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Synthesis and fungicidal activity of novel 2-(2-alkylthio-6-phenylpyrimidin-4-yl)-1H-benzimidazoles
- Source :
- Bioorganic & Medicinal Chemistry Letters. 47:128210
- Publication Year :
- 2021
- Publisher :
- Elsevier BV, 2021.
-
Abstract
- With the aim of exploring new benzimidazole derivative with high fungicidal activity, a series of novel 2-(2-(alkylthio)-6-phenylpyrimidin-4-yl)-1H-benzimidazoles were designed and synthesized, and their in vitro fungicidal activities were evaluated. Compounds 5a, 5f, 5g, 5h, 5i and 5l exhibited excellent fungicidal activities against Botrytis cinerea, and 5c, 5f, 5h, 5i and 5l displayed notable fungicidal activities against Sclerotinia sclerotiorum. Among them, compound 5i (R1 = fluorine, R2 = benzyl) displayed the best activity towards the two tested fungi. Docking study of 5i with β-tubulin protein revealed that the NH moiety of benzimidazole ring generated a hydrogen bond with Gln-11 residue, and the fluorine atom of benzene ring formed a hydrogen bond with Tyr-208 residue, respectively; the benzene ring of Tyr-222 and the pyrimidine ring of 5i yielded a π-π interaction. The molecular electrostatic potential analysis elucidated the nitrogen atom of benzimidazole ring, fluorine atom of benzene ring and sulfur atom of thioether moiety were located in the negative potential regions, whereas some hydrogen atoms of benzene, benzimidazole and pyrimidine rings were located in the positive potential regions. This analysis demonstrated the reason why 5i can form hydrogen bonds with amino acid residues of target protein.
- Subjects :
- Benzimidazole
Antifungal Agents
Pyrimidine
Clinical Biochemistry
Pharmaceutical Science
Microbial Sensitivity Tests
Ring (chemistry)
01 natural sciences
Biochemistry
Medicinal chemistry
Structure-Activity Relationship
chemistry.chemical_compound
Residue (chemistry)
Fusarium
Thioether
Drug Discovery
Moiety
Benzene
Molecular Biology
Dose-Response Relationship, Drug
Molecular Structure
010405 organic chemistry
Hydrogen bond
Organic Chemistry
Fungicides, Industrial
0104 chemical sciences
010404 medicinal & biomolecular chemistry
chemistry
Molecular Medicine
Benzimidazoles
Pyricularia grisea
Subjects
Details
- ISSN :
- 0960894X
- Volume :
- 47
- Database :
- OpenAIRE
- Journal :
- Bioorganic & Medicinal Chemistry Letters
- Accession number :
- edsair.doi.dedup.....f8c68c3804debcd73a1ddabf4cad817b