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

Synthesis and Bioactivity of Pyrazole Acyl Thiourea Derivatives

Jian Wu † email, Qing Shi † email, Zhuo Chenemail, Ming Heemail, Linhong Jinemail and Deyu Hu* email
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
PDF Full-text Download PDF Full-Text [269 KB, uploaded 3 May 2012 10:33 CEST]
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

Article Statistics

Click here to load and display the download statistics.

Cite This Article

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.

AMA Style

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.

Chicago/Turabian Style

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.

Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert