Synthesis of 2-(4-methyl-1,3-thiazol-5-yl)ethyl esters of acridone carboxylic acids and evaluation of their antibacterial activity

Recent developments in the synthesis and biological activity of acridine/acridone analogues

“…70 Derivative (100k, Scheme 14) exhibited more effective activity against S. enteritidis than erythromycin, 72 while derivative (103b, Scheme 15) exhibited higher activity against Candida albicans than Rivanol. 73 Compounds (121a, 136l, 143e, 146c, 158b, 158f, 158i, 158j, 186d) showed promising antitumour activity against HepG-2 (ref. 15, 30, 85, 87, 95 and 105) Additionally, derivatives (136l, 143e, 146c, 186d) exhibited good activity results against K562 through binding with DNA and inhibiting topo I activity.…”

“…72 Markovich et al presented the synthesis of 2-(4-methyl-1,3thiazol-5-yl)ethyl esters of acridone carboxylic acids (103a-g) by the transesterication of the corresponding butyl esters of acridone carboxylic acids (101a-g) with 5-(2-hydroxyethyl)-4methylthiazole (102) in the presence of sodium methoxide as the catalyst (Scheme 15). 73 Analogues of acridone that have a carboxyl group directly bonded to the aromatic ring of acridone also exhibit biological activity. [74][75][76] Therefore, 2-(4-methyl-1,3-thiazol-5-yl)ethyl esters of 2(4)-carboxyacridone (106)(107) were prepared.…”

“…[74][75][76] Therefore, 2-(4-methyl-1,3-thiazol-5-yl)ethyl esters of 2(4)-carboxyacridone (106)(107) were prepared. 73 The reaction was carried out at 70 C for 1 h using 2-or 4-carboxyacridone acid chloride (104-105) and 5-(2-hydroxyethyl)-4-methylthiazole (102) (Scheme 16). 73 Compounds (103a-b and 107) were tested for antibacterial activity against strains of microorganisms (E. coli, Ps.…”

“…Moreover, derivative (103b) with a CH 3 group at the 2-position of the acridone moiety showed slightly higher activity against Candida albicans in comparison to Rivanol. 73 Bhardwaj et al synthesized new acridone derivatives. Acridone was coupled via a linker group to an anti-inammatory (AI) drug such as ibuprofen (109), (S)-naproxen (110), acetyl salicylic acid (108) or chlororofecoxib analogue (114).…”

‘Acridines’ as New Horizons in Antifungal Treatment

“…These compounds were tested for antimicrobial activity against bacterial (P. aeruginosa, E. coli, Proteus vulgaris, S. aureus, and Bacillus subtilis) and fungal (C. albicans) strains. The prepared analogues were active and showed inhibition against all evaluated microorganisms [14]. Acridine thiosemicarbazide derivatives ( Figure 2C) exhibited both antibacterial and antifungal activity (minimal inhibitory concentration (MIC) range 10-80 µM) as well as anticancer activity (IC50 range 10-70 µM) [15].…”