Synthesis, QSAR and anticandidal evaluation of 1,2,3-triazoles derived from naturally bioactive scaffolds

Irfan, Mohammad; Aneja, Babita; Yadava, Umesh; Khan, Shabana; Manzoor, Nikhat; Daniliuc, Constantin G.; Abid, Mohammad

doi:10.1016/j.ejmech.2015.02.007

Cited by 68 publications

(43 citation statements)

References 23 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…tropicalis , respectively. This enhanced anticandidal activity of compound 3a may be due to the presence of quinoline ring along with 1,2,3 triazole ring in its structure [20]. To determine the role of N -atom present in the quinoline ring and the effect of substitution on quinoline ring, we synthesized two new structural analogues ( 3b and 3c ).…”

Section: Resultsmentioning

confidence: 99%

“…The crude product was purified by column chromatography with petroleum ether: ethyl acetate (8:2) to give the desired alkynes ( 2a-c ) in good to excellent yields. The synthesis of compound 2a [ 8-(Prop-2-ynyloxy)quinoline] has been previously reported in our lab [20]. …”

Section: Methodsmentioning

confidence: 99%

“…The crude was purified by column chromatography using dichloromethane and methanol (9:1) as eluent to give 1,2,3-triazole derivatives in good to excellent yields. The compound 3a [1-Benzyl-4-(quinolin-1-yloxy)methyl)-1H-1,2,3-triazole] has been previously reported in our lab [20]. …”

Section: Methodsmentioning

confidence: 99%

“…In our previous study, we synthesized a series of novel 1,2,3-triazole derivatives from naturally bioactive alcohols and evaluated their anti- Candida activity as well as cytotoxicity [20]. The results showed that quinoline containing 1,2,3-triazole ( 3a ) has great potential to inhibit the Candida spp in vitro .…”

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Effect of quinoline based 1,2,3-triazole and its structural analogues on growth and virulence attributes of Candida albicans

et al. 2017

Self Cite

View full text Add to dashboard Cite

Candida albicans, along with some other non-albicans Candida species, is a group of yeast, which causes serious infections in humans that can be both systemic and superficial. Despite the fact that extensive efforts have been put into the discovery of novel antifungal agents, the frequency of these fungal infections has increased drastically worldwide. In our quest for the discovery of novel antifungal compounds, we had previously synthesized and screened quinoline containing 1,2,3-triazole (3a) as a potent Candida spp inhibitor. In the present study, two structural analogues of 3a (3b and 3c) have been synthesized to determine the role of quinoline and their anti-Candida activities have been evaluated. Preliminary results helped us to determine 3a and 3b as lead inhibitors. The IC50 values of compound 3a for C. albicans ATCC 90028 (standard) and C. albicans (fluconazole resistant) strains were 0.044 and 2.3 μg/ml, respectively while compound 3b gave 25.4 and 32.8 μg/ml values for the same strains. Disk diffusion, growth and time kill curve assays showed significant inhibition of C. albicans in the presence of compounds 3a and 3b. Moreover, 3a showed fungicidal nature while 3b was fungistatic. Both the test compounds significantly lower the secretion of proteinases and phospholipases. While, 3a inhibited proteinase secretion in C. albicans (resistant strain) by 45%, 3b reduced phospholipase secretion by 68% in C. albicans ATCC90028 at their respective MIC values. Proton extrusion and intracellular pH measurement studies suggested that both compounds potentially inhibit the activity of H+ ATPase, a membrane protein that is crucial for various cell functions. Similarly, 95–97% reduction in ergosterol content was measured in the presence of the test compounds at MIC and MIC/2. The study led to identification of two quinoline based potent inhibitors of C. albicans for further structural optimization and pharmacological investigation.

