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Molecules 2012, 17(5), 5139-5150; doi:10.3390/molecules17055139
Article

Synthesis and Bioactivity of Pyrazole Acyl Thiourea Derivatives

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State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agriculture Bioengineering, Ministry of Education, Guizhou University, Guiyang 550025, China These authors contributed equally to this work.
* Author to whom correspondence should be addressed.
Received: 11 April 2012 / Revised: 19 April 2012 / Accepted: 19 April 2012 / Published: 3 May 2012
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Abstract

Sixteen novel pyrazole acyl thiourea derivatives 6 were synthesized from monomethylhydrazine (phenylhydrazine) and ethyl acetoacetate. The key 5-chloro-3-methyl-1-substituted-1H-pyrazole-4-carbonyl chloride intermediates 4 were first generated in four steps through cyclization, formylation, oxidation and acylation. Thess were then reacted with ammonium thiocyanate in the presence of PEG-400 to afford 5-chloro-3-methyl-1-substituted-1H-pyrazole-4-carbonyl isothiocyanates 5. Subsequent reaction with fluorinated aromatic amines resulted in the formation of the title compounds. The synthesized compound were unequivocally characterized by IR, 1H-NMR, 13C-NMR and elemental analysis and some of the synthesized compounds displayed good antifungal activities against Gibberella zeae, Fusarium oxysporum, Cytospora mandshurica and anti-TMV activity in preliminary antifungal activity tests.
Keywords: pyrazole acyl thiourea derivatives; synthesis; antifungal activity; antiviral activity pyrazole acyl thiourea derivatives; synthesis; antifungal activity; antiviral 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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Wu, J.; Shi, Q.; Chen, Z.; He, M.; Jin, L.; Hu, D. Synthesis and Bioactivity of Pyrazole Acyl Thiourea Derivatives. Molecules 2012, 17, 5139-5150.

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