A simple and efficient microwave assisted synthesis of pyrrolidinyl-quinoline based pyrazoline derivatives and their antimicrobial activity

Pradeep, M.; Vishnuvardhan, M.V.P.S.; Thalari, Gangadhar

doi:10.1016/j.cdc.2021.100666

Cited by 11 publications

(6 citation statements)

References 15 publications

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“…Good activity against fungi was shown by compounds 26 e(R = 3,4-Dimethoxy), 26 f(4-fluoro), 26 h(2-Bromo), 26 j(R = 2-Nitro), 26 k(2-thienyl), 26 l(3-Pyridyll). [24] (Scheme 4) Rajendran Satheeshkumar et al developed a novel method to synthesise polycyclic quinoline derivatives by SSA (Silica sulphuric acid) catalysed Friedlander reaction. Condensation reaction was carried out for 2-aminoarylketones (27) with either 1,2-cyclohexanedione (28) or 1,3-cyclohexanedione (30) to prepare 2,3-dihydroacridin-4-ones (29) and 3,4-dihydroacridin-1-ones (31).…”

Section: Chemistryselectmentioning

confidence: 99%

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Chemistry of Quinoline Based Heterocycle Scaffolds: A Comprehensive Review

et al. 2022

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Quinoline is a significant scaffold among heterocyclic compounds and can be used as a key building block for the development of novel medications. Quinoline and its derivatives are recognised as biologically active substances with a number of pharmacological properties. Nowadays, quinolinebased heterocycle scaffolds have achieved a prominent position in medicinal chemistry due to their significant pharmaco-logical and biological properties. The discovery and creation of cutting-edge medications to treat a variety of diseases is an example of the usefulness of these compounds. The current study outlines the range of methods available to create different quinolone-based heterocycle scaffolds and their advantageous therapeutic applications using the literature that has been published up to 2022.

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Section: Chemistryselectmentioning

confidence: 99%

“…Cup plate agar method was used by measuring inhibition zone in mm at concentration of 500 μg/ml by using DMSO. Good activity against fungi was shown by compounds 26 e(R=3,4‐Dimethoxy) , 26 f(4‐fluoro) , 26 h(2‐Bromo), 26 j(R=2‐Nitro) , 26 k(2‐thienyl) , 26 l(3‐Pyridyll) [24] . (Scheme 4)…”

Section: Introductionmentioning

confidence: 99%

Chemistry of Quinoline Based Heterocycle Scaffolds: A Comprehensive Review

et al. 2022

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“…In 2021, Pradeep et al used sodium acetate as a base catalyst for synthesis of 2‐pyrazolines [39] . Firstly, they studied the reaction between pyrrolidinyl‐quinoline chalcone 18 a and hydrazine hydrate 18 b as a model reaction and investigated the 2‐pyrazolines 18c yield in various conditions (Scheme 18).…”

Section: Synthetic Strategiesmentioning

confidence: 99%

“…This MWI‐assisted approach was utilized for synthesis of 2‐pyrazolines 19 c from pyrrolidinyl‐quinoline chalcones 19 a and hydrazine hydrate 19 b and was compared with conventional heating methods in terms of yield and reaction time (Scheme 19). [39] …”

Section: Synthetic Strategiesmentioning

confidence: 99%

Synthesis of 2‐Pyrazolines from Hydrazines: Mechanisms Explained

et al. 2021

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2-Pyrazoline core is a very interesting five-membered heterocycle, which has been explored in recent years due to its vast applications as the core structure of bioactive and industrial agents. Based on literature studies, versatile synthetic approaches have been employed for the preparation of 2pyrazolines, among them the reaction between hydrazines and α,β-unsaturated enones as the most used method. In this review article, different methods for the synthesis of 2-pyrazolines using hydrazine derivatives were classified and presented.Initially, numerous catalytic methods for the preparation of 2pyrazolines from hydrazines and α,β-unsaturated enones are reviewed and various aspects of these methods discussed including catalyst efficiency, catalyst recovery, green chemistry, cost-effectiveness, scope of the method, enantioselectivity, and yield. In addition, reactions between hydrazines and other reagents in multicomponent and two-component reactions, developed recently, are discussed. Finally, some of the important applications of 2-pyrazolines are summarized.

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“…Compounds incorporating quinoline-based bioactive heterocycles such as pyrrole, pyrazoline, or benzopyrrole rings have drawn considerable attention with pronounced antimicrobial effect. − These compounds were utilized as broad spectrum antibiotic drugs that work on both Gram-positive and Gram-negative pathogens as well as many fungal strains. − The antimicrobial effect of these classes of compounds is mediated through different mechanisms. They have reported to act as inhibitors of DNA gyrase, topoisomerase, and as urease inhibitors. ,, …”

Section: Introductionmentioning

confidence: 99%

Design and Synthesis of 2-(4-Bromophenyl)Quinoline-4-Carbohydrazide Derivatives via Molecular Hybridization as Novel Microbial DNA-Gyrase Inhibitors

et al. 2023

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Microbial DNA gyrase is regarded as an outstanding microbial target. Hence, 15 new quinoline derivatives (5–14) were designed and synthesized. The antimicrobial activity of the afforded compounds was pursued via in vitro approaches. The investigated compounds displayed eligible MIC values, particularly against G-positive Staphylococcus aureus species. Consequently, an S. aureus DNA gyrase supercoiling assay was performed, using ciprofloxacin as a reference control. Obviously, compounds 6b and 10 unveiled IC50 values of 33.64 and 8.45 μM, respectively. Alongside, ciprofloxacin exhibited an IC50 value of 3.80 μM. Furthermore, a significant docking binding score was encountered by compound 6b (−7.73 kcal/mol), surpassing ciprofloxacin (−7.29 kcal/mol). Additionally, both compounds 6b and 10 revealed high GIT absorption without passing the blood brain barrier. Finally, the conducted structure−activity relationship study assured the usefulness of the hydrazine moiety as a molecular hybrid for activity either in cyclic or opened form.

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A simple and efficient microwave assisted synthesis of pyrrolidinyl-quinoline based pyrazoline derivatives and their antimicrobial activity

Cited by 11 publications

References 15 publications

Chemistry of Quinoline Based Heterocycle Scaffolds: A Comprehensive Review

Chemistry of Quinoline Based Heterocycle Scaffolds: A Comprehensive Review

Synthesis of 2‐Pyrazolines from Hydrazines: Mechanisms Explained

Design and Synthesis of 2-(4-Bromophenyl)Quinoline-4-Carbohydrazide Derivatives via Molecular Hybridization as Novel Microbial DNA-Gyrase Inhibitors

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