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Molecules 2013, 18(10), 12645-12662; doi:10.3390/molecules181012645

Structural Studies and Investigation on the Activity of Imidazole-Derived Thiosemicarbazones and Hydrazones against Crop-Related Fungi

, , , , , ,  and *
Departamento de Química, Universidade Federal de Minas Gerais, Belo Horizonte 31270-901, MG, Brazil
* Author to whom correspondence should be addressed.
Received: 14 August 2013 / Revised: 25 September 2013 / Accepted: 26 September 2013 / Published: 14 October 2013
(This article belongs to the Section Medicinal Chemistry)
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New imidazole derived thiosemicarbazones and hydrazones were prepared by condensation of 4(5)-imidazole carboxaldehyde, 4-(1H-imidazole-1-yl)benzaldehyde and 4-(1H-imidazole-1-yl)acetophenone with a thiosemicarbazide or hydrazide. All compounds were characterized by quantitative elemental analysis, IR and NMR techniques. Eight structures were determined by single crystal X-ray diffraction. The antifungal activities of the compounds were evaluated. None of the compounds exhibited significant activity against Aspergillus flavus and Candida albicans, while 4(5)-imidazolecarboxaldehyde thiosemicarbazone (ImT) and 4-(1H-imidazole-1-yl)benzaldehyde thiosemicabazone (4ImBzT) were highly and selectively active against Cladosporium cladosporioides. 4(5)-Imidazolecarboxaldehyde benzoyl hydrazone (4(5)ImPh), 4(5)-imidazolecarboxaldehyde-para-chlorobenzoyl hydrazone (4(5)ImpClPh), 4(5)-imidazolecarboxaldehyde-para-nitrobenzoyl hydrazone (4(5)ImpNO2Ph), 4-(imidazole-1-yl)acetophenone-para-chloro-benzoyl hydrazone (4ImAcpClPh) and 4-(imidazole-1-yl)acetophenone-para-nitro-benzoylhydrazone (4ImAcpNO2Ph) were highly active against Candida glabrata. 4(5)ImpClPh and 4(5)ImpNO2Ph were very effective against C. cladosporioides. In many cases, activity was superior to that of the reference compound nystatin.
Keywords: imidazole; hydrazones; thiosemicarbazones; antifungal activity imidazole; hydrazones; thiosemicarbazones; antifungal activity
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.


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Reis, D.C.; Despaigne, A.A.R.; Silva, J.G.D.; Silva, N.F.; Vilela, C.F.; Mendes, I.C.; Takahashi, J.A.; Beraldo, H. Structural Studies and Investigation on the Activity of Imidazole-Derived Thiosemicarbazones and Hydrazones against Crop-Related Fungi. Molecules 2013, 18, 12645-12662.

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