Isatin‐1,2,3‐triazole‐isatin Scaffolds and Their Antibacterial Activity

Abstract

Twelve novel isatin‐1,2,3‐triazole‐isatin scaffolds 5a–l were designed, synthesized, and assessed for their in vitro antibacterial activity in this paper. The preliminary results showed that all dimers only endowed with weak antibacterial activity, which was less active than the reference ciprofloxacin. However, the structure–activity relationship was enriched, which may be useful for the further development of more efficient candidates.

A Comprehensive Review of the Diverse Spectrum Activity of 1,2,3‐Triazole‐linked Isatin Hybrids

“…Cheng et al [78] . successfully fabricated a novel library of isatin‐1,2,3‐triazole linked isatin hybrids which demonstrated antibacterial activity with reference CPFX (ciprofloxacin) against various clinically important bacteria by twofold agar dilution method.…”

“…(Reproduced from ref. [78] Copyright (2019), with permission from Elsevier) respectively, as compared to the standard drug fluconazole. Hybrids 145 and 146 synthesized using isatin-linked alkyne 142 and different aryl azides 143 and 144 in one pot using a CuAAC reaction (Scheme 46).…”

“…Cheng et al [78] successfully fabricated a novel library of isatin-1,2,3-triazole linked isatin hybrids which demonstrated antibacterial activity with reference CPFX (ciprofloxacin) against various clinically important bacteria by twofold agar dilution method. Compound 138 was found to be not so much superior towards first-line antibacterial agent CPFX against various tested strains such as MSSE, MRSE, MSSA, MRSA, etc, but enriched SAR studies might be useful for further development towards efficient hybrids.…”

Isatin dimers and their biological activities

“…Incorporation of the 1,2,3‐triazole fragment between the two isatin moieties could not enhance the antibacterial activity of isatin dimers as evidenced by the fact that dimers 2 (Figure 2; MIC: 64 to >256 μg/ml) also exhibited weak to moderate activity against 14 Gram‐positive and ‐negative bacteria, and the activity was far less potent than that of ciprofloxacin (MIC: 0.25–32 μg/ml). [ 27 ] Further study suggested that the introduction of neither the electron‐withdrawing nor ‐donating group into C‐5 position (R 1 ) of the isatin skeleton could improve the activity, and replacement of ketone at the C‐3 position (R 2 ) by imine led to the loss of activity. In particular, dimer 2a (MIC: 128 μg/ml) showed the highest activity against MSSE, MRSE, MSSA, and MRSA strains, and it could act as a lead molecule for further modification.…”

Fluorinated-Triazole-Modified ZnO and Its Application in Marine Antifouling

“…Dimitrakellis [20] et al pointed out that a low surface energy antifouling coating with new nano−antibacterial filler can achieve the effect of antibiological attachment and the dual development of an "active" antibacterial. In previous studies, the triazole ring structure widely used in biopharmaceutics can destroy the biomass membrane [21][22][23][24][25][26][27], which is usually combined with fluorine to achieve a synergistic antibacterial mechanism. The fluorine's strong electronegativity and hydrogen−like mimic effect [28][29][30][31][32] harm bacterial reproduction and growth.…”