N'-(benzenesulfonamido)pyrazine-2-carboximidamide | 883051-25-0

• 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: N'-(benzenesulfonamido)pyrazine-2-carboximidamide
• CAS: 883051-25-0
• 化学式: C₁₁H₁₁N₅O₂S
• 分子量: 277.307
• InChiKey: XRTXEDXBZCAGKN-UHFFFAOYSA-N

物化性质

• 熔点：
  205 °C(Solv: methanol (67-56-1))
• 沸点：
  450.8±48.0 °C(Predicted)
• 密度：
  1.46±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  119
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N'-(benzenesulfonamido)pyrazine-2-carboximidamide 、 草酰氯 在 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 以81%的产率得到N-(4,5-dioxo-2-(pyrazin-2-yl)-4,5-dihydroimidazol-1-yl)benzenesulfonamide
  参考文献：
  名称：

  Synthesis of biologically active N-methyl derivatives of amidines and cyclized five-membered products of amidines with oxalyl chloride

  摘要：

  A series of substituted N-methylisonicotinamidine (2a-f), N-methylpyrazine-2-carboxamidine (2g-i) derivatives were synthesized by reaction of amidine derivatives (1a-i) with methyl iodide in presence of triethylamine. Five-membered condensed dihydroimidazolylbenzene-sulfonamide derivatives (3a-i) were obtained by the reaction of amidine derivatives (1a-i) with acylating agent oxalyl chloride. All the compounds, i.e. 2a-i and 3a-i were purified by crystallization. Structures of all the synthesized compounds are supported by correct IR, H-1 NMR, mass spectral and analytical data. Anti-inflammatory activity evaluation was carried out using carrageenan-induced paw oedema assay and compounds 2e, 3a and 3d exhibited good anti-inflammatory activity (44%, 31% and 37% activity at 50 mg/kg p.o., respectively). Analgesic activity evaluation was carried out using acetic acid writhing assay and compounds 2a and 3f gave 75% activity each at 100 mg/kg p.o.; on the other hand compounds 3a and 3d exhibited 60% analgesic activity each at 50 mg/kg p.o. Compounds 3a and 3d exhibited good anti-inflammatory and analgesic activities. (C) 2007 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2007.10.005
• 作为产物：
  描述：

  2-氰基吡嗪 以 甲醇 为溶剂， 反应 8.0h， 生成 N'-(benzenesulfonamido)pyrazine-2-carboximidamide
  参考文献：
  名称：

  某些am和衍生物的合成，抗炎和镇痛活性评估。

  摘要：

  在甲醇钠存在下，氰基吡啶和氰基吡嗪与磺酰肼缩合，合成了许多am衍生物（3a-i）。通过固相微波辐射，将2-乙酰基吡啶和4-乙酰基吡啶与磺酰肼缩合，得到相应的（5a-d）。通过在乙酸中回流，将3-吲哚甲醛与磺酰肼缩合，得到相应的缩合产物（5e和f）。通过结晶或通过柱色谱法纯化所有化合物，即3a-i和5a-f。正确的IR，（1）H NMR，质谱和分析数据支持所有合成化合物的结构。使用角叉菜胶诱导的爪水肿测定法进行抗炎活性评估，化合物3e，f和5e表现出良好的抗炎活性，口服50 mg / kg时分别为52％，37％和38％。使用乙酸扭曲试验进行镇痛活性评估，化合物3a，c，e和5f表现出良好的镇痛活性，即在50 mg / kg po下分别具有50％，50％，50％和60％的镇痛活性。

  DOI：

  10.1016/j.bmc.2006.02.014

文献信息

• Studies on pyrazine derivatives LII: Antibacterial and antifungal activity of nitrogen heterocyclic compounds obtained by pyrazinamidrazone usage
  作者：Henryk Foks、Lukasz Balewski、Katarzyna Gobis、Maria Dabrowska-Szponar、Katarzyna Wisniewska

  DOI：10.1002/hc.20751

  日期：——

  orthoformate and orthoacetate or benzoyl chloride. N′-Phenylamidrazones 3, 8 in reaction with thionyl chloride were transformed to 1,2,3,5-thiatriazole S-oxides 39, 40. Obtained compounds exhibited low antibacterial activity. Antifungal activity was affirmed for compounds 1, 3, 4, 5, 8, 37, 39, and 40, for which minimal inhibitory concentration (MIC) was in the concentration range of 16–128 μg/mL.

  利用吡嗪脒及其 N'-取代衍生物 1-8 的反应性与磺酰氯砜衍生物 9-17 反应，得到原甲酸酯环化成磺酰化合物 18-20。腙与吡嗪亚氨基酯反应得到二酰肼 21-23，其环化为 1,2,4-三唑 24-26 的 3,5-二吡嗪衍生物。1-甲基-或1-苯基-3-吡嗪-1,2,4-三唑27-38在脒腙1-8与原甲酸酯和原乙酸酯或苯甲酰氯的反应中形成。N'-Phenylamidrazones 3, 8 与亚硫酰氯反应转化为 1,2,3,5-噻三唑 S-氧化物 39, 40。获得的化合物表现出低抗菌活性。化合物 1、3、4、5、8、37、39 和 40 的抗真菌活性得到确认，其最小抑制浓度 (MIC) 的浓度范围为 16–128 μg/mL。© 2011 Wiley Periodicals, Inc. 杂原子化学 23:49–58, 2012; 在 wileyonlinelibrary.com 上在线查看这篇文章。DOI
• 10.1016/j.tet.2024.134066
  作者：Alizadeh, Vali、Garcia-Santos, Isabel、Castiñeiras, Alfonso、Mahmoudi, Ghodrat、Safin, Damir A.

