3-(2-硝基苯胺基)-3-氧代丙酸乙酯 | 91088-48-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3-(2-硝基苯胺基)-3-氧代丙酸乙酯
• 英文名称: N-(2-nitrophenyl)malonamic acid ethyl ester
• 英文别名: ethyl 2'-nitromalonanilate；C-<2-Nitro-phenylcarbamoyl>-essigsaeure-aethylester；C-(2-Nitro-phenylcarbamoyl)-essigsaeure-aethylester；Ethyl 3-(2-nitroanilino)-3-oxopropanoate
• CAS: 91088-48-1
• 化学式: C₁₁H₁₂N₂O₅
• 分子量: 252.227
• InChiKey: BXIINKFGAIBTLJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(2-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 5.0h， 生成 3-hydrazinyl-N-(2-nitrophenyl)-3-oxo-propanamide
  参考文献：
  名称：

  Design, synthesis and molecular docking of substituted 3-hydrazinyl-3-oxo-propanamides as anti-tubercular agents

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2014.09.080
• 作为产物：
  描述：

  2-硝基苯胺 、 氯甲酰乙酸乙酯 在 三乙胺 作用下， 以 丙酮 为溶剂， 反应 4.0h， 生成 3-(2-硝基苯胺基)-3-氧代丙酸乙酯
  参考文献：
  名称：

  Ethyl malonate amides: A diketo acid offspring fragment for HIV integrase inhibition

  摘要：

  While searching for new HIV integrase inhibitors we discovered that some ethyl malonate amides (EMA) are active against this enzyme. Surprisingly, the main function can only very rarely be found among the reported drug candidates. We synthesised a series of compounds in order to establish and analyse the structure-activity relationship. The similarity to the important classes of HIV integrase inhibitors as well as the synthetic availability of the different targets including this pharmacophore makes EMA compounds an interesting object of investigations. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.06.054

文献信息

• Synthesis of substituted 1,2-dihydropyridines by reaction of ethyl N-arylmalonamates with ethyl 2-(ethoxymethylidene)-3-oxobutanoate
  作者：S. S. Hayotsyan、A. H. Hasratyan、A. A. Sargsyan、A. Kh. Khachatryan、A. E. Badasyan、S. G. Kon’kova、M. S. Sargsyan

  DOI：10.1134/s1070428016060166

  日期：2016.6

  Michael addition of ethyl N-arylmalonamates to ethyl 2-(ethoxymethylidene)-3-oxobutanoate in ethanol in the presence of triethylamine at room temperature afforded the corresponding adducts which underwent cyclization to diethyl 1-aryl-6-methyl-2-oxo-1,2-dihydropyridine-3,5-dicarboxylates in 17–65% yield. N-Alkylmalonamic acid esters failed to react with ethyl 2-(ethoxymethylidene)-3-oxobutanoate under

  在室温下在三乙胺存在下，在乙醇中将N-芳基丙二酸乙酯的迈克尔加成至2-（乙氧基亚甲基）-3-氧代丁酸乙酯中，得到相应的加合物，将其环合成1-乙基-6-芳基-2-甲基-2-氧代-1 ，2-二氢吡啶-3,5-二羧酸酯的产率为17-65％。在类似条件下，N-烷基丙二酸酯不能与2-（乙氧基亚甲基）-3-氧代丁酸乙酯反应。
• Synthesis and Characterization of <i>N</i>-Acylaniline Derivatives as Potential Chemical Hybridizing Agents (CHAs) for Wheat (<i>Triticum aestivum</i> L.)
  作者：Kajal Chakraborty、C. Devakumar

  DOI：10.1021/jf061390x

  日期：2006.9.1

  generally furnished analogues like 4'-fluoroacetoacetanilide (7) and ethyl 4'-fluoromalonanilate (1), which induced 89.12 and 84.66% male sterility, respectively, in PBW 343. Among halogenated acetanilides, the increasing number of chlorine atoms in the side chain led to an increase in the activity of 4'-fluoro (23) and 4'-bromo (24) derivatives of trichoroacetanilides, which induced >87% male sterility. Quantitative

  通过部署化学杂交剂（CHA）诱导雄性不育在自花授粉作物（如小麦）的杂种育种中很重要，其中雄性和雌性器官都在同一朵花中。在较早的水稻研究工作的牵头下，合成了总共25种由丙二酸，乙酰乙酰苯胺和乙酰苯胺（包括卤代乙酰苯胺）组成的N-酰基苯胺，并将其筛选为三种小麦基因型的CHAs，即PBW 343，HD 2046。 ，以及2001-2002年冬季的1500 ppm HD 2733。通过将取代的苯胺与适当的二酯，酰氯或单酯缩合来合成在酰基和芳族结构域上具有变化的N-丙氨酸。经鉴定，在芳基环对位具有高电负性基团（例如F / Br）的测试化合物是最有效的CHAs，可引起更高的雄性不育性。N取代在侧链上的变化通常提供类似物，如4'-氟乙酰乙酰苯胺（7）和4'-氟丙二酸乙基苯酯（1），它们分别在PBW 343中引起89.12和84.66％的雄性不育。侧链中氯原子数目的增加导致三氯乙酰苯胺的4'-氟（23）和
• 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：——
• Synthesis of substituted dihydropyridines by reacting ethoxymethylidenemalonate with malonic acid N-arylamidoesters
  作者：S. S. Hayotsyan、S. G. Kon’kova、A. G. Hasratyan、A. Kh. Khachatryan、A. E. Badasyan、A. A. Sargsyan、G. A. Panosyan、M. S. Sargsyan

  DOI：10.1134/s1070363216100145

  日期：2016.10

  Reactions of ethoxymethylidenemalonate with malonic acid N-arylamidoesters in the presence of triethylamine afforded diethyl 1-aryl-6-hydroxy-2-oxo-1,2-dihydropyridine-3,5-dicarboxylates via the cyclization of Michael adducts. In the presence of sodium ethoxide the formed adducts may be also involved into simultaneous retro-Michael reaction leading to the formation of ethyl 1-aryl-5-arylcarbamoyl-6-hydroxy-2-oxo-1,2-dihydropyridine-3-carboxylates. Direction of heterocyclization or retro-Michael reaction is determined by the acidity of the hydrogen atoms of adducts and basicity of catalyst.
• 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：——