Crystal structure and molecular docking studies of new pyrazole-4-carboxamides

Li Qiao,Peng-Peng Cai,Zhong-Hua Shen,Hong-Ke Wu,Xing-Hai Liu,Jian-Quan Weng,Cheng-Xia Tan

doi:10.1515/hc-2019-0012

Abstract

AbstractTwo pyrazol-4-carboxamides, 3-(difluoromethyl)-N-(mesitylcarbamoyl)-1-methyl-1H-pyrazole-4-carboxa-mide (7a) and 3-(difluoromethyl)-N-((3,5-dimethylphenyl) carbamoyl)-1-methyl-1H-pyrazole-4-carboxamide (7b) were synthesized and their structures were confirmed by the aid of 1H NMR and HRMS analyses. The structure of the pyrazole-4-carboxamide, 7a was also determined by X-ray diffraction. The preliminary activity results demonstrate that these two compounds exhibit good inhibitory activity against Botrytis cinerea. Further docking results indicated that the key active group is difluoromethyl pyrazole moiety.

Highlights

Two pyrazol-4-carboxamides, 3-(difluoromethyl)N-(mesitylcarbamoyl)-1-methyl-1H-pyrazole-4-carboxamide (7a) and 3-(difluoromethyl)-N-((3,5-dimethylphenyl) carbamoyl)-1-methyl-1H-pyrazole-4-carboxamide (7b) were synthesized and their structures were confirmed by the aid of 1H NMR and HRMS analyses
The compounds with urea group exhibited diversity bioactivities, such as mosquito [21], antimicrobial [22], antiviral [23], antifungal [24,25,26] and antinociceptive activity [27]. In view of these facts mentioned above, and as a part of our work on the synthesis of bioactive lead compounds for drug discovery [28,29,30,31,32,33,34,35,36,37,38,39,40,41,42,43,44,45,46], two new pyrazole-4-carboxamides, 3-(difluoromethyl)-N(mesitylcarbamoyl)-1-methyl-1H-pyrazole-4-carboxamide (7a) and 3-(difluoromethyl)-N-((3,5-dimethylphenyl) carbamoyl)-1-methyl-1H-pyrazole-4-carboxamide (7b) were designed and synthesized
The results indicated that the key active group is difluoromethyl pyrazole moiety

Summary

Introduction

Two pyrazol-4-carboxamides, 3-(difluoromethyl)N-(mesitylcarbamoyl)-1-methyl-1H-pyrazole-4-carboxamide (7a) and 3-(difluoromethyl)-N-((3,5-dimethylphenyl) carbamoyl)-1-methyl-1H-pyrazole-4-carboxamide (7b) were synthesized and their structures were confirmed by the aid of 1H NMR and HRMS analyses. The structure of the pyrazole-4-carboxamide, 7a was determined by X-ray diffraction. The single crystal structure of compound 7a was determined by X-ray diffraction.

Results

Conclusion