6-甲氧基吡嗪甲亚胺酸甲酯 | 59484-60-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 6-甲氧基吡嗪甲亚胺酸甲酯
• 英文名称: 6-methoxypyrazine-2-carbimidate
• 英文别名: 6-Methoxy-pyrazin-2-imidsaeure-methyl-ester；methyl 6-methoxypyrazine-2-carbimidate；6-methoxy-pyrazine-2-carboximidic acid methyl ester；Methyl 6-methoxypyrazine-2-carboximidate
• CAS: 59484-60-5
• 化学式: C₇H₉N₃O₂
• mdl: MFCD00233278
• 分子量: 167.167
• InChiKey: RCRTVSFDPQCCSK-UHFFFAOYSA-N

物化性质

• 熔点：
  100-101 °C
• 沸点：
  235.3±50.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.285
• 拓扑面积：
  68.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-甲氧基吡嗪甲亚胺酸甲酯 在 苯磺酰肼 作用下， 以 甲醇 、 水 为溶剂， 以28%的产率得到bis-(α-aminomethylene-6-methoxypyrazin-2-yl)hydrazine
  参考文献：
  名称：

  吡嗪衍生物LII的研究：使用吡嗪酰胺获得的含氮杂环化合物的抗菌和抗真菌活性

  摘要：

  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

  DOI：

  10.1002/hc.20751
• 作为产物：
  描述：

  甲醇 、 2-氰基-6-甲氧基哌嗪 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 反应 0.5h， 生成 6-甲氧基吡嗪甲亚胺酸甲酯
  参考文献：
  名称：

  Synthesis, structure, and antimicrobial activity of heterocyclic phenylsulfonyl- and 4-aminophenylsulfonyl-carboximidamides

  摘要：

  A series of novel phenylsulfonyl- and 4-aminophenylsulfonyl-carboximidamides were synthesized by condensation of sulfonamides with heterocyclic methyl carbimidates obtained from heterocyclic carbonitriles and used 'at its inception.' The molecular structure of the obtained compounds is discussed. Compounds possessing heterocyclic systems with a nitrogen atom in the alpha position to the functional group showed a different single-crystal structure than expected. The synthesized derivatives were evaluated for antimicrobial activities: tuberculostatic, antibacterial, and antifungal..

  DOI：

  10.1007/s00706-012-0769-6

文献信息

• Synthesis and Antimicrobial Activity of Novel Heterocyclic Sulfamoyl-phenyl-carboximidamides Derived from Clinically Applied Sulfonamides
  作者：Katarzyna Gobis、Henryk Foks、Katarzyna Wiśniewska、Maria Dąbrowska-Szponar、Ewa Augustynowicz-Kopeć、Agnieszka Napiórkowska

  DOI：10.1002/ardp.201200160

  日期：2012.11

  A series of novel heterocyclic sulfamoyl‐phenyl‐carboximidamides were synthesized in satisfactory yields via condensation of clinically applied sulfonamides with heterocyclic methyl carbimidates. New structures were confirmed by IR and NMR spectra as well as elemental analyses. All the compounds were screened for their antibacterial, antifungal, and tuberculostatic activities. Preliminary results indicated

  通过临床应用的磺酰胺与杂环甲基碳酰亚胺酯的缩合，合成了一系列新型杂环氨磺酰基-苯基-羧酰亚胺酰胺，收率令人满意。新结构通过 IR 和 NMR 光谱以及元素分析得到证实。筛选了所有化合物的抗菌、抗真菌和抗结核活性。初步结果表明，一些目标化合物表现出良好的抗菌效力。特别是，发现 N-[4-(噻唑-2-氨磺酰基)苯基]吡嗪-2-羧酰亚胺酰胺 (16) 与临床应用的磺胺甲氧哒嗪一样有效。
• Synthesis, structure, and biological activity of novel heterocyclic sulfonyl-carboximidamides
  作者：Katarzyna Gobis、Henryk Foks、Jarosław Sławiński、Artur Sikorski、Damian Trzybiński、Ewa Augustynowicz-Kopeć、Agnieszka Napiórkowska、Krzysztof Bojanowski

  DOI：10.1007/s00706-012-0888-0

  日期：2013.5

  A series of novel heterocyclic sulfonyl-carboximidamides were synthesized in satisfactory yields via condensation of heterocyclic methyl carbimidates with 2-chlorobenzenesulfonamide and 4-chloropyridine-3-sulfonamide. New structures were confirmed by IR and NMR spectra as well as elemental analyses. X-ray crystallography of two derivatives was performed. The single-crystal structures confirmed the presence of a primary amine group in the amidine moiety. All the compounds were screened for their tuberculostatic, antibacterial, and anticancer activities. Preliminary results indicated that target compounds exhibited weak tuberculostatic and antibacterial activities. Seven compounds inhibited the growth of some cancer cell lines, whereas one of the 2-quinoline derivatives displayed favorable activity against all tested cancer cells with GI (50) values of 0.92-13 mu M.
• Orlewska; Foks; Janowiec, Pharmazie, 1995, vol. 50, # 8, p. 565 - 566
  作者：Orlewska、Foks、Janowiec、Zwolskakwiek

  DOI：——

  日期：——
• FOKS, H.;JANOWIEC, M., ACTA POL. PHARM., 1982, 39, N 1-3, 79-82
  作者：FOKS, H.、JANOWIEC, M.

  DOI：——

  日期：——
• FOKS H.; PANCECHOWSKA D., ACTA POL. PHARM. <APPH-AX>, 1976, 33, NO 1, 49-54
  作者：FOKS H.、 PANCECHOWSKA D.

  DOI：——

  日期：——