1-甲基-4-硝基-1H-吡咯-2-碳酰肼 | 28494-50-0

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 中文名称: 1-甲基-4-硝基-1H-吡咯-2-碳酰肼
• 英文名称: 1-methyl-4-nitropyrrole-2-carboxylic acid hydrazide
• 英文别名: 1-methyl-4-nitro-1H-pyrrole-2-carbohydrazide；1-methyl-4-nitro-pyrrole-2-carbohydrazide；1-Methyl-4-nitropyrrol-2-carbonsaeurehydrazid；1-methyl-4-nitropyrrole-2-carbohydrazide
• CAS: 28494-50-0
• 化学式: C₆H₈N₄O₃
• mdl: MFCD07843124
• 分子量: 184.155
• InChiKey: PKCOVLHJXVUBOX-UHFFFAOYSA-N

物化性质

• 密度：
  1.60±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.166
• 拓扑面积：
  106
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  1-甲基-4-硝基-1H-吡咯-2-碳酰肼 在 tetraphosphorus decasulfide 作用下， 以 xylene 为溶剂， 生成 1-methyl-2-(1,3,4-thiadiazol-2-yl)-4-nitropyrrole
  参考文献：
  名称：

  Shafiee, Abbas; Firoozi, Faranak; Javidnia, Katayoon, Phosphorus, Sulfur and Silicon and the Related Elements, 1994, vol. 96, # 1-4, p. 471 - 472

  摘要：

  DOI：
• 作为产物：
  描述：

  1-甲基-4-硝基-1H-吡咯-2-甲酸乙酯 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 0.25h， 以86%的产率得到1-甲基-4-硝基-1H-吡咯-2-碳酰肼
  参考文献：
  名称：

  取代的1-甲基-2-（1,3,4-噻二唑-2-基）-4-硝基吡咯和1-甲基-2-（1,3,4-恶二唑-2-基）-4-硝基吡咯的合成†

  摘要：

  从容易获得的4-硝基吡咯-2-羧酸乙酯（1），取代的1-甲基-2-（1,3,4-噻二唑-2-基）-4-硝基吡咯和1-甲基-2-（1制备了（3，4-恶二唑-2-基）-4-硝基吡咯。1与重氮甲烷的反应得到1-甲基-4-硝基吡咯-2-羧酸乙酯（2）。化合物2与水合肼反应，得到相应的酰肼3。的反应3与甲酸，得到1-（1-甲基-4-硝基-2-羧基）-2-（甲酰基）肼（7）。后者用五硫化二磷在二甲苯中回流，得到化合物6，产率为40％。化合物7的反应与五氧化二磷一起提供化合物9。在三乙胺存在下，化合物3与1,1'-羧基咪唑反应，生成2-（1-甲基-4-硝基-2-吡咯基）-1,3,4-恶二唑啉-4（H）-5-one（11）。将化合物3与溴化氰在甲醇中回流，得到化合物12。化合物13可通过化合物3与二硫化碳在碱性介质中反应获得。化合物13的烷基化得到相应的烷硫基衍生物14。1-甲基-4-硝基吡咯-2-羧酸的

  DOI：

  10.1002/jhet.5570320121

文献信息

• A novel class of oligomeric and polymeric d10 metal complexes of asymmetrical N-heterocyclic ligand with strong π-stacking and hydrogen bonding: syntheses, structures, and photoluminescence
  作者：Wang Jing-lin、Liu Bin、Yang Bin-sheng

