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Sterically Hindered N ‐Heterocyclic Salts Utilized as Antimicrobial Agents
Author(s) -
Ndlovu Slindile N. P.,
Ibrahim Halliru,
Bala Muhammad D.
Publication year - 2017
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.2992
Subject(s) - chemistry , antimicrobial , steric effects , iodide , bacillus subtilis , salmonella enterica , enterococcus faecalis , escherichia coli , medicinal chemistry , stereochemistry , bacteria , organic chemistry , biochemistry , biology , gene , genetics
By the adoption of annulated ring systems for their steric bulkiness, a new series of symmetric N ‐heterocyclic imidazolium and perimidium salts were synthesized. Also, corresponding asymmetric ferrocenyl N ‐functionalized series were prepared as salts. All the reported salts were fully characterized. The reported X‐ray structure of 4,5‐diphenyl‐1,3‐dimethyl‐1 H ‐imidazol‐3‐ium iodide ( 2a ) shows that it crystallized in the orthorhombic space group P 2 1 2 1 2 1 . Low to moderate antimicrobial activities were observed with both sets of salts against important clinical isolates of Staphylococcus aureus , Bacillus subtilis , and Enterococcus faecalis and Escherichia coli , Pseudomonas aeruginosa , and Salmonella enterica . The results were benchmarked against meropenem. Both 1,3‐propyl‐1 H ‐phenanthro[9,10‐ d ]imidazol‐3‐ium iodide ( 3b ) and 1‐ferrocenyl‐3‐propyl‐1 H ‐perimidin‐3‐ium iodide ( 9b ) showed high antimicrobial activities against all tested Gram‐positive bacterial strains, with minimum inhibitory concentration values ranging from 8 to 4 μg/mL (meropenem = 0.5–0.125 μg/mL), while all the salts showed little or no activity against Gram‐negative bacterial strains. In general, the asymmetric ferrocenyl‐containing salts exhibited higher activities than the symmetric ones.