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. 2016 Jan 8;21(1):68.
doi: 10.3390/molecules21010068.

Design, Synthesis, DFT Study and Antifungal Activity of Pyrazolecarboxamide Derivatives

Jin-Xia Mu  1 , Yan-Xia Shi  2 , Ming-Yan Yang  3 , Zhao-Hui Sun  4 , Xing-Hai Liu  5 , Bao-Ju Li  6 , Na-Bo Sun  7
Affiliations

Design, Synthesis, DFT Study and Antifungal Activity of Pyrazolecarboxamide Derivatives

Jin-Xia Mu et al. Molecules. .

Abstract

A series of novel pyrazole amide derivatives were designed and synthesized by multi-step reactions from phenylhydrazine and ethyl 3-oxobutanoate as starting materials, and their structures were characterized by NMR, MS and elemental analysis. The antifungal activity of the title compounds was determined. The results indicated that some of title compounds exhibited moderate antifungal activity. Furthermore, DFT calculations were used to study the structure-activity relationships (SAR).

Keywords: DFT; SAR; antifungal activity; pyrazole; synthesis.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
The commercial pyrazole amide fungicides.
Scheme 1
Scheme 1
Design strategy of the title compounds.
Figure 2
Figure 2
Frontier molecular orbitals of compound 5h and penflufen.
Figure 3
Figure 3
Overlay of energy-minimized structures of 5h and penflufen.
Scheme 2
Scheme 2
The synthetic route of title compounds. Reagents and Condition: i. EtOH, reflux, 4 h, 83%; ii. POCl3/DMF, 0–5 °C to 120 °C, 1.5 h, 85%; iii. a. KMnO4 H2O, MW, 0.5 h; b. HCl, 95%; iv. SOCl2, reflux, 2 h; v. RNH2, THF, Et3N, r.t., 8 h.
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