  DOI：10.1039/c1ce05890h

  日期：——

  A novel asymmetric N-heterocyclic ligand, 1·H2O [1 = (E)-1-methyl-4-nitro-N′-(pyridin-2-ylmethylene)-1H-pyrrole-2-carbohydrazide], was generated by a facile route, and some closed shell metal complexes of the ligand were also synthesized. These complexes include [Zn(1)Cl2] (2), [Cd(1)(μ-Cl)2]n (3), [Hg(1)Cl2] (4) and [K(μ-1)(μ-NO3)]n (5), which were characterized by X-ray crystallography, IR and 1H-NMR spectroscopy, and elemental analyses. The structural studies indicate that ligand 1, with its different conformations and new coordination modes, is an important building block for designing and constructing supramolecular structures via π⋯π stacking, hydrogen bonding, Cl⋯Cl and d10–d10 interactions. These interactions not only reinforce the stability of structures, but also correlate with the physical properties of complexes. The UV and fluorescence spectral properties were investigated in solution. The titration experiments by d10 metal ions imply that ligand 1 forms stable complexes at a 1 : 1 ratio and exhibits enhanced fluorescence. Moreover, compared with the solution fluorescence spectra, the solid-state spectra show more significant red-shifts, suggesting that complexes 2–4 have possible applications as light emission materials.

  一种新型非对称N-杂环配体1·H2O [(E)-1-甲基-4-硝基-N'-(吡啶-2-亚甲基)-1H-吡咯-2-甲酰肼]通过简易方法合成，并合成了一系列闭壳层金属配合物。这些配合物包括[Zn(1)Cl2](2)、[Cd(1)(μ-Cl)2]n(3)、[Hg(1)Cl2](4)和[K(μ-1)(μ-NO3)]n(5)，并通过X射线晶体学、红外和核磁共振光谱以及元素分析进行了表征。结构研究表明，由于配体1具有不同的构象和新的配位模式，成为通过π…π堆积、氢键、Cl…Cl和d10-d10相互作用来设计构建超分子结构的重要构建块。这些相互作用不仅增强了结构的稳定性，而且与配合物的物理性质相关。此外，在溶液中研究了UV和荧光光谱性质。通过d10金属离子的滴定实验表明，配体1与金属离子以1:1比例形成稳定配合物并表现出增强的荧光。此外，与溶液荧光光谱相比，固态光谱显示出更显著的红移，表明配合物2-4有可能作为发光材料应用。
• 3-Aryl-6-aryl-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazines and analogs as activators of caspases and inducers of apoptosis and the use thereof
  申请人：Cai Xiong Sui

  公开号：US20080045514A1

  公开（公告）日：2008-02-21

  Disclosed are 3-aryl-6-aryl-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazines and analogs thereof, represented by the Formula I: wherein Ar 1 , Q 2 , R 1 , R 2 , dashed line and X are defined herein. The present invention relates to the discovery that compounds having Formula I are activators of caspases and inducers of apoptosis. Therefore, the activators of caspases and inducers of apoptosis of this invention may be used to induce cell death in a variety of clinical conditions in which uncontrolled growth and spread of abnormal cells occurs.

  本发明涉及一种由公式I表示的3-芳基-6-芳基-7H-[1,2,4]三唑并[3,4-b][1,3,4]噻二嗪及其类似物，其中Ar1，Q2，R1，R2，虚线和X的定义如下。本发明发现具有公式I的化合物是caspases的激活剂和凋亡诱导剂。因此，本发明的caspases激活剂和凋亡诱导剂可用于诱导在各种临床病况中出现的异常细胞的无控制增长和扩散的细胞死亡。
• Synthesis and evaluation of novel 4-nitropyrrole-based 1,3,4-oxadiazole derivatives as antimicrobial and anti-tubercular agents
  作者：Rajesh A. Rane、Pavankumar Bangalore、Sheetal D. Borhade、Preeti K. Khandare

