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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(1 H )‐selenone derivatives
Author(s) -
Żesławska Ewa,
Korona-Głowniak Izabela,
Nitek Wojciech,
Tejchman Waldemar
Publication year - 2020
Publication title -
acta crystallographica section c
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.304
H-Index - 17
ISSN - 2053-2296
DOI - 10.1107/s2053229620004040
Subject(s) - substituent , chemistry , monoclinic crystal system , intermolecular force , intramolecular force , hydrogen bond , molecule , stereochemistry , crystallography , crystal structure , methyl group , group (periodic table) , organic chemistry
Derivatives of pyrimidine‐2(1 H )‐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(1 H )‐selenones ( X = 2, 3 and 4 for 1 , 2 and 3 , respectively), C 18 H 16 N 2 OSe, showed very strong activity against selected strains of Gram‐positive bacteria and fungi. Two compounds, 1 and 2 , crystallize in the monoclinic space group P 2 1 / c , while 3 crystallizes in the space group P 2 1 / n ; 1 has two molecules in the asymmetric unit and the other two ( 2 and 3 ) have one molecule. The geometries of the investigated compounds differ slightly in the mutual orientations of the aromatic and pyrimidineselenone rings. The O atom in 1 stabilizes the conformation of the molecules via intramolecular C—H…O hydrogen bonding. The packing of molecules is determined by weak C—H…N and C—H…Se intermolecular interactions and additionally in 1 and 2 by C—H…O intermolecular interactions. The introduction of the methoxy substituent results in greater selectivity of the investigated compounds.