One-Pot and Two-Pot Synthesis of Chalcone Based Mono and Bis-Pyrazolines

Farooq, Saba; Ngaini, Zainab

doi:10.1016/j.tetlet.2019.151416

Cited by 46 publications

(38 citation statements)

References 117 publications

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“…In the recent years, a number of review articles for-or including-pyrazolines have been published. They are concerned with the structure, with emphasis on the synthetic strategies [6,7], with their biological activities in general [8][9][10][11], or they even focus on their interesting photophysical properties [12]. In fact, a few of them include pyrazoline as a substructure of pyrazole.…”

Section: Introduction Overview and Classificationmentioning

confidence: 99%

Pyrazoline Hybrids as Promising Anticancer Agents: An Up-to-Date Overview

Matiadis

Sagnou

2020

IJMS

104

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Pyrazolines are five-membered heterocycles possessing two adjacent nitrogens. They have attracted significant attention from organic and medicinal chemists due to their potent biological activities and the numerous possibilities for structural diversification. In the last decade, they have been intensively studied as targets for potential anticancer therapeutics, producing a steady yearly rise in the number of published research articles. Many pyrazoline derivatives have shown remarkable cytotoxic activities in the form of heterocyclic or non-heterocyclic based hybrids, such as with coumarins, triazoles, and steroids. The enormous amount of related literature in the last 5 years prompted us to collect all these published data from screening against cancer cell lines, or protein targets like EGFR and structure activity relationship studies. Therefore, in the present review, a comprehensive account of the compounds containing the pyrazoline nucleus will be provided. The chemical groups and the structural modifications responsible for the activity will be highlighted. Moreover, emphasis will be given on recent examples from the literature and on the work of research groups that have played a key role in the development of this field.

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Section: Introduction Overview and Classificationmentioning

confidence: 99%

Pyrazoline Hybrids as Promising Anticancer Agents: An Up-to-Date Overview

Matiadis

Sagnou

2020

IJMS

104

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“…Chalcone is a stable intermediate 2 for the synthesis of various heterocyclic compounds such as isoxazole, 3 pyrazoline, 4 epoxide, 5 thiazine, 6 indazole, 7 and pyrimidine 8 valuable in pharmaceutical industries 9 . A recent study disclosed a series of heterocyclic chalcones especially pyrazoline 10 derivatives with remarkable biological properties such as antioxidant, 11 antibacterial, 12 antidepressant, 13 anticancer, 14 antipyretic, 15 antimalarial, 16 antitubercular 17 as well as non‐biological applications in solar dyes, chemosensors, 18 photo‐conductors, 19 and optoelectronic devices 20 . Pyrazolines are well known heterocyclic compounds with aromaticity.…”

Section: Introductionmentioning

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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“…[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. [25] Structural modifications or improvement in pyrazoline has contributed to the discovery of new drugs with less toxicity and improved potency.…”

Section: Introductionmentioning

confidence: 99%

“…[28] The position of double bond in the pyrazoline network has also contributed to the biological activity of the compounds. [24] Antimicrobial activity and interaction between drugs and their molecular targets are significant for treatment of pathogenic microbial infections (i. e. malaria, cough, tuberculosis, plague). [29] The drug interactions can significantly reduce the resistance of microbes.…”

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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One-Pot and Two-Pot Synthesis of Chalcone Based Mono and Bis-Pyrazolines

Cited by 46 publications

References 117 publications

Pyrazoline Hybrids as Promising Anticancer Agents: An Up-to-Date Overview

Pyrazoline Hybrids as Promising Anticancer Agents: An Up-to-Date Overview

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

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

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