Synthesis and biological evaluation of 2-phenyl-4-aminoquinolines as potential antifungal agents

Yang, Rui; Du, Wei; Yuan, Huatang; Qin, Tianhong; He, Renxiao; Ma, Yan; Du, Haiying

doi:10.1007/s11030-019-10012-1

Cited by 14 publications

(13 citation statements)

References 33 publications

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“…The preparation of target compounds has been accomplished in four steps ( Scheme 1) according to similar procedures described previously [30] . Firstly, the amides 3a – 3o were obtained from ammonolysis of the corresponding acyl chlorides 2a – 2o with 1‐(6‐amino‐2 H ‐1,3‐benzodioxol‐5‐yl)ethan‐1‐one ( 1 ) in the presence of triethylamine in good to excellent yields.…”

Section: Resultsmentioning

confidence: 99%

“…As described in Table 1, all the target compounds ( 6a – 6j and 7a – 7n ), as well as the positive control azoxystrobin (a commercial agricultural fungicide), were screened in vitro for their antifungal activities against five phytopathogenic fungi ( P. piricola , A. brassicae , C. lunata , P. grisea and A. alternate ) at 50 μg/mL by using mycelium growth rate method [14,30] . The results revealed that most of the newly synthesized compounds exhibited moderate to excellent inhibitory activities at the concentration of 50 μg/mL, and many of them displayed comparable or more superior antifungal profiles compared with the positive control, particularly for A. brassicae , C. lunata and A. alternate .…”

Section: Resultsmentioning

confidence: 99%

“…All title compounds were evaluated for their antifungal activities against five phytopathogenic fungi ( Physalospora piricola , Alternaria brassicae , Curvularia lunata , Pyricularia grisea and Alternaria alternate ) by using mycelium growth rate method as reported previously [14,30] . Azoxystrobin, a commercial agricultural fungicide, was used as the positive control.…”

Section: Methodsmentioning

confidence: 99%

“…Previous studies of our working group investigated some 2,4‐disubstituted quinolines as potential antifungal agents [14,30] . It was found that quinoline derivatives with a phenyl substitution at position 2 and an aniline moiety at position 4 were potent antifungal candidates and the aniline moiety at position 4 played a key role in antifungal potency, which were of great value for further study.…”

Section: Introductionmentioning

confidence: 98%

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4‐Aminoquinolines Bearing a 1,3‐Benzodioxole Moiety: Synthesis and Biological Evaluation as Potential Antifungal Agents

Yang

Xie

et al. 2021

Chemistry & Biodiversity

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In search of new environmentally friendly and effective antifungal agents, a series of 4‐aminoquinolines bearing a 1,3‐benzodioxole moiety were prepared and their structures were fully elucidated by spectroscopic analyses. The antifungal activities of all the target compounds against five phytopathogenic fungi were evaluated in vitro. The results revealed that most of the newly synthesized compounds exhibited obvious inhibitory activities at the concentration of 50 μg/mL. Among them, 6‐(furan‐2‐yl)‐N‐(4‐methylphenyl)‐2H‐[1,3]dioxolo[4,5‐g]quinolin‐8‐amine hydrochloride (7m) displayed more promising antifungal potency with EC50 values of 10.3 and 14.0 μg/mL against C. lunata and A. alternate, respectively. Particularly, the EC50 value of 7m against C. lunata was 7.3‐fold as potent as the standard azoxystrobin. There were some significant morphological alterations in the mycelia of C. lunata when treated with 7m at 50 μg/mL. Additionally, the preliminary structure–activity relationships (SARs) were also discussed. Thus, this study suggests that 4‐aminoquinolines bearing a 1,3‐benzodioxole moiety are interesting scaffolds for the development of novel antifungal agents.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 98%

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4‐Aminoquinolines Bearing a 1,3‐Benzodioxole Moiety: Synthesis and Biological Evaluation as Potential Antifungal Agents

Yang

Xie

et al. 2021

Chemistry & Biodiversity

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“…Diverse secondary amines at 2‐phenylquinoline 4‐position resulted in the 4‐aminoquinoline set of molecules. [ 58 ] Compared with azoxystrobin, moderate‐to‐excellent antifungal effects are noticed. However, only a few derivatives are successful in exhibiting strong antifungal properties, wherein quinoline analog 99 (Figure 16) with 4‐chloroaniline moiety has exhibited 5.6‐fold higher Cochliobolus lunata inhibitory potency (MIC = 13.3 µg/ml) than azoxystrobin (EC 50 = 75.0 µg/ml), whereas 2.4‐ and 1.02‐fold stronger antifungal activity against Pyricularia grisea (EC 50 = 15.6 µg/ml) and Alternaria alternata (EC 50 = 14.4 µg/ml), respectively.…”

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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Accessing 2‐Aryl Quinolines via Acceptorless Dehydrogenation and Transfer Hydrogenation Under Base and Solvent‐Free Reaction Conditions

M.,

P.,

et al. 2023

ChemistrySelect

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Catalytic hydrogenation/dehydrogenation reactions are one of the most active areas of research for the synthesis of pharmaceuticals and fine chemicals. Despite several efficient homogeneous catalysts that have already been identified, highly active heterogeneous catalysts remain elusive. Herein, we report an easy and convenient wet impregnation method for the synthesis of Pd‐nanoclusters supported on ZnO nanoparticles. The catalyst displays a multifunctional role in 2‐aryl quinolines synthesis using alcohol and 2‐nitrobenzyl alcohol as reactants via dehydrogenation/hydrogenation pathway under neat and base‐free reaction conditions. The catalyst exhibits excellent selectivity and can be recycled five times without appreciable loss in its activity.

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Synthesis and biological evaluation of 2-phenyl-4-aminoquinolines as potential antifungal agents

Cited by 14 publications

References 33 publications

4‐Aminoquinolines Bearing a 1,3‐Benzodioxole Moiety: Synthesis and Biological Evaluation as Potential Antifungal Agents

4‐Aminoquinolines Bearing a 1,3‐Benzodioxole Moiety: Synthesis and Biological Evaluation as Potential Antifungal Agents

Recent update on antibacterial and antifungal activity of quinoline scaffolds

Accessing 2‐Aryl Quinolines via Acceptorless Dehydrogenation and Transfer Hydrogenation Under Base and Solvent‐Free Reaction Conditions

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