cyano-(4-methoxy-phenylhydrazono)-acetic acid ethyl ester | 51337-35-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: cyano-(4-methoxy-phenylhydrazono)-acetic acid ethyl ester
• 英文别名: Mesoxalsaeure-aethylester-nitril-(4-methoxy-phenylhydrazon)；Cyan-(4-methoxy-phenylhydrazono)-essigsaeure-aethylester；2-Cyanglyoxylsaeureethylester-4-methoxyphenylhydrazon；Ethyl-2-cyanglyoxylat-4-methoxyphenylhydrazon；Ethyl 2-cyano-2-[(4-methoxyphenyl)hydrazinylidene]acetate
• CAS: 51337-35-0
• 化学式: C₁₂H₁₃N₃O₃
• 分子量: 247.254
• InChiKey: TWYQKCVYLPBHNO-UHFFFAOYSA-N

物化性质

• 熔点：
  120 °C
• 沸点：
  362.0±44.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  83.7
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  cyano-(4-methoxy-phenylhydrazono)-acetic acid ethyl ester 在 lithium hydroxide 、 草酰氯 、 potassium carbonate 、 三氟乙酸 、 tin(ll) chloride 、 sodium nitrite 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 4-Amino-5-(4-bromo-2-fluoro-phenylcarbamoyl)-1-(4-methoxy-phenyl)-1H-pyrazole-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  Preparation of 1-(4-methoxyphenyl)-1H-pyrazolo[4,3-d]pyrimidin-7(6H)-ones as potent, selective and bioavailable inhibitors of coagulation factor Xa

  摘要：

  Previously, potent factor Xa inhibitors were described based on a pyrazole core. Modifications of the pyrazole core have provided additional novel, highly potent factor Xa inhibitors. This manuscript will describe the synthesis and biological activity of factor Xa inhibitors containing the 1H-pyrazolo[4,3-d]pyrimidin-7(6H)-one and related bicyclic cores. Many of these compounds are potent, selective, and orally bioavailable inhibitors of coagulation factor Xa. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.04.044
• 作为产物：
  描述：

  甲氧苯胺 在 盐酸 作用下， 生成 cyano-(4-methoxy-phenylhydrazono)-acetic acid ethyl ester
  参考文献：
  名称：

  Lax, Journal fur praktische Chemie (Leipzig 1954), 1901, vol. <2> 63, p. 11,12

  摘要：

  DOI：

文献信息

• Synthesis, Molecular Docking, and Biological Evaluation of Some Novel Bis‐heterocyclic Compounds Based <i>N</i> , <i>N</i> ′‐([1,1′‐biphenyl]‐4,4′‐diyl)bis(2‐cyanoacetamide) as Potential Anticancer Agents
  作者：Nadia Hanafy Metwally、Fathy Mohamed Abdelrazek、Salwa Magdy Eldaly

  DOI：10.1002/jhet.3290

  日期：2018.12

  Synthesis of unreported hitherto N,N′‐([1,1′‐biphenyl]‐4,4′‐diyl)bis(2‐cyanoacetamide) as a precursor to synthesize bis‐chromenes, bis‐thiazole derivatives, and bis‐pyridizines. The structures of the newly synthesized compounds were established by their elemental analyses and spectral data. Some of the newly synthesized compounds were tested for in vitro activity against hepatocellular carcinoma, human

  迄今为止未报道的N，N '-[[[1,1'-联苯] -4,4'-二基）双（2-氰基乙酰胺）的合成作为合成双色烯，双噻唑衍生物和双吡啶的前体。通过元素分析和光谱数据确定了新合成化合物的结构。与使用的标准抗肿瘤药物（阿霉素）相比，测试了一些新合成的化合物对肝细胞癌，人乳腺癌和人宫颈癌细胞系的体外活性，结果表明起始的N，N '-（ [1,1'-联苯] -4,4'-二基）双（2-氰基乙酰胺）比阿霉素对肝细胞癌和人宫颈癌的活性更强。
• Synthesis of 2-Aryl-1,2,3-triazoles by Oxidative Cyclization of 2-(Arylazo)ethene-1,1-diamines: A One-Pot Approach
  作者：Kseniya D. Gavlik、Svetlana G. Lesogorova、Ekaterina S. Sukhorukova、Julia O. Subbotina、Pavel A. Slepukhin、Enrico Benassi、Nataliya P. Belskaya

  DOI：10.1002/ejoc.201600256

  日期：2016.5

  A one-pot approach for the synthesis of 2-aryl-5-amino-1,2,3-triazoles is reported. This approach involves a tandem nucleophilic addition of alkylamines to hydrazonoyl cyanides and in situ oxidative cyclization of the resulting 2-(arylazo)ethene-1,1-diamines in the presence of copper(II) acetate and air. The described one-pot procedure is characterized by good yields, excellent selectivity, methodical

  报道了一种用于合成 2-芳基-5-氨基-1,2,3-三唑的一锅法。该方法涉及将烷基胺串联亲核加成到腙酰氰化物，并在乙酸铜 (II) 和空气存在下原位氧化环化所得 2-(芳基偶氮) 乙烯-1,1-二胺。所描述的一锅法的特点是产量高、选择性好、方法简单，并且使用容易获得的化学品。该方法应用于2-芳基-1,2,3-三唑的克级合成。
• Reaction of (chloro carbonyl) phenyl ketene with 5-amino pyrazolones: Synthesis, characterization and theoretical studies of 7-hydroxy-6-phenyl-3-(phenyldiazenyl)pyrazolo[1,5-a]pyrimidine-2,5(1H,4H)-dione derivatives
  作者：Mahboobeh Zahedifar、Razieh Razavi、Hassan Sheibani

