroalkyl‐5‐amino‐1,2,4‐triazoles 6 in good yields. These compounds are screened for their biological activities.

  摘要 用全氟烷基化肼处理 N-甲基羰基 1、N-苯硫酰氨基 2 和 N-氰基 3 亚氨基醚生成 1-全氟烷基-5-甲基-1,2,4-三唑、4,1-全氟烷基-5-苯氨基- 1,2,4-三唑 5 和 1-全氟烷基-5-氨基-1,2,4-三唑 6 收率良好。筛选这些化合物的生物活性。
• Perez, Miguel A.; Soto, Jose L, Heterocycles, 1983, vol. 20, # 3, p. 463 - 468
  作者：Perez, Miguel A.、Soto, Jose L

  DOI：——

  日期：——
• HECKENDORN R.; WINKLER T., HELV. CHIM, ACTA, 1980, 63, NO 1, 1-9
  作者：HECKENDORN R.、 WINKLER T.

  DOI：——

  日期：——