Synthesis and Biological Evaluation of New 1,2,3‐Triazolyl‐Pyrazolyl‐Quinoline Derivatives as Potential Antimicrobial Agents

Thakare, Prashant P.; Shinde, Abhijit; Chavan, Abhijit P.; Nyayanit, Narendra V.; Bobade, Vivek D.; Mhaske, Pravin C.

doi:10.1002/slct.201904455

Cited by 25 publications

(21 citation statements)

References 55 publications

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“…The synthetic path for 4‐(4‐(1‐benzyl‐1H‐1,2,3‐triazol‐4‐yl)‐1‐phenyl‐1H‐pyrazol‐3‐yl)quinoline 6a‐t is shown in Scheme 1. 1‐(Quinolin‐4‐yl)ethanone [ 53 ] 1a‐d upon condensation with phenyl hydrazine followed by a formylation with DMF/POCl 3 gave 1‐phenyl‐3‐(quinolin‐4‐yl)‐1 H ‐pyrazole‐4‐carbaldehyde 2a‐d . [ 54 ] Aldehyde 2a‐d upon reaction with dimethyl(1‐diazo‐2‐oxopropyl)phosphonate (Bestmann‐Ohira reagent) in methanol gave 4‐(4‐ethynyl‐1‐phenyl‐1 H ‐pyrazol‐3‐yl)quinoline 4a‐d .…”

Section: Resultsmentioning

confidence: 99%

Synthesis and antimycobacterial screening of new 4‐(4‐(1‐benzyl‐1H‐1,2,3‐triazol‐4‐yl)‐1‐phenyl‐1H‐pyrazol‐3‐yl)quinoline derivatives

Thakare

Walunj

Chavan

et al. 2020

Journal of Heterocyclic Chem

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A new series of 4‐(4‐(1‐benzyl‐1H‐1,2,3‐triazol‐4‐yl)‐1‐phenyl‐1H‐pyrazol‐3‐yl)quinoline (6a‐t) have been synthesized by a click reaction of 4‐(4‐ethynyl‐1‐phenyl‐1H‐pyrazol‐3‐yl)quinoline (4a‐d) with a substituted benzyl azide (5a‐e). The starting alkyne derivatives 4a‐d are obtained from Bestmann‐Ohira reaction of 1‐phenyl‐3‐(quinolin‐4‐yl)‐1H‐pyrazole‐4‐carbaldehyde and dimethyl(1‐diazo‐2‐oxopropyl)phosphonate. The newly synthesized compounds are screened against M. tuberculosis H37Ra dormant and active, Escherichia coli, Pseudomonas fluorescence, Staphylococcus aureus and Bacillus subtilis strains at 30 μg/mL concentration. Most of the screened compounds showed good to moderate antibacterial activity against S. aureus, B. subtilis, and Mycobacterium tuberculosis H37Ra strains. The synthesized derivatives of quinolinyl‐pyrazole‐4‐carbaldehyde and quinolinyl‐pyrazole‐4‐ethyne reportd good to moderate activity against both strains of M. tuberculosis H37Ra. Ten derivatives of quinolinyl‐pyrazole presented good activity against B. subtilis. These results suggested that further optimization and development of quinolinyl‐pyrazolyl‐1,2,3‐triazole moeity could serve as lead compounds for antimycobacterial activity.

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Section: Resultsmentioning

confidence: 99%

Synthesis and antimycobacterial screening of new 4‐(4‐(1‐benzyl‐1H‐1,2,3‐triazol‐4‐yl)‐1‐phenyl‐1H‐pyrazol‐3‐yl)quinoline derivatives

Thakare

Walunj

Chavan

et al. 2020

Journal of Heterocyclic Chem

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“…In Gram-positive bacteria, the most effective com- showed quite close antibacterial efficiency against Bacillus subtilis compared with streptomycin. [33] Candida albicans is the most pathogenic species that is a part of normal human flora. The most effective compounds on Candida albicans are 3 e, 3 a, 3 b, 5 d, and 4 b.…”

