Abstract
A series of N-acylated analogues of 1-isopropyl-3-acyl-5-methyl-benzimidazolone were synthesized. Bioassay results indicated that analogues 5-07 and 5-19 exhibited the most potency against Bacillus cereus, Bacillus subtilis, Staphylococcus aureus, Escherichia coli and Pseudomonas aeruginosa. Analogues 5-02, 5-07, 5-12, 5-15, 5-19, 5-20 and 5-25 could effectively inhibit the spore germination of Botrytis cinerea. The relationship between structure and their antimicrobial activity (SAR) has also been discussed according to aliphatic acids and aromatic acids derivatives, respectively. This implied that the N-acylated derivatives of 5-methyl-benzimidazolone might be potential antimicrobial agents.
Highlights
Benzimidazolone and their derivatives are useful intermediates in the production of pharmaceuticals and pesticides [1]
With the aim of studying the structure–activity relationship
The minimum inhibitory concentration (MIC) values of these three compounds were determined by the method of micro-broth dilution, and the results indicated that 5-07 had the most strong inhibitory action; its MICs against B. cereus, B. subtilis, S. aureus, E. coli and P. aeruginosa were 25.0, 12.5, 50.0, 50.0 and 100.0 μg/mL, respectively (Table 2)
Summary
Benzimidazolone and their derivatives are useful intermediates in the production of pharmaceuticals and pesticides [1]. Benzimidazolone carboxylic acids derivatives are potential therapeutic agents of selective peroxisome proliferator-activated receptor γ modulators (SPPARγMs) and are useful for the treatment of type II diabetes mellitus (T2DM) [2]. There are several reports on the antimicrobial activity of benzimidazolones It has been reported in recent literature that benzimidazolones, which contain a sugar residue or piperidine ring, exhibited antibacterial activities to several strains of Gram-positive or Gram-negative bacteria [12,13]. We synthesized a series of N-acylated isopropenyl-benzimidazolones (Figure 1), in which several derivatives exhibited strong antifungal activity against Botrytis cinerea [14,15,16]. To better reveal the relationship between the structures and their antimicrobial activities of benzimidazolones, especially the influence of introducing substituted groups to the benzene ring, a series of N-acylated analogues of 1-isopropyl-3-acyl-5-methyl-benzimidazolone were synthesized and evaluated for antimicrobial activity
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