  DOI：10.1016/j.ejmech.2013.09.039

  日期：2013.12

  We report synthesis and antimicrobial evaluation of 42 novel 4-nitropyrrole-based 1,3,4-oxadiazoles. The synthesized molecules were evaluated for anti-bacterial, anti-fungal and anti-tubercular activities. Promisingly, most of the compounds showed equal or more potency than standard ciprofloxacin against Staphylococcus aureus, Bacillus subtilis and Escherichia coll. Compound 5e exhibited highest antitubercular activity (0.46 mu g/mL) close to that of standard Isoniazid (0.40 mu g/mL). Equal antifungal activity (1.56 mu g/mL) compared to standard Amphotericin-B was shown by most of the compounds. All the N-methylated compounds showed more potent to equal activity against MSSA (MIC 0.39-1.56 mu g/mL) and MRSA (MIC 0.78-1.56 mu g/mL). All compounds were tested for mammalian cell toxicity using VERO cell line and were found to be non-toxic. (C) 2013 Elsevier Masson SAS. All rights reserved.
• Synthesis of novel 4-nitropyrrole-based semicarbazide and thiosemicarbazide hybrids with antimicrobial and anti-tubercular activity
  作者：Rajesh A. Rane、Shital S. Naphade、Pavan Kumar Bangalore、Mahesh B. Palkar、Mahamadhanif S. Shaikh、Rajshekhar Karpoormath

  DOI：10.1016/j.bmcl.2014.05.018

  日期：2014.7

  We report the synthesis and screening of forty novel 4-nitropyrrole-semicarbazide conjugates inspired from the reported bio-potential of bromopyrrole alkaloids and semicarbazide derivatives for antimicrobial activity. Herein, hybrids 5k-5o, 5r, 5s and 5t displayed four-fold increased activity (MIC = 0.39 mu g/mL) against Escherichia coli compared to standard ciprofloxacin. Eight hybrids, 5k-5o and 5r-5t displayed equal antibacterial activity (MIC = 1.56 mu g/mL) against Klebsiella pneumonia compared to standard ciprofloxacin. Hybrid, 5k-5o (MIC = 0.195 mu g/mL) displayed highly potent antibacterial activity against MSSA as compared to standard ciprofloxacin. Eight-fold superior activity was observed for four hybrids 5k-5m and 5o (MIC = 0.391 mu g/mL) against MRSA. Further, nine hybrids displayed four-fold superior antifungal activity (MIC = 0.78 mu g/mL) compared to standard Amphotericin B. Encouraging MICs of these hybrids recognize them as promising leads for development of potential antimicrobial drugs. (C) 2014 Elsevier Ltd. All rights reserved.
• Transition metal complexes of asymmetrical aroyl-hydrazone ligand: Syntheses, structures, DNA binding and cleavage studies
  作者：Wang Jing-lin、Zhao Ya-qin、Yang Bin-sheng

  DOI：10.1016/j.ica.2013.09.001

  日期：2014.1

  Syntheses and crystal structures of aroyl-hydrazone ligands and their transition metal complexes (E)-N'-(2-hydroxybenzylidene)-1-methyl-4-nitro-1H-pyrrole-2-carbohydrazide (H(2)1), [Cu-II(H1)Cl] (2), [Fe-III(H1) Cl-2(MeOH)] (3), [Mn-III(1)(mu-OMe)(MeOH)](2) (4), [(VO)-O-V(1)(OMe)] (5), Et3NH[(VO2)-O-V(1)] (6), [Co-II(H1)(mu-Cl)(H2O)](2) (7) and [Co-II(1)(2)] (7') are reported in this paper. The binding abilities of the compounds with calf thymus DNA are measured by using UV-Vis and fluorescence spectra. The apparent binding constant (K-obs = (1.66 +/- 0.21) x 10(4) M (1)) and rate constant (k(obs) = 3.62 +/- 0.17 h (1)) of 2 with CT-DNA is calculated, respectively. The quenching constants (K-q) 3.52 x 10(4) for 3, 1.97 x 10(4) for 4, 5.94 x 10(3) for 2, 3.32 x 10(3) for 7, 1.64 x 10(3) for 5, 1.55 x 10(3) M (1) for H(2)1 are determined, respectively, using ethidium bromide, as fluorescence probe. Agarose gel electrophoresis studies indicated that the complexes cleave plasmid pBR322 DNA by a hydrolytic mechanism. (C) 2013 Elsevier B.V. All rights reserved.