(3-chloro-phenylhydrazono)-cyano-acetic acid ethyl ester | 36874-67-6

• 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: (3-chloro-phenylhydrazono)-cyano-acetic acid ethyl ester
• 英文别名: (3-Chlor-phenylhydrazono)-cyan-essigsaeure-aethylester；Ethyl 2-[(3-chlorophenyl)hydrazinylidene]-2-cyanoacetate
• CAS: 36874-67-6
• 化学式: C₁₁H₁₀ClN₃O₂
• 分子量: 251.672
• InChiKey: FSIFRTHCIGOKNH-UHFFFAOYSA-N

物化性质

• 熔点：
  91 °C
• 沸点：
  348.9±44.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  74.5
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 海关编码：
  2928000090

反应信息

• 作为反应物：
  描述：

  (3-chloro-phenylhydrazono)-cyano-acetic acid ethyl ester 在 氢氧化钾 作用下， 以 吡啶 为溶剂， 反应 9.0h， 生成 3-[3-Amino-4-(3-chloro-phenylazo)-2-(2-cyano-ethyl)-5-oxo-2,5-dihydro-pyrazol-1-yl]-propionitrile
  参考文献：
  名称：

  Elgemeie, Galal H.; Elghandour, Ahmed H.; Elshimy, Hamdy M., Journal fur praktische Chemie (Leipzig 1954), 1989, vol. 331, # 3, p. 466 - 474

  摘要：

  DOI：
• 作为产物：
  描述：

  氰乙酸乙酯 、 alkaline earth salt of/the/ methylsulfuric acid 在 sodium carbonate 作用下， 生成 (3-chloro-phenylhydrazono)-cyano-acetic acid ethyl ester
  参考文献：
  名称：

  五线谱; 尝试合成辛啉核。

  摘要：

  DOI：

  10.1021/jo01165a007

文献信息

• Phenyl hydrazone bearing pyrazole and pyrimidine scaffolds: design and discovery of a novel class of non-nucleoside reverse transcriptase inhibitors (NNRTIs) against HIV-1 and their antibacterial properties
  作者：Udaya Pratap Singh、Hans Raj Bhat、Amita Verma、Mukesh Kumar Kumawat、Rajinder Kaur、S. K. Gupta、Ramendra K. Singh

  DOI：10.1039/c3ra41604f

  日期：——

  A novel series of phenyl hydrazone bearing pyrazole and pyrimidine hybrid compounds has been designed using the molinspiration toolkit based on Lipinski's rule of five and developed via sequential reactions starting from the diazotization of different anilines and further active methylation with acetyl acetone, ethyl acetoacetate and ethyl cyanoacetate to generate hydrazono derivatives. The target hybrid compounds were synthesized on cyclisation of the resulting hydrazono derivatives with hydrazine, phenyl hydrazine and urea. These molecules have been subsequently tested for anti-HIV activity using TZM-bl cell lines. The MTT assay was also carried out for the cytotoxicity determination of the active compounds. Further, to exemplify the key structural features of the molecules, a molecular docking analysis of the most active compounds was performed at the NNIBP of the HIV-RT protein. The antibacterial activity of the target compounds was also determined against a panel of four Gram-positive and four Gram-negative human pathogens. All molecules showed a potent anti-HIV activity along with a prominent inhibition of bacterial organisms.

  一种新的系列含有吡唑和嘧啶杂合化合物的苯肼酮已被设计，这一设计基于Lipinski五条规则，并通过从不同苯胺的重氮化反应开始，随后与乙酰乙酸、乙基乙酰乙酸和乙基氰乙酸的活性甲基化反应生成肼酮衍生物。目标杂合化合物是在生成的肼酮衍生物与肼、苯肼和尿素环化反应后合成的。这些分子随后在TZM-bl细胞系中进行了抗HIV活性测试。此外，还进行了MTT法以确定活性化合物的细胞毒性。为了说明这些分子的关键结构特征，还对最活跃化合物在HIV-RT蛋白的NNIBP进行了分子对接分析。目标化合物的抗菌活性也针对四种革兰氏阳性菌和四种革兰氏阴性人类病原体进行了检测。所有分子均显示出强效的抗HIV活性以及显著的细菌抑制作用。
• Rymareva; Torgasheva; Zelikhover, Russian Journal of General Chemistry, 1997, vol. 67, # 9, p. 1417 - 1423
  作者：Rymareva、Torgasheva、Zelikhover、Bel'skii

  DOI：——

  日期：——
• Shawali, Ahmad S.; Albar, Hassan A., Canadian Journal of Chemistry, 1986, vol. 64, p. 871 - 875
  作者：Shawali, Ahmad S.、Albar, Hassan A.

  DOI：——

  日期：——
• Elgemeie, Galal H.; Elghandour, Ahmed H.; Elshimy, Hamdy M., Journal fur praktische Chemie (Leipzig 1954), 1989, vol. 331, # 3, p. 466 - 474
  作者：Elgemeie, Galal H.、Elghandour, Ahmed H.、Elshimy, Hamdy M.

  DOI：——

  日期：——
• CINNOLINES. III. ATTEMPTED SYNTHESES OF THE CINNOLINE NUCLEUS¹
  作者：NELSON J. LEONARD、SAMUEL N. BOYD、HARRY F. HERBRANDSON

  DOI：10.1021/jo01165a007

  日期：1947.1