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Synthesis, biological activities and 3D-QSAR studies of (R)-2-phenyl-4,5-dihydrothiazole-4-carboxamide derivatives containing a sulfur ether moiety
- Source :
- Chinese Chemical Letters. 30:668-671
- Publication Year :
- 2019
- Publisher :
- Elsevier BV, 2019.
-
Abstract
- A series of (R)-2-phenyl-4,5-dihydrothiazole-4-carboxamide derivatives containing a sulfur ether moiety were synthesized and characterized on the basis of NMR and elemental analysis (EA). The crystal structure of (R)-N-(2-methyl-1-(methylthio)propan-2-yl)-2-(4-nitrophenyl)-4,5-dihydrothiazole-4-carboxamide (13d) was determined to show R configuration. The bioasssy results indicated that most title compounds displayed good and broad spectrum antifungal activities against several phytopathogenic fungi. The structure activity relationships were discussed. Based on the antifungal activity of title compounds against Phytophthora capsici, a CoMSIA calculation was performed to establish a 3D-QSAR model, which revealed that electrostatic and hydrophobic fields were the two most significant factors for antifungal activity. According to the established 3D-QSAR model, structure optimization was carried out to find (R)-N-((R)-1-(methylthio)propan-2-yl)-2-(p-tolyl)-4,5-dihydrothiazole-4-carboxamide (15h) with excellent activity against Phytophthora capsici, thus emerging as a new lead compound for novel antiphytopathogenic fungus agent development.
- Subjects :
- Quantitative structure–activity relationship
biology
medicine.drug_class
Stereochemistry
chemistry.chemical_element
Ether
Carboxamide
02 engineering and technology
General Chemistry
Crystal structure
010402 general chemistry
021001 nanoscience & nanotechnology
biology.organism_classification
01 natural sciences
Sulfur
0104 chemical sciences
chemistry.chemical_compound
Phytophthora capsici
chemistry
medicine
Moiety
0210 nano-technology
Lead compound
Subjects
Details
- ISSN :
- 10018417
- Volume :
- 30
- Database :
- OpenAIRE
- Journal :
- Chinese Chemical Letters
- Accession number :
- edsair.doi...........9fa9a277636926fe97e0cb07ec692a7e