N-(4-methoxyphenyl)-3-nitro-propanamide | 51833-87-5

• 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: N-(4-methoxyphenyl)-3-nitro-propanamide
• 英文别名: N-(4-methoxyphenyl)-3-nitropropanamide
• CAS: 51833-87-5
• 化学式: C₁₀H₁₂N₂O₄
• 分子量: 224.216
• InChiKey: LHIXOMXLHYTJLT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  84.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-硝基丙酸 、 甲氧苯胺 在 N,N'-二环己基碳二亚胺 作用下， 以65%的产率得到N-(4-methoxyphenyl)-3-nitro-propanamide
  参考文献：
  名称：

  Synthesis of various 3-nitropropionamides as Mycobacterium tuberculosis isocitrate lyase inhibitor

  摘要：

  Various 3-nitropropionamides were synthesized and evaluated for in vitro activities against log and starved phase culture of two mycobacterial species and Mycobacterium tuberculosis (MTB) isocitrate lyase (ICL) enzyme inhibition studies. Among 22 compounds, 1-cyclopropyl-7-(3,5-dimethyl-4-(3-nitropropanoyl) piperazin-1-yl)-6-fluoro-8-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (22) was found to be the most active compound in vitro with MICs of 0.16 and 0.04 mu M against log-and starved-phase culture of MTB. Compound 22 also showed good enzyme inhibition of MTB ICL with IC50 of 0.10 +/- 0.01 mu M. The docking studies also confirmed the binding potential of the compounds at the ICL active site. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.07.062

文献信息

• Verfahren zur Herstellung von reinen Nitro-aminobenzol-Verbindungen
  申请人：HOECHST AKTIENGESELLSCHAFT

  公开号：EP0292911A2

  公开（公告）日：1988-11-30

  Nitro-aminobenzol-Verbindungen, die durch übliche Nitrierung einer an der Aminogruppe mit einer Schutzgruppe versehenen Aminobenzol-Verbindung erhältlich sind, werden rein hergestellt, indem man die aminogruppengeschützte Nitro-aminobenzol-Verbindung zunächst isoliert, die Schutzgruppe mittels Schwefelsäure abspaltet, sodann das aus der Hydrolyse erhaltene Sulfatsalz der Nitro-­aminobenzol-Verbindung in Form des reinen, kristallinen Sulfates aus der Reaktionsmischung abscheidet und isoliert und hieraus gewünschtenfalls die freie Nitro-aminobenzol-­Verbindung in reiner Form gewinnt.

  通过对氨基上带有保护基团的氨基苯化合物进行常规硝化而得到的硝基氨基苯化合物的纯品制备方法是：首先分离出氨基上带有保护基团的硝基氨基苯化合物、用硫酸分离保护基团，然后从反应混合物中分离并分离出水解得到的纯结晶硫酸盐形式的硝基氨基苯化合物的硫酸盐，如果需要，还可以从中回收纯游离的硝基氨基苯化合物。
• Synthesis of various 3-nitropropionamides as Mycobacterium tuberculosis isocitrate lyase inhibitor
  作者：Dharmarajan Sriram、Perumal Yogeeswari、Swetha Methuku、Devambatla Ravi Kumar Vyas、Palaniappan Senthilkumar、Mallika Alvala、Variam Ullas Jeankumar

  DOI：10.1016/j.bmcl.2011.07.062

  日期：2011.9

  Various 3-nitropropionamides were synthesized and evaluated for in vitro activities against log and starved phase culture of two mycobacterial species and Mycobacterium tuberculosis (MTB) isocitrate lyase (ICL) enzyme inhibition studies. Among 22 compounds, 1-cyclopropyl-7-(3,5-dimethyl-4-(3-nitropropanoyl) piperazin-1-yl)-6-fluoro-8-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (22) was found to be the most active compound in vitro with MICs of 0.16 and 0.04 mu M against log-and starved-phase culture of MTB. Compound 22 also showed good enzyme inhibition of MTB ICL with IC50 of 0.10 +/- 0.01 mu M. The docking studies also confirmed the binding potential of the compounds at the ICL active site. (C) 2011 Elsevier Ltd. All rights reserved.