Synthesis and bioactivity of pyrazole acyl thiourea derivatives.

Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry
Jian WuDe-Yu Hu

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.

References

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Sep 18, 2007·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Yin-Pu LvDe-Yu Hu
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Citations

Oct 11, 2013·Acta Crystallographica. Section E, Structure Reports Online·R SanthakumariBohari M Yamin
Oct 15, 2014·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Valentina AnutaOctavian Tudorel Olaru
Jul 19, 2013·Pest Management Science·Wen-Qun LiLi-Ting Yan
Jan 4, 2015·European Journal of Medicinal Chemistry·Ş Güniz Küçükgüzel, Sevil Şenkardeş
Mar 13, 2018·Organic & Biomolecular Chemistry·L Roopesh KumarVommina V Sureshbabu
Jan 13, 2015·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Jin-Jing XiaoHai-Qun Cao
Jan 13, 2018·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Khalid KarrouchiM'hammed Ansar
Mar 29, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Carmen LimbanDiana Camelia Nuta
May 7, 2020·Chemistry & Biodiversity·Olena V KholodniakKarl G Steffens
Jun 24, 2017·Acta Crystallographica. Section E, Crystallographic Communications·Arunpatcha Nimthong-RoldánYupa Wattanakanjana
Jan 14, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·András Gy NémethPéter Ábrányi-Balogh
Mar 4, 2021·International Journal of Molecular Sciences·Daylin Fernández PachecoYamilet Coll García

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Methods Mentioned

BETA
NMR
column chromatography

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