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Effect of the position of a methoxy substituent on the antimicrobial activity and crystal structures of 4-methyl-1,6-diphenylpyrimidine-2(1H)-selenone derivatives
- Source :
- Acta crystallographica. Section C, Structural chemistry. 76(Pt 4)
- Publication Year :
- 2019
-
Abstract
- Derivatives of pyrimidine-2(1H)-selenone are a group of compounds with very strong antimicrobial activity. In order to study the effect of the position of the methoxy substituent on biological activity, molecular geometry and intermolecular interactions in the crystal, three derivatives were prepared and evaluated with respect to their antimicrobial activities, and their crystal structures were determined by X-ray diffraction. The investigated compounds, namely, 1-(X-methoxyphenyl)-4-methyl-6-phenylpyrimidine-2(1H)-selenones (X= 2, 3 and 4 for1,2and3, respectively), C18H16N2OSe, showed very strong activity against selected strains of Gram-positive bacteria and fungi. Two compounds,1and2, crystallize in the monoclinic space groupP21/c, while3crystallizes in the space groupP21/n;1has two molecules in the asymmetric unit and the other two (2and3) have one molecule. The geometries of the investigated compounds differ slightly in the mutual orientations of the aromatic and pyrimidineselenone rings. The O atom in1stabilizes the conformation of the moleculesviaintramolecular C—H...O hydrogen bonding. The packing of molecules is determined by weak C—H...N and C—H...Se intermolecular interactions and additionally in1and2by C—H...O intermolecular interactions. The introduction of the methoxy substituent results in greater selectivity of the investigated compounds.
- Subjects :
- crystal structure
antifungal
Substituent
Crystal structure
010402 general chemistry
Crystallography, X-Ray
01 natural sciences
Inorganic Chemistry
Crystal
chemistry.chemical_compound
Anti-Infective Agents
Position (vector)
Group (periodic table)
Materials Chemistry
Physical and Theoretical Chemistry
pyrimidineselenone
Molecular Structure
antimicrobial
010405 organic chemistry
Hydrogen bond
Fungi
Hydrogen Bonding
hydrogen bonding
Condensed Matter Physics
antibacterial
0104 chemical sciences
Crystallography
Pyrimidines
chemistry
Selectivity
Monoclinic crystal system
Subjects
Details
- ISSN :
- 20532296
- Volume :
- 76
- Issue :
- Pt 4
- Database :
- OpenAIRE
- Journal :
- Acta crystallographica. Section C, Structural chemistry
- Accession number :
- edsair.doi.dedup.....af03865d3615a414a7253a9330bf5819