cyano-acetic acid-(3-nitro-benzylidenehydrazide) | 4980-32-9

• 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-acetic acid-(3-nitro-benzylidenehydrazide)
• 英文别名: Cyan-essigsaeure-(3-nitro-benzylidenhydrazid)；2-cyano-N-[(3-nitrophenyl)methylideneamino]acetamide
• CAS: 4980-32-9
• 化学式: C₁₀H₈N₄O₃
• 分子量: 232.199
• InChiKey: UCRRDFDZZFMXHI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  111
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(bis(ethylthio)methylene)malononitrile 、 cyano-acetic acid-(3-nitro-benzylidenehydrazide) 在 potassium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 以82%的产率得到7-(ethylthio)-2-(3-nitrophenyl)-5-oxo-3,5-dihydro-[1,2,4]triazolo[1,5-a]pyridine-6,8-dicarbonitrile
  参考文献：
  名称：

  新型N-取代的4-乙基硫烷基-2-吡啶酮和三唑并吡啶的合成及抗菌性能评价

  摘要：

  设计和开发合成抗微生物药物的新方法是当前药物化学的重要目标。十六新颖ñ -取代的氨基，Ñ -arylsulfonylamino-和Ñ -芳基-4-乙硫基-2-吡啶酮合成。评价了化合物对四种真菌和八种细菌菌株的抗菌活性。抗菌结果表明，与所有其他新合成的化合物和各种标准化合物相比，化合物14b对多种细菌和真菌菌株具有出色的活性。三唑并[1,5- a ]吡啶10c和10e 对三种被测革兰氏阴性细菌显示出明显的活性。

  DOI：

  10.1007/s00044-018-2264-z
• 作为产物：
  描述：

  氰乙酰肼 、 间硝基苯甲醛 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 生成 cyano-acetic acid-(3-nitro-benzylidenehydrazide)
  参考文献：
  名称：

  7-氨基-2-芳基/杂芳基-5-氧代-5,8-二氢[1,2,4]三唑并[1,5-a]吡啶-6-腈：合成和腺苷受体结合研究。

  摘要：

  一系列新颖的7-氨基-5-氧代-2-取代的芳基/杂芳基-5,8-二氢[1,2,4]三唑[1,5 - a ]吡啶-6-腈（4a– 4吨）合成，其特征在于，评价向HA的结合亲和力和选择性1，HA 2A，HA 2B和HA 3腺苷受体（ARS）。在支架的三唑部分的2位带有苯环的化合物4a对hA 1 AR（K i hA 1  = 0.076μM，hA 2A  = 25.6μM和hA 3）具有高亲和力和选择性 > 100μM）。在苯环的不同位置引入各种给电子和吸电子基团，导致对所有AR的亲和力和选择性大大降低，除了在2位带有4-羟基苯基的化合物4b。有趣的是，用较小的杂环噻吩环取代苯环（π过量的体系）导致对化合物4t的hA 1 AR的亲和力进一步提高（K i hA 1  = 0.051μM，hA 2A  = 9.01μM和hA 3  > 13.9μM），同时保留了对所有其他类似于化合物4a的AR亚型的

  DOI：

  10.1111/cbdd.13528

文献信息

• Facile isocyanide-based one-pot three-component regioselective synthesis of highly substituted pyridin-2(1H)-one derivatives at ambient temperature
  作者：Ming Li、Wei Kong、Li-Rong Wen、Fang-Hui Liu

  DOI：10.1016/j.tet.2012.03.124

  日期：2012.6

  A novel one-pot three-component regioselective synthesis of highly substituted pyridin-2-one derivatives starting from simple and readily available starting materials is described. The reactive zwitterionic intermediate generated by the addition of an isocyanide to dimethyl acetylenedicarboxylate (DMAD) was trapped with N-arylidene-2-cyanoacetohydrazides to afford the title compounds in moderate to

  描述了一种从简单易得的起始原料开始的高度取代的吡啶-2-酮衍生物的新颖的一锅三组分区域选择性合成。通过在N-亚芳基-2-氰基乙酰肼中捕获N，亚芳基-2-氰基乙酰肼，将通过向乙炔基二羧酸二甲酯（DMAD）中添加异氰化物而生成的反应性两性离子中间体，在不使用任何催化剂和其他添加剂的情况下以中等至良好的收率得到标题化合物。
• Synthese einiger neuer Hydrazone des Cyanessigsäurehydrazids und Isonicotinsäurehydrazids. 8. Mitteilung über Synthese tuberkulostatischer Substanzen
  作者：Josef Klosa

  DOI：10.1002/ardp.19562890404

  日期：——
• Colautti,A. et al., Chimica Therapeutica, 1971, vol. 6, p. 367 - 379
  作者：Colautti,A. et al.

  DOI：——

  日期：——
• Mechanistic differences between in vitro assays for hydrazone-based small molecule inhibitors of anthrax lethal factor
  作者：M. Leslie Hanna、Theodore M. Tarasow、Julie Perkins

  DOI：10.1016/j.bioorg.2006.07.004

  日期：2007.2

  A systematically generated series of hydrazones were analyzed as potential inhibitors of anthrax lethal factor. The hydrazones were screened using one UV-based and two fluorescence-based in vitro assays. The study identified several inhibitors with IC50 values in the micromolar range, and importantly, significant differences in the types of inhibition were observed with the different assays. (c) 2006 Elsevier Inc. All rights reserved.
• Microwave Assisted Synthesis and Evaluation of N-Cinnamoyl Aryl Hydrazones for Cytotoxic and Antioxidant Activities
  作者：T.Sarala Devi

  DOI：10.13005/ojc/320350

  日期：2016.6.28

  A series of N-cinnamoyl aryl hydrazones 2a-2i were synthesized in good yields by microwave irradiation technique. The title compounds were formed by nucleophilic condensation of various N-1-substituted benzylidene-2-cyano aceto hydrazides with N,N-dimethyl amino benzaldehyde. The intermediate N-1-substituted benzylidene-2-cyano aceto hydrazide was obtained by condensing various substituted benzaldehydes with cyanoacetohydrazide. The structures of the compounds were characterized by IR, H-1 NMR and Mass spectra. The antioxidant activity was studied by reduction of DPPH, scavenging of nitric oxide and hydrogen peroxide methods with ascorbic acid as the standard drug. The compounds were evaluated for cytotoxic activity by BSLT method and their ED50 values were compared the standard podophyllotoxin. Among the compounds evaluated, N-1-benzylidene-2-cyano-3-(4-dimethylamino) phenyl acrylo hydrazide (2a) and N-1-(4-methoxy-benzylidene)-2-cyano3-(4-dimethylamino) phenyl acrylohydrazide (2e) showed good antioxidant activity towards all the three models. The compounds 2a and 2e showed ED50 values 3.07 mu g/ml and 3.7 mu g/ml respectively which were compared against the standard podophyllotoxin (1.64 mu g/ml).