synthesis and bioactivity of pyrazole acyl thiourea derivatives合成和生物活性的吡唑酰基硫脲衍生品.pdfVIP

Molecules 2012, 17, 5139-5150; doi:10.3390/molecule OPEN ACCESS molecules ISSN 1420-3049 /journal/molecules Article Synthesis and Bioactivity of Pyrazole Acyl Thiourea Derivatives Jian Wu †, Qing Shi †, Zhuo Chen, Ming He, Linhong Jin and Deyu Hu * 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; E-Mails: jianwu2691@ (J.W.); shiqing982816@163.com (Q.S.); fcc.zchen@ (Z.C.); hmher@126.com (M.H.); fcc.jinlh@ (L.J.) † These authors contributed equally to this work. * Author to whom correspondence should be addressed; E-Mail: fcc.dyhu@; Tel./Fax: +86-851-829-2170. 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