  DOI：10.1016/j.molstruc.2016.07.043

  日期：2016.12

  Abstract New 7-hydroxy-6-phenyl-3-(phenyldiazenyl)pyrazolo[1,5- a ]pyrimidine-2,5(1 H ,4 H )-dione derivatives were synthesized from the reaction of (chlorocarbonyl)phenyl ketene and 5-amino pyrazolones in high to excellent yields and short reaction times. Structures of the new compounds were fully characterized by their spectral data IR, 1 H NMR, and 13 C NMR and by the theoretical results. Density

  摘要 由(氯羰基)苯基乙烯酮与(氯羰基)苯基乙烯酮反应合成了新的7-羟基-6-苯基-3-(苯基二氮烯基)吡唑并[1,5-a]嘧啶-2,5(1 H ,4 H)-二酮衍生物。 5-氨基吡唑啉酮以高到极好的收率和较短的反应时间。新化合物的结构通过其光谱数据 IR、 1 H NMR 和 13 C NMR 以及理论结果进行了充分表征。密度泛函理论 (DFT) 用于优化结构，计算所需产品的能量和振动频率 IR 和 1 H NMR 屏蔽张量。将理论结果与实验数据进行了比较。
• Voltammetric Studies on Some Arylhydrazones of α-Cyano Ketones and α-Cyano Esters
  作者：G. M. Abou-Elenien、N. A. Ismail、T. S. Hafez

  DOI：10.1246/bcsj.64.651

  日期：1991.2

  The redox characteristics of the title compounds are extensively studied using DC-, cyclic voltammetry, coulometry, and controlled potential electrolysis in benzonitrile at platinum electrodes. These compounds are oxidized in one-electron transfer process followed by deprotonation which leads to dimerization. The reduction process differs according to the nature of the compound and the electron-withdrawing power of the substituent in the α-position. They can be reduced in a single two electron or two one electron waves leading in both cases to saturation of the hydrazonic moiety.

  在苯腈中，通过直流、循环伏安法、库仑法和可控电位电解法对标题化合物的氧化还原特性进行了广泛研究。这些化合物在单电子转移过程中被氧化，随后发生脱质子化反应，导致二聚化。还原过程因化合物的性质和α位取代基的吸电子能力而异。它们可以通过单个双电子或两个单电子波进行还原，两种情况都会导致肼基部分饱和。
• Multi-component reactions for the synthesis of pyrazolo [1,5-a]quinoline derivatives together with their cytotoxic evaluations
  作者：Rafat M. Mohareb、Maher H.E. Helal、Amany E. Mayhoub、Amira E.M. Abdallah

  DOI：10.4314/bcse.v37i3.14

  日期：——

  ABSTRACT. A new approaches for the synthesis of novel pyrazolo[1,5-a]quinazoline 8a-f and pyrazolo[1,5-a]quinazolin-6-one 10a-s and 12a-s derivatives were obtained using 4-(2-phenylhydrazono)-4H-pyrazol-3-amine derivatives 5a-f via their multi-component reactions. The later pyrazole derivatives were prepared via arylhydrazone derivatives 3a-f. The structures of the synthesized compounds were established based on their respective analytical data. On the other hand, the cytotoxic effects of the synthesized compounds were obtained against the six cancer cell lines, namely A549, HT-29, MKN-45, U87MG, SMMC-7721 and, H460 utilizing foretinib as the positive control and the standard MTT assay in vitro. The obtained results showed that compounds 8c, 8f, 10c, 10i, 10l, 10p, 10s, 12c, 12i, 12l, 12p and, 12s were the most cytotoxic compounds. In most cases the presence of the electronegative Cl group enhanced the cytotoxicity of the tested compound.   KEY WORDS: Multi-component reactions, Pyrazolo[1,5-a]quinazoline, Pyrazolo[1,5-a]quinazolin-6-one, Cytotoxicity Bull. Chem. Soc. Ethiop. 2023, 37(3), 717-734.                                                                DOI: https://dx.doi.org/10.4314/bcse.v37i3.14

  摘要。使用 4-(2-苯肼基)-4H-吡唑-3-胺衍生物 5a-f 通过多组分反应合成了新型吡唑并[1,5-a]喹唑啉 8a-f 和吡唑并[1,5-a]喹唑啉-6-酮 10a-s 和 12a-s 衍生物。之后的吡唑衍生物是通过芳基腙衍生物 3a-f 制备的。根据各自的分析数据确定了合成化合物的结构。另一方面，以 foretinib 为阳性对照，采用标准 MTT 法，在体外测定了合成化合物对 A549、HT-29、MKN-45、U87MG、SMMC-7721 和 H460 六种癌细胞株的细胞毒性作用。结果表明，化合物 8c、8f、10c、10i、10l、10p、10s、12c、12i、12l、12p 和 12s 是细胞毒性最强的化合物。在大多数情况下，电负性 Cl 基团的存在增强了受试化合物的细胞毒性； ； 关键词：多组分反应 吡唑并[1,5-a]喹唑啉 吡唑并[1,5-a]喹唑啉-6-酮 细胞毒性 ； Bull.Chem.Soc. Ethiop.2023, 37(3), 717-734. ； DOI: https://dx.doi.org/10.4314/bcse.v37i3.14