Synthesis, characterization, antibacterial, antioxidant, DNA binding and SAR study of a novel pyrazine moiety bearing 2-pyrazoline derivatives

Kitawat, Bheru Singh; Singh, Man

doi:10.1039/c4nj00594e

Cited by 23 publications

(15 citation statements)

References 42 publications

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“…Many studies have been reported on the formation of ( 2d ) under ethanolic base conditions 34,35 . However, attempted synthesis of 1H‐pyrazoline ( 2d ) was not availed due to the reversible reaction 34 . The presence of free proton in 2d is believed to form interaction with carboxylic group, which eventually retard the formation of pyrazoline.…”

Section: Resultsmentioning

confidence: 99%

Microwave‐assisted Synthesis and Molecular Docking Study of Heteroaromatic Chalcone Derivatives as Potential Antibacterial Agents

Farooq

Ngaini

Mortadza

2020

Bulletin Korean Chem Soc

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In this study, a series of chalcone derivatives (1a-c) were synthesized via Claisen-Schmidt condensation, followed by aza-Michael addition to form pyrazoline derivatives (2a-c and 3a-c). The reaction was performed via microwave radiation to give excellent yields (77-93%) in 1-3.5 min. Microwave-assisted reaction of Fischer esterification of pyrazolines (2a-c and 3a-c) afforded heteroaromatic pyrazoline esters (4a-c) in high yield (83-96% in <2 min) compared to conventional reflux (55-79% in 30 min). Compounds 1a-c and 3a-c demonstrated excellent antibacterial activity against Staphylococcus aureus via disc diffusion assay with inhibition zone with 13 and 19 mm compared to a standard drug, ampicillin (11 mm). Structure activity relationship of 1b and 3b were visualized via molecular docking interaction against 4pql protein of S. aureus with binding free energy −7.0 and −8.0 kcal/mol, respectively. This study is significant in drug discovery process particularly for pharmaceutical industries.

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Section: Resultsmentioning

confidence: 99%

Microwave‐assisted Synthesis and Molecular Docking Study of Heteroaromatic Chalcone Derivatives as Potential Antibacterial Agents

Farooq

Ngaini

Mortadza

2020

Bulletin Korean Chem Soc

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“…The pyrazoline derivatives P1 – P18 were synthesized according to the protocol outlined in Scheme 1 and Scheme 2, using a synthetic approach via chalcone. This strategy has been extensively used in the past by our and other research groups, in order to obtain 1,3,5-substituted pyrazolines [11,19,20,21,22]. The first reaction of this multi-step procedure was the synthesis of para -substituted acetophenones (Scheme 1, I ).…”

Section: Resultsmentioning

confidence: 99%

Design, Synthesis, Docking Studies and Monoamine Oxidase Inhibition of a Small Library of 1-acetyl- and 1-thiocarbamoyl-3,5-diphenyl-4,5-dihydro-(1H)-pyrazoles

et al. 2019

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New N-acetyl/N-thiocarbamoylpyrazoline derivatives were designed and synthesized in high yields to assess their inhibitory activity and selectivity against human monoamine oxidase A and B. The most important chiral compounds were separated into their single enantiomers and tested. The impact of the substituents at N1, C3 and C5 positions as well the influence of the configuration of the C5 on the biological activity were analyzed. Bulky aromatic groups at C5 were not tolerated. p-Prenyloxyaryl moiety at C3 oriented the selectivity toward the B isoform. The results were also corroborated by molecular modelling studies providing new suggestions for the synthesis of privileged structures to serve as lead compounds for the treatment of mood disorders and neurodegenerative diseases.

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“…[6] The unsaturated α,βketo moiety in the chalcone network is also very reactive for the formation of heterocyclic organic chalcone derivatives such as pyrimidine, [10] epoxy chalcone, [11] pyrazoline. [12] Pyrazoline is an eye catching heterocyclic molecule due to the presence of heteroatom nitrogen in cyclic ring, which played marvelous role in the field of medicines (i. e. antiepileptic, [13] antitrypanosomal, [14] antipyretic, [15,16] antioxidant, [17] anti-inflammatory, [18] antimalarial, [19] antihistaminic [20] ) and electronics (e. g. photographic conductor, [21] chemo-sensor [22] and optoelectronic [23] ). [24] Pyrazoline derivatives were commonly derived via aza-Michael addition reaction of hydrazine and chalcone derivatives under versatile conditions.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Molecular Docking and Antimicrobial Activity of α, β‐Unsaturated Ketone Exchange Moiety for Chalcone and Pyrazoline Derivatives

Farooq

Ngaini

2020

ChemistrySelect

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Bacterial diseases cause hazardous infections due to the occurrence of bacterial resistance. Drugs production to cure bacterial resistance from natural sources has become ineffective to execute the resisted bacteria due to the unsuitable binding interaction of active sites with the receptors. Drug link to natural products moieties such as chalcones and pyrazolines, which originated from plants extracts, has become attractive among researchers due to its significant pharmaceutical moiety. In this study a series of chalcone derivatives (1 a–d) has been synthesized via Claisen‐Schmidt condensation, followed by cyclization to form pyrazolines (2 a–d, 3 a–d). Fischer esterification of pyrazolines formed 4 a–d in moderate to good yield (42.91‐88.23 %). Antimicrobial activities of all the synthesized compounds were evaluated against Escherichia coli and Staphylococcus aureus via disc diffusion. Among all compounds, pyrazolines 3 c and 3 d showed the highest zone of inhibition (17 mm) compared to 1 a‐d (5‐11 mm) and standard ampicillin (11 mm). The exchange of α, β‐unsaturated carbonyl showed phenomenal increment in the biological activities. Structure activity relationship of 1 a, 1 d, 3 a and 3 d was analyzed via molecular docking of N‐terminal domain having deoxyribonucleic acid (DNA) binding protein (4pql) with excellent binding energy of −6.2, −6.6, −7.1 and −7.2 kcal/mol, respectively. This work is significant in designing new drugs with keto‐exchange relationship for medicinal industry.

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Synthesis, characterization, antibacterial, antioxidant, DNA binding and SAR study of a novel pyrazine moiety bearing 2-pyrazoline derivatives

Cited by 23 publications

References 42 publications

Microwave‐assisted Synthesis and Molecular Docking Study of Heteroaromatic Chalcone Derivatives as Potential Antibacterial Agents

Microwave‐assisted Synthesis and Molecular Docking Study of Heteroaromatic Chalcone Derivatives as Potential Antibacterial Agents

Design, Synthesis, Docking Studies and Monoamine Oxidase Inhibition of a Small Library of 1-acetyl- and 1-thiocarbamoyl-3,5-diphenyl-4,5-dihydro-(1H)-pyrazoles

Synthesis, Molecular Docking and Antimicrobial Activity of α, β‐Unsaturated Ketone Exchange Moiety for Chalcone and Pyrazoline Derivatives

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