Synthesis and Bioactivity of Pyrazole Acyl Thiourea Derivatives
Sixteen novel pyrazole acyl thiourea derivatives <strong>6</strong> were synthesized from monomethylhydrazine (phenylhydrazine) and ethyl acetoacetate. The key 5-chloro-3-methyl-1-substituted-1<em>H</em>-pyrazole-4-carbonyl chloride intermediat...
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doaj-ffedb0a335a24a1eba70b883e482dd7c2020-11-24T23:20:59ZengMDPI AGMolecules1420-30492012-05-011755139515010.3390/molecules17055139Synthesis and Bioactivity of Pyrazole Acyl Thiourea DerivativesJian WuLinhong JinQing ShiDeyu HuMing HeZhuo ChenSixteen novel pyrazole acyl thiourea derivatives <strong>6</strong> were synthesized from monomethylhydrazine (phenylhydrazine) and ethyl acetoacetate. The key 5-chloro-3-methyl-1-substituted-1<em>H</em>-pyrazole-4-carbonyl chloride intermediates <strong>4</strong> 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-1<em>H</em>-pyrazole-4-carbonyl isothiocyanates <strong>5</strong>. Subsequent reaction with fluorinated aromatic amines resulted in the formation of the title compounds.<strong> </strong>The synthesized compound were unequivocally characterized by IR, <sup>1</sup>H-NMR, <sup>13</sup>C-NMR and elemental analysis and some of the synthesized compounds displayed good antifungal activities against <em>Gibberella zeae</em>, <em>Fusarium oxysporum</em>, <em>Cytospora mandshurica</em> and anti-TMV activity in preliminary antifungal activity tests.http://www.mdpi.com/1420-3049/17/5/5139pyrazole acyl thiourea derivativessynthesisantifungal activityantiviral activity |
collection |
DOAJ |
language |
English |
format |
Article |
sources |
DOAJ |
author |
Jian Wu Linhong Jin Qing Shi Deyu Hu Ming He Zhuo Chen |
spellingShingle |
Jian Wu Linhong Jin Qing Shi Deyu Hu Ming He Zhuo Chen Synthesis and Bioactivity of Pyrazole Acyl Thiourea Derivatives Molecules pyrazole acyl thiourea derivatives synthesis antifungal activity antiviral activity |
author_facet |
Jian Wu Linhong Jin Qing Shi Deyu Hu Ming He Zhuo Chen |
author_sort |
Jian Wu |
title |
Synthesis and Bioactivity of Pyrazole Acyl Thiourea Derivatives |
title_short |
Synthesis and Bioactivity of Pyrazole Acyl Thiourea Derivatives |
title_full |
Synthesis and Bioactivity of Pyrazole Acyl Thiourea Derivatives |
title_fullStr |
Synthesis and Bioactivity of Pyrazole Acyl Thiourea Derivatives |
title_full_unstemmed |
Synthesis and Bioactivity of Pyrazole Acyl Thiourea Derivatives |
title_sort |
synthesis and bioactivity of pyrazole acyl thiourea derivatives |
publisher |
MDPI AG |
series |
Molecules |
issn |
1420-3049 |
publishDate |
2012-05-01 |
description |
Sixteen novel pyrazole acyl thiourea derivatives <strong>6</strong> were synthesized from monomethylhydrazine (phenylhydrazine) and ethyl acetoacetate. The key 5-chloro-3-methyl-1-substituted-1<em>H</em>-pyrazole-4-carbonyl chloride intermediates <strong>4</strong> 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-1<em>H</em>-pyrazole-4-carbonyl isothiocyanates <strong>5</strong>. Subsequent reaction with fluorinated aromatic amines resulted in the formation of the title compounds.<strong> </strong>The synthesized compound were unequivocally characterized by IR, <sup>1</sup>H-NMR, <sup>13</sup>C-NMR and elemental analysis and some of the synthesized compounds displayed good antifungal activities against <em>Gibberella zeae</em>, <em>Fusarium oxysporum</em>, <em>Cytospora mandshurica</em> and anti-TMV activity in preliminary antifungal activity tests. |
topic |
pyrazole acyl thiourea derivatives synthesis antifungal activity antiviral activity |
url |
http://www.mdpi.com/1420-3049/17/5/5139 |
work_keys_str_mv |
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1725573395200868352 |