show abstract

Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Effect of quinoline based 1,2,3-triazole and its structural analogues on growth and virulence attributes of Candida albicans

et al. 2017

Self Cite

View full text Add to dashboard Cite

show abstract

“…Therefore, it has lent additional urgency to develop new molecular scaffolds having novel mode of action or to modify existing drug molecules. Considering the large pharmacological importance of b-lactams and in extension to our efforts to explore novel biologically active molecules 19,20 , we synthesized novel N-benzyl-3,4-diaryl substituted 2-azitidinone (b-lactam) derivatives (4a-g, 4i-s), while compounds 4h and 4t were isolated as highly substituted 1,3-oxazin-4-one derivatives. In silico pharmacokinetic and toxicity parameters were also assessed for all the synthesized compounds.…”

Section: Introductionmentioning

confidence: 99%

Monocyclicβ-lactam and unexpected oxazinone formation: synthesis, crystal structure, docking studies and antibacterial evaluation

Aneja

Irfan

Hassan

et al. 2015

Journal of Enzyme Inhibition and Medicinal Chemistry

Self Cite

View full text Add to dashboard Cite

Novel monocyclic b-lactam derivatives bearing aryl, phenyl and heterocyclic rings were synthesized as possible antibacterial agents. Cyclization of imines (3h, 3t) with phenylacetic acid in the presence of phosphoryl chloride and triethyl amine did not afford the expected b-lactams. Instead, highly substituted 1,3-oxazin-4-ones (4h, 4t) were isolated as the only product and confirmed by single crystal X-ray analysis of 4t. The results of antibacterial activity showed that compound 4l exhibited considerable antibacterial activity with MIC and MBC values of 62.5 mg/mL against Klebsiella pneumoniae. Cytotoxicity assay on Chinese Hamster Ovary (CHO) cell line revealed non-cytotoxic behavior of compounds 4d, 4h, 4k and 4l up to 200 mg/mL conc. Molecular docking was performed for compound 4l with penicillin binding protein-5 to identify the nature of interactions. The results of both in silico and in vitro evaluation provide the basis for compound 4l to be carried as a potential lead molecule in the drug discovery pipeline against bacterial infections.

show abstract

Grafting Nature‐Inspired and Bio‐Based Phenolic Esters onto Cellulose Nanocrystals Gives Biomaterials with Photostable Anti‐UV Properties

et al. 2020

View full text Add to dashboard Cite

New nature‐inspired and plant‐derived p‐hydroxycinnamate esters and p‐hydroxycinnamate diesters provide excellent protection against UV radiation when incorporated into a matrix. Herein, an efficient and sustainable pathway is reported to graft these phenolic compounds onto cellulose nanocrystals (CNCs) via click‐type copper‐catalyzed azide/alkyne cycloaddition (CuAAC) reaction. The successful grafting of the phenolic esters on CNC surface was evidenced by a range of chemical analyses, and the degrees of substitution (DS) of the CNC were found to depend on the structure of the phenolic ester grafted. Moreover, aqueous suspensions of the phenolic ester‐grafted CNCs not only strongly absorb in both the UVA and UVB regions, but they also exhibit average to very high photostability. Their wide spectrum UV‐absorbing properties and their stability upon exposure to UV are highly influenced by the structure of the phenolic ester, particularly by the extra ester group in p‐hydroxycinnamate diesters. These findings demonstrate that cellulose nanocrystals decorated with such plant‐derived and nature‐inspired phenolic esters are promising sustainable nanomaterials for anti‐UV applications.

show abstract

Synthesis, QSAR and anticandidal evaluation of 1,2,3-triazoles derived from naturally bioactive scaffolds

Cited by 68 publications

References 23 publications

Effect of quinoline based 1,2,3-triazole and its structural analogues on growth and virulence attributes of Candida albicans

Effect of quinoline based 1,2,3-triazole and its structural analogues on growth and virulence attributes of Candida albicans

Monocyclicβ-lactam and unexpected oxazinone formation: synthesis, crystal structure, docking studies and antibacterial evaluation

Grafting Nature‐Inspired and Bio‐Based Phenolic Esters onto Cellulose Nanocrystals Gives Biomaterials with Photostable Anti‐UV Properties

Contact Info

Product

Resources

About