2-cyano-N'-(2-cyanoacetyl)acetohydrazide | 73673-39-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-cyano-N'-(2-cyanoacetyl)acetohydrazide
• 英文别名: 2-cyano-N’-(2-cyanoacetyl)acetohydrazide
• CAS: 73673-39-9
• 化学式: C₆H₆N₄O₂
• mdl: MFCD00127182
• 分子量: 166.139
• InChiKey: KBBHBYYQAYSQQA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  106
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-cyano-N'-(2-cyanoacetyl)acetohydrazide 在 盐酸 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 3.0h， 生成 2-oxo-N'-(2-oxo-7-(phenyldiazenyl)-2H-chromene-3-carbonyl)-7-(phenyl diazenyl)-2H-chromene-3-carbohydrazide
  参考文献：
  名称：

  Design, green one-pot synthesis and molecular docking study of novel N,N-bis(cyanoacetyl)hydrazines and bis-coumarins as effective inhibitors of DNA gyrase and topoisomerase IV

  摘要：

  A novel, quick, environmentally safe, and one-pot synthesis of a series of N,N-bis(cyanoacetyl)hydrazine derivatives, bis-imino-2H-chromenes and bis-2-oxo-2H-chromene derivatives have been designed. Some selected newly synthesized compounds were investigated in vitro for their antibacterial activity. Compound 5j is the most toxic compound against Staphylococcus aureus with activity index 171%, followed by compound 15b with activity index 136% compared to standard drug ampicillin. Moreover, compound 15a is the most toxic compound against Escherichia coli with activity index 111% compared to standard drug gentamicin. Minimum inhibitory concentration (MIC) was carried out for compounds with high antibacterial activity. Compound 5j has good MIC (7.8 mu g/ml) against Staphylococcus aureus while 15a has good MIC (31.25 mu g/ml) against Streptococcus mutans which is better than MIC of the standard drug ampicillin (MIC = 62.5 mu g/ml). Compounds 5j, 5k, 15a, 15b and 15e which have good MIC values were introduced to enzyme assay against DNA gyrase and topoisomerase IV. The results showed that compound 15a can strongly inhibit DNA gyrase and topoisomerase IV (IC50 = 27.30 and 25.52 mu M respectively), compared to methotrexate as the standard drug (IC50 = 29.01 and 23.55 mu M respectively). Structure-activity relationships were also discussed based on the biological and docking simulation results.

  DOI：

  10.1016/j.bioorg.2020.103672
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 碘 作用下， 生成 2-cyano-N'-(2-cyanoacetyl)acetohydrazide
  参考文献：
  名称：

  v. Rothenburg, Chemische Berichte, 1894, vol. 27, p. 691

  摘要：

  DOI：

文献信息

• Synthesis and characterization for novel VO(II) complexes from cyanoacetohydrazide-based ligands; Hirshfeld crystals, DFT study and biodiesel catalytic synthesis from waste frying oil
  作者：Asmaa A. Kurdi、Moataz Morad、Hana M. Abumelha、Kholood Alkhamis、Meshari M. Aljohani、Gaber A.M. Mersal、Nashwa El-Metwaly

  DOI：10.1016/j.molstruc.2021.130603

  日期：2021.9

  Two new VO(II) complexes have been synthesized from ligands based on cyanoacetohydrazide (H2L1 & H2L2). Variable analytical and spectral methods have elucidated these complexes as well as their original ligands. IR, 1H NMR, UV-Vis, Mass, EPR, SEM, EDX, XRD and elemental analysis were the practical techniques applied for characterization. Binegative tetradentate mode was suggested within (VO)2-L1 complex

  从基于氰基乙酰肼（H 2 L 1和H 2 L 2）的配体合成了两种新的VO（II）配合物。可变分析和光谱方法阐明了这些复合物及其原始配体。IR，1 H NMR，UV-Vis，质量，EPR，SEM，EDX，XRD和元素分析是用于表征的实用技术。在（VO）2 -L 1络合物中建议采用二齿四齿模式，而在（VO）2 -H 2 L 2中建议采用中性四齿模式。复杂的。根据VU-Vis光谱和EPR光谱，提出络合物的几何形状为方锥形式。为了优化它们的结构形式并提取关键的量子参数，在化合价双-zeta极化碱基组（6-31G *）下引入了DFT分析。提取的物理参数表明，（VO）2 -L 1配合物具有优异的特性。另一方面，Hirshfeld的表面性质表明其独特的晶体性质。因此，选择了（VO）2 -L 1配合物，以通过以下途径催化生物柴油的合成：废煎炸油进行酯交换过程。特别地，由于缺乏Cd和Pb金属，合成生物燃料
• Synthesis, Antioxidant and Antiproliferative Evaluation, Molecular Docking and DFT Studies of Some Novel Coumarin and Fused Coumarin Derivatives
  作者：Mustafa A. S. Gouda、Mounir A. I. Salem、Magda I. Marzouk、Naglaa F. H. Mahmoud、Mahmoud F. Ismail

  DOI：10.1002/cbdv.202300706

  日期：2023.7

  synthesize novel coumarin and heterocycle-fused coumarin derivatives. The chemical structures of all the new coumarin compounds were identified by spectral analyses. Some of the new coumarins compounds were screened in human cancer cell lines (HEPG-2, MCF-7, HCT-116 and PC-3) to learn about their cytotoxic effects in addition to the study of their DNA damage and antioxidant activity. Three of these

  通过 4-Chloro-2-oxo-2 H 的缩合，以优异的产率合成了 N' -[(4-Chloro-2-oxo-2 H -chromen - 3 -yl) 亚甲基]-2-氰基乙酰肼 ( 3 ) -色烯-3-甲醛与氰基乙酰肼。化合物3被用作合成新型香豆素和杂环稠合香豆素衍生物的结构单元。通过光谱分析鉴定了所有新香豆素化合物的化学结构。在人类癌细胞系（HEPG-2、MCF-7、HCT-116 和 PC-3）中筛选了一些新的香豆素化合物，除了研究其 DNA 损伤和抗氧化活性外，还了解其细胞毒性作用。其中三种化合物表现出显着的抗氧化和抗增殖活性。此外，它们能够保护 DNA 免受博莱霉素引起的损伤。对这些化合物进行了体外分子对接、DFT 和分子静电势研究。
• Ried,W.; Koecher,E.-U., Justus Liebigs Annalen der Chemie, 1961, vol. 647, p. 116 - 144
  作者：Ried,W.、Koecher,E.-U.

  DOI：——

  日期：——
• Ried; Schleimer, Justus Liebigs Annalen der Chemie, 1959, vol. 626, p. 106,112
  作者：Ried、Schleimer

  DOI：——

  日期：——
• Investigation of Pyrazole Compounds. II.¹ The Synthesis of 1-Phenyl-3-hydroxy-5-pyrazolone Imide
  作者：A. Weissberger、H. D. Porter

  DOI：10.1021/ja01241a017

  日期：1943.1