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Synthesis and Bioactivity of Pyrazole Acyl Thiourea Derivatives
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; in revised form: 19 April 2012 / Accepted: 19 April 2012 / Published: 3 May 2012
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
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MDPI and ACS Style
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.
Wu J, Shi Q, Chen Z, He M, Jin L, Hu D. Synthesis and Bioactivity of Pyrazole Acyl Thiourea Derivatives. Molecules. 2012; 17(5):5139-5150.
Wu, Jian; Shi, Qing; Chen, Zhuo; He, Ming; Jin, Linhong; Hu, Deyu. 2012. "Synthesis and Bioactivity of Pyrazole Acyl Thiourea Derivatives." Molecules 17, no. 5: 5139-5150.