Synthesis and antimycobacterial evaluation of new (2-oxo-2H-chromen-3-yl) substituted fluoroquinolones

Fluoroquinolones’ Biological Activities against Laboratory Microbes and Cancer Cell Lines

“…However, a wide range in ciprofloxacin MIC against E. coli ATCC 25922 is perturbing as MIC reported ranged from 0.002 µM [ 24 ]−61.869 µM [ 49 ] in different publications. This fluctuation in ciprofloxacin antibacterial activities may explain the current abundant application of levofloxacin and moxifloxacin as positive standards by medicinal chemists when designing and synthesizing novel FQs analogues [ 24 , 28 , 53 , 54 , 55 , 68 , 69 , 70 , 73 , 74 , 75 ].…”

“…FQs, particularly ciprofloxacin was included as a positive control along with isoniazid and rifampicin against various Mycobacterium strains as shown in Table 5 [ 24 , 26 , 27 , 28 , 58 , 63 , 65 , 68 , 75 , 81 , 82 ]. Furthermore, levofloxacin in vitro anti-mycobacterial activity was reported and found to be comparable to ciprofloxacin [ 26 , 68 ].…”

“…However, a wide range in ciprofloxacin MIC against E. coli ATCC 25922 is perturbing as MIC reported ranged from 0.002 µM [24]−61.869 µM [49] in different publications. This fluctuation in ciprofloxacin antibacterial activities may explain the current abundant application of levofloxacin and moxifloxacin as positive standards by medicinal chemists when designing and synthesizing novel FQs analogues [24,28,[53][54][55][68][69][70][73][74][75]. <1.811 [28,63] 0.024 [54,57] 0.031 [48] 0.010 [66] 61.869 [49] 0.091 [62] 0.002 [24] NR 17663 0.002 [24] NR 17666 0.045 [24] NR 17661 96.577 [24] ATCC 25922 ESBLs(-); ≤0.091 [55] ≤0.080 [51] ATCC 25922 (wild type) ≤ 0.091 [76] ATCC 35218 0.045 [60,61] 16.961 [34] ≤0.080 [51] BW5328/pAH69 (wild type) ≤ 0.091 [76] CAN-ICU 61714 (GEN-R) ≤0.755 [21] CAN-ICU 63074 (AMK 32) ≤0.755 [21] CANWARD-2011 97615 772.616 [21] gyrA <0.018 [69] 0.037 [24] <1.370 [28] NR 17663 0.037 [24] NR 17666 0.075 [24] NR 17661 79.715 [24] 12-6 As presented in Table…”

Cyanomethylquinolones as a New Class of Potential Multitargeting Broad-Spectrum Antibacterial Agents

“…Compared to the cyano group, which directly bonds with the quinolone skeleton, a cyanomethyl group would more likely squeeze into the small cavities of the enzymes owing to the presence of flexible methylene and might result in stronger binding. A few cyanomethyl-containing quinolones II were prepared via simple and efficient reactions; however, their biological activity was not further evaluated, and they were simply used as synthetic intermediates of clinical antibacterial drugs (such as pazufloxacin). − Our study identified their excellent bioactivity against the ESKAPE pathogens, and the corresponding results enrich the information on their structure–activity relationship. Various substituents, including saturated and unsaturated alkyl groups, cycloalkyl and heterocyclic moieties, and benzyl and heteroaryl fragments, were incorporated at the N -1 position to adjust the lipid and water partition coefficient, scaffold rigidity, charge distribution, and the ability to penetrate the cell membrane, and their effects on the antibacterial activity were analyzed.…”

N-Arylation of 3-Formylquinolin-2(1H)-ones Using Copper(II)-Catalyzed Chan–Lam Coupling

“…The N -arylation of quinolines, and specifically their 2-oxo derivatives (2-quinolones) 1 , is an emerging area; these N -heterocycles are important structural constituents of numerous naturally occurring compounds [ 17 ], and represent relevant synthetic scaffolds for the generation of compounds with interesting or useful biological properties, such as as anticancer [ 18 ], antimycobacterial [ 19 ], insecticidal [ 20 ], antibacterial [ 21 ], antifungal [ 22 ], antiparasitic agents [ 23 ], antiviral [ 24 ], antimalarial [ 25 ], antioxidant [ 26 ], and anti-inflammatory properties [ 27 ], among others [ 28 , 29 , 30 ]. Likewise, N -arylated 2-quinolones are a common motif in diverse bioactive molecules such as antimicrobials [ 31 ], anti-inflammatory drugs [ 32 ], sodium channel inhibitors [ 33 ], kinase inhibitors [ 34 , 35 ], and HIV inhibitors [ 36 ].…”