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Short Note

Synthesis of 2-methoxy-6-(pyrazin-2-ylimino methyl) phenol and its antibacterial activitity

by
A. A. Jarrahpour
1,*,
M. Motamedifar
2,
N. Hadi
2 and
M. Zarei
1
1
Department of Chemistry, College of Sciences, Shiraz University, Shiraz 71454, Iran
2
Department of Bacteriology & Virology , Shiraz Medical School , Shiraz University Medical Science , Shiraz 71345, Iran
*
Author to whom correspondence should be addressed.
Molbank 2004, 2004(1), M373; https://doi.org/10.3390/M373
Submission received: 30 January 2004 / Accepted: 18 February 2004 / Published: 24 February 2004
Versions Notes

Pyrazines are found in such heated foods as bread, different meats, baked potatoes and coffee [1],which are formed from serine and thereonine [2]. Pyrazine compounds have shown antifungal [3], antimyco- bacterial [3,4] activities. Furthermore, pyrazine derivatives have been used as antioxidation compounds [3,5,6]. Schiff bases have been used as ligands in complex formation with some metal ions [7]. They have shown biological activities including antibacterial [8,9,10], antifungal [9,10,11], anticancer [12,13] and herbicidal [14] activities. On the other hand, Schiff bases have applied as starting materials in the synthesis of a large bioactive and industrial compounds via ring closure, cycloaddition, replacement reactions, etc [15]. In addition, the methoxy group on the molecule enhances the various biological activities [16]. According to above facts, we synthesized 2-methoxy-6-(pyrazin-2-ylimino methyl) phenol 3 and then it was tested against four microorganisms Staphylococcus aureus (Gram positive), Bacillus subtilis (Gram positive), Kelebsiella pneumonia (Gram negative) and Pseudomonas aeruginosa (Gram negative). Compound 3 was moderately active against Kelebsiella pneumonia at 200 μg and it was inactive against other mentioned bacteria.
Molbank 2004 m373 i001
A mixture of 2-amino pyrazine 1 (0.95 g, 10.00 mmol), o-vanillin (2-hydroxy-3-methoxy benzaldehyde) 2 (1.52 g, 10.00 mmol) and anhydrous sodium sulfate (3.00 g) in dry dichloromethane (40.00 mL) was stirred at room temperature for five hours. The suspension was filtered and washed with CH2Cl2.The solvent was evaporated under reduced pressure and imine 3 was formed as a red solid which was recrystalized from methanol (1.90 g , 83%).
m.p.132-134 oC.
IR (KBr) (cm-1): 1575.73 (CH=N ), 1610.45 (C=N ring), 3190.5 -3645.20 (OH).
1H-NMR(CDCl3) (250 MHz)δ(ppm): 3.87 (3H, s, OCH3), 6.81-7.20 (3H, m, aryl hydrogens), 8.3-8.6 (3H, m, pyrazin ring), 9.3 (1H, s, N=CH), 13.30 (1H, br, OH).
13C- NMR (CDCl3) (62.90 MHz)δ(ppm): 56.64 (OCH3), 116.47-142.90 (aryl and pyrazine carbons), 167.30 (N=CH).
MS (m/z, %): 229 (M+, 60.3), 150 (HOPhOCH3CH=N, 22.0), 135 (HOPhOCH3C, 18.0), 106 (C4N2H3 N=C, 14.0), 79.0 (C4N2H3, 44.4), 43 (C-OCH3, 100.0), 41 (N=CH-N, 96.0).

Supplementary materials

Supplementary File 1Supplementary File 2Supplementary File 3

Acknowledgment

The authors thank the Shiraz University Research Council for financial support (Grant No. 81-SC-1540-C220).

References

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MDPI and ACS Style

Jarrahpour, A.A.; Motamedifar, M.; Hadi, N.; Zarei, M. Synthesis of 2-methoxy-6-(pyrazin-2-ylimino methyl) phenol and its antibacterial activitity. Molbank 2004, 2004, M373. https://doi.org/10.3390/M373

AMA Style

Jarrahpour AA, Motamedifar M, Hadi N, Zarei M. Synthesis of 2-methoxy-6-(pyrazin-2-ylimino methyl) phenol and its antibacterial activitity. Molbank. 2004; 2004(1):M373. https://doi.org/10.3390/M373

Chicago/Turabian Style

Jarrahpour, A. A., M. Motamedifar, N. Hadi, and M. Zarei. 2004. "Synthesis of 2-methoxy-6-(pyrazin-2-ylimino methyl) phenol and its antibacterial activitity" Molbank 2004, no. 1: M373. https://doi.org/10.3390/M373

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