Section: Antimicrobial Activitymentioning

confidence: 99%

Adenine Derivatives for Regenerable Antibacterial Surface Applications Based on A−T Base Pairing

et al. 2020

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Surface contamination is a major concern in the design, fabrication, and application of biomaterials. In this work, a series of new adenine derivatives were synthesized in a three‐step method with the goal of protecting the functional materials against microbial adhesion. Initially, 9‐(chloroalkyl)‐9H‐purin‐6‐amine compounds were synthesized from adenine. Then, these compounds were reacted with potassium thiocyanate or potassium selenocyanate. In the last step, adenine derivatives incorporating a tetrazole ring were synthesized via the cycloaddition of sodium azide with thiocyano or selenocyano derivatives. The antimicrobial activity of the compounds was evaluated by using the minimal inhibitory concentration method. Furthermore, the effect of the compounds on pBR322 plasmid DNA was studied using gel electrophoretic mobility measurements. The antimicrobial assay showed that some of the synthesized compounds exerted vigorous antibacterial and antifungal activities. Further experiments indicated that seleno‐adenine derivatives have higher antimicrobial and DNA effect than other derivatives. The surfaces activated by the adenine derivative demonstrated antibacterial activity resisting bacterial attachment in order to remove dead bacteria from the surface. All results showed that some of these adenine derivatives have an antibacterial activity and the potential for further applications, for example as a smart surface coating that prevents bacterial adhesion to biomaterials.

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“…Among N ‐containing heterocycles, the quinoline nucleus was found in nature, and many biologically active derivatives were extensively explored in different therapeutic areas such as antimalarial, [ 7 ] antibacterial, [ 8 ] antifungal, [ 9 ] anti‐inflammatory, [ 10 ] antimicrobial, [ 11 ] and antituberculosis. [ 12 ] Quinoline derivatives isolated from natural products also exhibited substantial antitubercular activity.…”

Section: Introductionmentioning

confidence: 99%

Quinoline‐Proline, Triazole Hybrids: Design, Synthesis, Antituberculosis, Molecular Docking, and ADMET Studies

Ganesan¹,

Raja²,

Murugesan

et al. 2021

Journal of Heterocyclic Chem

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A series of novel quinoline‐proline hybrids (11a‐g) and quinoline‐proline‐1,2,3‐triazole hybrids (12‐14) were synthesized by click chemistry based on molecular hybridization concept and were characterized by NMR, mass spectrometry, and elemental analysis. All the titled target compounds were tested for antitubercular activity by MABA and LORA methods by in vitro. Interestingly, two compounds (2R,4S)‐1‐((2‐cyclopropyl‐4‐(4‐fluorophenyl)‐quinolin‐3‐yl)‐methyl)‐4‐(4‐nitrobenzamido)‐N‐phenylpyrrolidine‐2‐carboxamide (11b) and (2R,4S)‐1‐((2‐cyclopropyl‐4‐(4‐fluorophenyl)‐quinolin‐3‐yl)‐methyl)‐4‐(4‐fluorobenzamido)‐N‐phenylpyrrolidine‐2‐carboxamide (11c) exhibited significant activity against the tested Mycobacterium tuberculosis H37Rv strain. Further, the cytotoxicity (CC50) profile of the titled compounds against the Vero cell was performed and discussed. A molecular docking study of the hit compounds (11b and 11c) was also performed to find their putative binding interaction with the active site of the target proteins. Finally, in silico ADMET properties were also predicted for all the synthesized molecules to evaluate their drug‐likeness behavior.

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Synthesis and Biological Evaluation of New 1,2,3‐Triazolyl‐Pyrazolyl‐Quinoline Derivatives as Potential Antimicrobial Agents

Cited by 25 publications

References 55 publications

Synthesis and antimycobacterial screening of new 4‐(4‐(1‐benzyl‐1H‐1,2,3‐triazol‐4‐yl)‐1‐phenyl‐1H‐pyrazol‐3‐yl)quinoline derivatives

Synthesis and antimycobacterial screening of new 4‐(4‐(1‐benzyl‐1H‐1,2,3‐triazol‐4‐yl)‐1‐phenyl‐1H‐pyrazol‐3‐yl)quinoline derivatives

Adenine Derivatives for Regenerable Antibacterial Surface Applications Based on A−T Base Pairing

Quinoline‐Proline, Triazole Hybrids: Design, Synthesis, Antituberculosis, Molecular Docking, and ADMET Studies

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