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Benzimidazole-1,2,3-triazole hybrid molecules: synthesis and evaluation for antibacterial/antifungal activity.

Ouahrouch A, Ighachane H, Taourirte M, Engels JW, Sedra MH, Lazrek HB - Arch. Pharm. (Weinheim) (2014)

Bottom Line: A novel series of hybrid molecules 4a-i and 5a-i were prepared by condensation of 4-(trimethylsilylethynyl)benzaldehyde 1 with substituted o-phenylenediamines.These in turn were reacted with 2-(azidomethoxy)ethyl acetate in a Cu alkyne-azide cycloaddition (CuAAC) to generate the 1,2,3-triazole pharmacophore under microwave assistance.The newly synthesized compounds were examined for their in vitro antimicrobial activities against Gram-positive and Gram-negative bacteria and the phytopathogenic fungi Verticillium dahliae and Fusarium oxysporum f. sp. albedinis. 2-((4-(4-(5-Trifluoromethyl benzimidazol-2-yl)phenyl)-1,2,3-triazol-1-yl)methoxy)ethanol 5e showed a moderate inhibition of 30% in the Foa sporulation test.

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Affiliation: Laboratory of Bioorganic and Macromolecular Chemistry, Department of Chemistry, Faculty of Sciences and Technology Gueliz (FSTG), Marrakesh, Morocco; Laboratory of Biomolecular and Medicinal Chemistry, Department of Chemistry, Faculty of Sciences Semlalia, Marrakesh, Morocco; Institute for Organic Chemistry and Chemical Biology, Goethe-University Frankfurt am Main, Frankfurt am Main, Germany.

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X-ray crystal structure of compound 5a; displacement ellipsoids are drawn at the 50% probability level.
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fig01: X-ray crystal structure of compound 5a; displacement ellipsoids are drawn at the 50% probability level.

Mentions: The structures of all compounds were characterized by 1H NMR, 13C NMR, mass spectrometry, and HRMS spectra. The structure of 5a was also confirmed by X-ray diffraction analysis. This structure contains three planar parts: the benzimidazole, the benzene, and the triazole ring. Furthermore, various intermolecular hydrogen bond interactions between the molecules form a three-dimensional network (the hydrogen at N1 with the nitrogens at N4 and N5 as well as the hydrogen at O2 with the nitrogen at N2). The molecular structure of single crystal 5a is shown in Fig. 140.


Benzimidazole-1,2,3-triazole hybrid molecules: synthesis and evaluation for antibacterial/antifungal activity.

Ouahrouch A, Ighachane H, Taourirte M, Engels JW, Sedra MH, Lazrek HB - Arch. Pharm. (Weinheim) (2014)

X-ray crystal structure of compound 5a; displacement ellipsoids are drawn at the 50% probability level.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4225497&req=5

fig01: X-ray crystal structure of compound 5a; displacement ellipsoids are drawn at the 50% probability level.
Mentions: The structures of all compounds were characterized by 1H NMR, 13C NMR, mass spectrometry, and HRMS spectra. The structure of 5a was also confirmed by X-ray diffraction analysis. This structure contains three planar parts: the benzimidazole, the benzene, and the triazole ring. Furthermore, various intermolecular hydrogen bond interactions between the molecules form a three-dimensional network (the hydrogen at N1 with the nitrogens at N4 and N5 as well as the hydrogen at O2 with the nitrogen at N2). The molecular structure of single crystal 5a is shown in Fig. 140.

Bottom Line: A novel series of hybrid molecules 4a-i and 5a-i were prepared by condensation of 4-(trimethylsilylethynyl)benzaldehyde 1 with substituted o-phenylenediamines.These in turn were reacted with 2-(azidomethoxy)ethyl acetate in a Cu alkyne-azide cycloaddition (CuAAC) to generate the 1,2,3-triazole pharmacophore under microwave assistance.The newly synthesized compounds were examined for their in vitro antimicrobial activities against Gram-positive and Gram-negative bacteria and the phytopathogenic fungi Verticillium dahliae and Fusarium oxysporum f. sp. albedinis. 2-((4-(4-(5-Trifluoromethyl benzimidazol-2-yl)phenyl)-1,2,3-triazol-1-yl)methoxy)ethanol 5e showed a moderate inhibition of 30% in the Foa sporulation test.

View Article: PubMed Central - PubMed

Affiliation: Laboratory of Bioorganic and Macromolecular Chemistry, Department of Chemistry, Faculty of Sciences and Technology Gueliz (FSTG), Marrakesh, Morocco; Laboratory of Biomolecular and Medicinal Chemistry, Department of Chemistry, Faculty of Sciences Semlalia, Marrakesh, Morocco; Institute for Organic Chemistry and Chemical Biology, Goethe-University Frankfurt am Main, Frankfurt am Main, Germany.

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Related in: MedlinePlus