Synthesis, biological evaluations and computational studies of N-(3-(-2-(7-Chloroquinolin-2-yl)vinyl) benzylidene)anilines as fungal biofilm inhibitors

Khan, Firoz A. Kalam; Kaduskar, Rashmi N.; Patil, Rajesh B.; Patil, Rajendra; Ansari, Siddique Akber; Alkahtani, Hamad M.; Almehizia, Abdulrahman A.; Shinde, Devanand B.; Sangshetti, Jaiprakash N.

doi:10.1016/j.bmcl.2018.12.046

Cited by 13 publications

(12 citation statements)

References 37 publications

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“…Compounds 32b (MIC ¼ 94.2 mg mL À1 ) and 32c (MIC ¼ 98.8 mg mL À1 ) also revealed good antifungal activity comparable to that of the standard drug uconazole (MIC ¼ 50.0 mg mL À1 ). Antibacterial activity detection against four types of bacteria, Escherichia coli, Pseudomonas aeruginosa, Bacillus subtilis and Staphylococcus aureus showed that they have potential antibacterial activity where all compounds except 32d were better than the standard drug ciprooxacin for Bacillus subtilis 129 (Fig. 20).…”

Section: Targeting Biolmsmentioning

confidence: 99%

Bacterial virulence factors: a target for heterocyclic compounds to combat bacterial resistance

et al. 2021

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Section: Targeting Biolmsmentioning

confidence: 99%

Bacterial virulence factors: a target for heterocyclic compounds to combat bacterial resistance

et al. 2021

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“…One major group of biofilm inhibitors, inspired by scaffolds found in natural products with reported activity, are a diverse range of heterocyclic containing families, which include indoles [ 64 , 65 , 66 , 67 , 68 , 69 , 70 , 71 ], 2-aminoimidazoles [ 72 , 73 , 74 , 75 , 76 , 77 , 78 , 79 , 80 , 81 , 82 , 83 , 84 , 85 , 86 , 87 , 88 , 89 ], phenazines [ 90 , 91 , 92 , 93 , 94 , 95 , 96 , 97 , 98 ], and quinolines [ 99 , 100 , 101 , 102 , 103 , 104 , 105 , 106 ]. These lead molecules are the results of significant medicinal chemistry effort to improve potency and other drug-like properties.…”

Section: Approaches To Discover Anti-biofilm Compoundsmentioning

confidence: 99%

Strategies and Approaches for Discovery of Small Molecule Disruptors of Biofilm Physiology

et al. 2021

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Biofilms, the predominant growth mode of microorganisms, pose a significant risk to human health. The protective biofilm matrix, typically composed of exopolysaccharides, proteins, nucleic acids, and lipids, combined with biofilm-grown bacteria’s heterogenous physiology, leads to enhanced fitness and tolerance to traditional methods for treatment. There is a need to identify biofilm inhibitors using diverse approaches and targeting different stages of biofilm formation. This review discusses discovery strategies that successfully identified a wide range of inhibitors and the processes used to characterize their inhibition mechanism and further improvement. Additionally, we examine the structure–activity relationship (SAR) for some of these inhibitors to optimize inhibitor activity.

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“…7‐Chloroquinoline scaffolds tethered to anilines through vinylbenzylidine motif could not result in fine antibacterial potencies, except for a few derivatives. [ 28 ] No single synthesized compound has exhibited good P. aeruginosa and S. aureus inhibitory properties. However, compound 27 (Figure 6) comprising 4‐chloroaniline motif has elicited a remarkable E. coli inhibitory property (MIC = 45 µg/ml), comparatively higher than ciprofloxacin (MIC = 50 µg/ml).…”

Section: Antibacterial Activitymentioning

confidence: 99%

“…Even in this activity, the hydrazide‐bridged 2‐methoxyquinline dimerization resulted in the maximum activity. Moderate‐to‐poor antifungal properties are noticed for styryl‐quinoline analogs, [ 28 ] wherein the electron‐withdrawing 4‐trifluorophenyl motif has led to the most promising antibiofilm potency of compound 111 (Figure 17) against C. albicans NCIM 3471, a comparatively (MIC = 51.2 µg/ml) diminished activity than the standard inhibitor (MIC = 40 µg/ml). However, the corresponding antifungal activity is poor (MIC = 174.4 µg/ml).…”

Section: Antifungal Activitymentioning

confidence: 99%

Recent update on antibacterial and antifungal activity of quinoline scaffolds

Dorababu¹

2020

Archiv der Pharmazie

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Although most of the heterocycles have been reported to possess a significant pharmacological activity, only a few of them, namely quinoline derivatives, have exhibited the finest biological activities. Despite the few medicinal properties of the plain quinoline molecule, its derivatives exhibit diverse pharmacological properties such as anticancer, anti‐inflammatory, antibacterial, antiviral, antifungal, antiprotozoal activities, and so on. The potential antimicrobial properties of the quinoline derivatives are evident from the decades of research on these derivatives. Owing to limitations like drug resistance, high cost, severe side effects, and less bioavailability of previously synthesized antimicrobial agents, these drugs have become obsolete in recent years. Hence, the design of more efficient antimicrobial drugs must be given topmost priority. A breakthrough in drug discovery is a must to prevent malevolent microbial diseases. Addressing all these issues, researchers have been continuously contributing to antimicrobial drug discovery. Herein, a short description of the pharmacology of antimicrobial agents such as antibacterials and antifungals synthesized recently is provided. The versatile derivatization of the quinoline moiety leading to significant antimicrobial potencies is discussed, considering the structure–activity relationship.

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Synthesis, biological evaluations and computational studies of N-(3-(-2-(7-Chloroquinolin-2-yl)vinyl) benzylidene)anilines as fungal biofilm inhibitors

Cited by 13 publications

References 37 publications

Bacterial virulence factors: a target for heterocyclic compounds to combat bacterial resistance

Bacterial virulence factors: a target for heterocyclic compounds to combat bacterial resistance

Strategies and Approaches for Discovery of Small Molecule Disruptors of Biofilm Physiology

Recent update on antibacterial and antifungal activity of quinoline scaffolds

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