  DOI：10.1016/j.tet.2024.134066

  日期：——

  higher in comparison to the previously reported synthesis using pyrazine-2-carbohydrazonamide and benzenesulfonyl chloride. Molecules of the title compound are linked via N–H⋯O, C–H⋯Ph, S=O⋯2-pyrazine and π⋯π interactions. As it was found by the Hirshfeld surface analysis, molecules of interact through H⋯X (X = H, C, N and O) contacts. Electronic properties of were revealed using the Density Functional

  报道了通过物理测量和计算工具研究的吡嗪酰胺-苯磺酰肼杂化物-(苯磺酰基)吡嗪-2-碳酰肼()。该化合物是利用金属钠辅助 2-氰基吡嗪与苯磺酰肼在无水甲醇中相互作用来合成的。我们新开发的合成方法能够以 74% 的产率获得标题化合物，这比之前报道的使用吡嗪-2-碳腙酰胺和苯磺酰氯的合成方法高出两倍多。标题化合物的分子通过 N–H⋯O、C–H⋯Ph、S=O⋯2-吡嗪和 π⋯π 相互作用连接。正如赫什菲尔德表面分析发现的那样，分子通过 H⋯X（X = H、C、N 和 O）接触相互作用。使用密度泛函理论（DFT）计算揭示了电子特性。预计为四级毒性，不能透过血脑屏障，但有可能被胃肠道吸收。据预测，该化合物对 PLpro、Nsp3_range 207-379 MES 和 Nsp16_SAM 位点表现出最强的活性，可抑制 SARS-CoV-2 蛋白的活性。尽管该值稍高，但复合物 PLpro– 的配体效率分数被发现是命中的特征。
• Synthesis, anti-inflammatory and analgesic activity evaluation of some amidine and hydrazone derivatives
  作者：Sham M. Sondhi、Monica Dinodia、Ashok Kumar

  DOI：10.1016/j.bmc.2006.02.014

  日期：2006.7

  spectral and analytical data. Anti-inflammatory activity evaluation was carried out using carrageenin-induced paw oedema assay and compounds 3e,f and 5e exhibited good anti-inflammatory activity, that is 52%, 37% and 38% at 50 mg/kg po, respectively. Analgesic activity evaluation was carried out using acetic acid writhing assay and compounds 3a,c,e and 5f showed good analgesic activity, that is, 50%, 50%

  在甲醇钠存在下，氰基吡啶和氰基吡嗪与磺酰肼缩合，合成了许多am衍生物（3a-i）。通过固相微波辐射，将2-乙酰基吡啶和4-乙酰基吡啶与磺酰肼缩合，得到相应的（5a-d）。通过在乙酸中回流，将3-吲哚甲醛与磺酰肼缩合，得到相应的缩合产物（5e和f）。通过结晶或通过柱色谱法纯化所有化合物，即3a-i和5a-f。正确的IR，（1）H NMR，质谱和分析数据支持所有合成化合物的结构。使用角叉菜胶诱导的爪水肿测定法进行抗炎活性评估，化合物3e，f和5e表现出良好的抗炎活性，口服50 mg / kg时分别为52％，37％和38％。使用乙酸扭曲试验进行镇痛活性评估，化合物3a，c，e和5f表现出良好的镇痛活性，即在50 mg / kg po下分别具有50％，50％，50％和60％的镇痛活性。
• Synthesis of biologically active N-methyl derivatives of amidines and cyclized five-membered products of amidines with oxalyl chloride
  作者：Sham M. Sondhi、Monica Dinodia、Shubhi Jain、Ashok Kumar

  DOI：10.1016/j.ejmech.2007.10.005

  日期：2008.12

  A series of substituted N-methylisonicotinamidine (2a-f), N-methylpyrazine-2-carboxamidine (2g-i) derivatives were synthesized by reaction of amidine derivatives (1a-i) with methyl iodide in presence of triethylamine. Five-membered condensed dihydroimidazolylbenzene-sulfonamide derivatives (3a-i) were obtained by the reaction of amidine derivatives (1a-i) with acylating agent oxalyl chloride. All the compounds, i.e. 2a-i and 3a-i were purified by crystallization. Structures of all the synthesized compounds are supported by correct IR, H-1 NMR, mass spectral and analytical data. Anti-inflammatory activity evaluation was carried out using carrageenan-induced paw oedema assay and compounds 2e, 3a and 3d exhibited good anti-inflammatory activity (44%, 31% and 37% activity at 50 mg/kg p.o., respectively). Analgesic activity evaluation was carried out using acetic acid writhing assay and compounds 2a and 3f gave 75% activity each at 100 mg/kg p.o.; on the other hand compounds 3a and 3d exhibited 60% analgesic activity each at 50 mg/kg p.o. Compounds 3a and 3d exhibited good anti-inflammatory and analgesic activities. (C) 2007 Elsevier Masson SAS. All rights reserved.