3-hydrazinyl-N-(4-nitrophenyl)-3-oxo-propanamide | 121222-79-5

• 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-hydrazinyl-N-(4-nitrophenyl)-3-oxo-propanamide
• 英文别名: 3-hydrazino-N-(4-nitrophenyl)-3-oxo-propanamide；3-hydrazinyl-N-(4-nitrophenyl)-3-oxopropanamide
• CAS: 121222-79-5
• 化学式: C₉H₁₀N₄O₄
• 分子量: 238.203
• InChiKey: VFFJIROOAWEDNS-UHFFFAOYSA-N

物化性质

• 沸点：
  624.5±40.0 °C(Predicted)
• 密度：
  1.484±0.06 g/cm3(Predicted)

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：
  0.11
• 拓扑面积：
  130
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-hydrazinyl-N-(4-nitrophenyl)-3-oxo-propanamide 在 三乙胺 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 2.0h， 生成 Propanediamide, N-[(2R,3S)-2-[4-(acetyloxy)-3-methoxyphenyl]-3-chloro-4-oxo-1-azetidinyl]-N'-(4-nitrophenyl)-
  参考文献：
  名称：

  N/C-4 substituted azetidin-2-ones: Synthesis and preliminary evaluation as new class of antimicrobial agents

  摘要：

  A series of 3-chloro-4-(3-methoxy-4-acetyloxyphenyl)-1-[3-oxo-3-(phenylamino)propanamido] azetidin-2-ones 3a-g and 3-chloro-4-[2-hydroxy-5-(nitro substituted phenylazo)phenyll-1-phenylazetidin-2-ones 6a-h were synthesized using appropriate synthetic route. Structures of all the synthesized compounds were established on the basis of elemental analysis and spectroscopic data. The antimicrobial activity of the synthesized compounds was screened against several microbes. Several of these molecules showed potent antimicrobial activity against Bacillus anthracis, Staphyococcus aureus and Candida albicans and significant structure-activity relationship (SAR) trends. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.10.064
• 作为产物：
  描述：

  3-(4-硝基苯胺基)-3-氧代丙酸乙酯 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 1.0h， 生成 3-hydrazinyl-N-(4-nitrophenyl)-3-oxo-propanamide
  参考文献：
  名称：

  Bhatt; Dave; Undavia, Journal of the Indian Chemical Society, 1988, vol. 65, # 11, p. 799 - 800

  摘要：

  DOI：

文献信息

• Bhatt; Dave; Undavia, Journal of the Indian Chemical Society, 1988, vol. 65, # 11, p. 799 - 800
  作者：Bhatt、Dave、Undavia、Trivedi

  DOI：——

  日期：——
• Trivedi, P. B.; Undavia, N. K.; Dave, A. M., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1993, vol. 32, # 7, p. 760 - 765
  作者：Trivedi, P. B.、Undavia, N. K.、Dave, A. M.、Bhatt, K. N.、Desai, N. C.

  DOI：——

  日期：——
• Halve, Anand K.; Dubey, Rakesh; Bhadauria, Deepti, Journal of the Indian Chemical Society, 2006, vol. 83, # 4, p. 386 - 388
  作者：Halve, Anand K.、Dubey, Rakesh、Bhadauria, Deepti、Bhaskar, Bhuwan、Gour, Poonam

  DOI：——

  日期：——
• BHATT, K. N.;DAVE, A. M.;UNDAVIA, N. K.;TRIVEDI, P. B., J. INDIAN CHEM. SOC., 65,(1988) N 11, C. 799-800
  作者：BHATT, K. N.、DAVE, A. M.、UNDAVIA, N. K.、TRIVEDI, P. B.

  DOI：——

  日期：——
• Design, synthesis and molecular docking of substituted 3-hydrazinyl-3-oxo-propanamides as anti-tubercular agents
  作者：Arshi Naqvi、Richa Malasoni、Akansha Srivastava、Rishi Ranjan Pandey、Anil Kumar Dwivedi

  DOI：10.1016/j.bmcl.2014.09.080

  日期：2014.11

  Based on the anti-mycobacterial activity of various acid hydrazides, a series of substituted 3-hydrazinyl-3-oxo-propanamides has been designed. The target compounds have been synthesized from diethylmalonate using substituted amines and hydrazine hydrate in ethanol. Computational studies and anti-tubercular activity screenings were undertaken to test their inhibitory effect on protein kinase PknB from Mycobacterium tuberculosis. Binding poses of the compounds were energetically favorable and showed good interactions with active site residues. Designed molecules obey the Lipinski's rule of 5 and gave moderate to good drug likeness score. Among the sixteen compounds (1-16) taken for in silico and in vitro studies, 3 compounds (11, 12 and 15) have shown good binding energies along with exhibiting good anti-tubercular activity and thus may be considered as a good inhibitors of PknB. (C) 2014 Elsevier Ltd. All rights reserved.