1-(2-硝基苯基)哌啶-2-羧酸 | 89860-65-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 中文名称: 1-(2-硝基苯基)哌啶-2-羧酸
• 英文名称: N-(2-nitrophenyl)-DL-pipecolic acid
• 英文别名: 1-(2-nitrophenyl) piperidine-2-carboxylic acid；1-(2-Nitrophenyl)piperidine-2-carboxylic acid
• CAS: 89860-65-1
• 化学式: C₁₂H₁₄N₂O₄
• mdl: MFCD08445182
• 分子量: 250.254
• InChiKey: DIIOPDWAPOGYKM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.416
• 拓扑面积：
  86.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(2-硝基苯基)哌啶-2-羧酸 在 palladium on activated charcoal 硫酸 、 potassium nitrate 作用下， 以 乙醇 、 环己烯 为溶剂， 反应 7.67h， 生成 7,8,9,10-tetrahydro-2-nitropyrido<1,2-a>quinoxalin-6-one
  参考文献：
  名称：

  Alo, Babajide I.; Avent, Anthony G.; Hanson, James R., Journal of the Chemical Society. Perkin transactions I, 1988, p. 1997 - 2000

  摘要：

  DOI：
• 作为产物：
  描述：

  1-氟-2-硝基苯 、 六氢吡啶-alpha-羧酸 在 碳酸氢钠 作用下， 以 乙醇 、 水 为溶剂， 以91%的产率得到1-(2-硝基苯基)哌啶-2-羧酸
  参考文献：
  名称：

  跨 C-3-N-4 键融合的三环和四环稠合喹喔啉-2-酮的合成

  摘要：

  我们研究了通过史蒂文斯重排螺-喹喔啉衍生的叶立德铵或用不同的还原剂处理 N-(2,4-二硝基苯基)-和 N-(2-硝基苯基) 亚胺酸来制备一些稠合喹喔啉酮。我们重新研究并澄清了一些从亚氨基酸衍生物开始的文献中发现的相关过程。还报道了稠合喹喔啉酮的其他反应，以及一些容易获得的 1-芳基二氢吲哚-2-羧酸到相应的 1-芳基吲哚的有用脱氢/脱羧反应。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)

  DOI：

  10.1002/ejoc.200300028

文献信息

• Synthesis of substituted N-(2′-nitrophenyl)pyrrolidine-2-carboxamides towards the design of proline-rich antimicrobial peptide mimics to eliminate bacterial resistance to antibiotics
  作者：Jocelyn A. Odusami、Monisola I. Ikhile、Josephat U. Izunobi、Idris A. Olasupo、Foluso O. Osunsanmi、Andrew R. Opoku、Marthe C.D. Fotsing、Olayinka T. Asekun、Oluwole B. Familoni、Derek T. Ndinteh

  DOI：10.1016/j.bioorg.2020.104340

  日期：2020.12

  The treatment of diseases is under threat due to the increasing resistance of disease-causing bacteria to antibiotics. Likewise, free radical-induced oxidative stress has been implicated in several human disease conditions, such as cancer, stroke and diabetes. In the search for amino acid analogues with antibacterial and antioxidant properties as possible mimics of antimicrobial peptides, substituted N-(2'-nitrophenyl)pyrrolidine-2-carboxamides 4a-4k and N-(2'-nitrophenyl)piperidine-2-carboxamides 4l-4n have been synthesized via a two-step, one-pot amidation of the corresponding acids, using thionyl chloride with different amines in dichloromethane. The carboxamides were characterized by infrared and nuclear magnetic resonance spectroscopy, mass spectrometry and elemental analysis. Carboxamides 4a-4n were assayed against five Gram-positive and five Gram-negative bacterial strains using the broth micro-dilution procedure and compared to standard antibiotic drugs (streptomycin and nalidixic acid). 4b showed the highest antibacterial activity with a minimum inhibitory concentration (MIC) value of 15.6 µg/mL against Staphylococcus aureus. Pertinently, 4b and 4k are promising candidates for narrow-spectrum (Gram-positive) and broad-spectrum antibiotics, respectively. The antioxidant properties of the carboxamides were also evaluated using the 1,1-diphenyl-2-picryl hydrazyl (DPPH) radical and 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulphonic acid) (ABTS) radical cation. 4a and 4k recorded the lowest IC₅₀ values of 1.22 × 10^-3 mg/mL (with DPPH) and 1.45 × 10^-4 mg/mL (with ABTS), respectively. Notably, 4k recorded about 2.5 times better antioxidant capacity than the positive controls - ascorbic acid and butylated hydroxyanisole. These results bode well for N-aryl carboxamides as good mimics and substitutes for antimicrobial peptides towards mitigating bacterial resistance to antibiotics as well as ameliorating oxidative stress-related diseases.
• Adegoke, E. A.; Alo, Babajide, Journal of Heterocyclic Chemistry, 1983, vol. 20, p. 1509 - 1512
  作者：Adegoke, E. A.、Alo, Babajide

  DOI：——

  日期：——
• ADEGOKE, E. A.;ALO, BABJIDE, J. HETEROCYCL. CHEM., 1983, 20, N 6, 1509-1512
  作者：ADEGOKE, E. A.、ALO, BABJIDE

  DOI：——

  日期：——