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Design, synthesis, and antifungal activity of novel cinnamon-pyrazole carboxamide derivatives
- Source :
- Drug Development Research. 79:307-312
- Publication Year :
- 2018
- Publisher :
- Wiley, 2018.
-
Abstract
- Hit, Lead & Candidate Discovery To discover succinate dehydrogenase inhibitors with a novel structure, we introduced cinnamic acid structure to optimize the lead structure 1 and synthesized four series of cinnamon-pyrazole carboxamide derivatives. The bioassay data showed that compounds (E)-N-(1-[4-chlorophenyl]-4-cyano-1H-pyrazol-5-yl)-3-(2-fluorophenyl) acrylamide (5III-d) and (E)-3-(2-chlorophenyl)-N-(1-[4-chlorophenyl]-4-cyano-1H-pyrazol-5-yl) acrylamide (5III-f) showed the significant antifungal activity against three fungi. In addition, 5III-d and 5III-f exhibited the excellent inhibitory effect against succinate dehydrogenase (SDH) enzymes with IC50 values ranging from 19.4 to 28.7 μM. The study demonstrates that the chlorine substituent group is present on both the phenyl and pyrazole rings that have a very good effect on the antifungal effect, and the compounds 5III-d and 5III-f can act as potential SDH inhibitors (SDHI) and throw a sprat for a new generation of SDHI.
- Subjects :
- 0301 basic medicine
Antifungal Agents
medicine.drug_class
Stereochemistry
Chemical structure
Quantitative Structure-Activity Relationship
Carboxamide
Pyrazole
01 natural sciences
Cinnamic acid
Rhizoctonia
03 medical and health sciences
chemistry.chemical_compound
Drug Discovery
Colletotrichum
medicine
Bioassay
Plant Diseases
chemistry.chemical_classification
biology
010405 organic chemistry
Succinate dehydrogenase
0104 chemical sciences
Molecular Docking Simulation
030104 developmental biology
Enzyme
chemistry
Cinnamates
Drug Design
Acrylamide
biology.protein
Carboxin
Subjects
Details
- ISSN :
- 02724391
- Volume :
- 79
- Database :
- OpenAIRE
- Journal :
- Drug Development Research
- Accession number :
- edsair.doi.dedup.....bf9c1d8057e9affc6e0ce937d7d3db68