Green synthesis of coumarin-pyrazolone hybrids: In vitro anticancer and anti-inflammatory activities and their computational study on COX-2 enzyme

Kulkarni, Rashmi C.; Madar, Jyoti M.; Shastri, Samundeeswari L.; Shaikh, Farzanabi; Naik, Nirmala S.; Chougale, Ravindra B.; Joshi, Shrinivas D.; Dixit, Sheshagiri R.; Sunagar, Vinay A.

doi:10.1016/j.cdc.2018.11.004

Cited by 10 publications

(7 citation statements)

References 23 publications

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“…Further, the work was extended for the development of better inhibition at low concentration, and novel coumarin was synthesized using different hybrids. Kulkarni et al 133 reported a sequence of new coumarin-pyrazolone hybrids by condensing 3-methyl pyrazolone with 4-formyl coumarin. The synthesized molecules were evaluated for in vitro anti-inflammatory and anticancer activities.…”

Section: Recently Reported Cox Inhibitorsmentioning

confidence: 99%

Design and Development of COX-II Inhibitors: Current Scenario and Future Perspective

et al. 2023

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Innate inflammation beyond a threshold is a significant problem involved in cardiovascular diseases, cancer, and many other chronic conditions. Cyclooxygenase (COX) enzymes are key inflammatory markers as they catalyze prostaglandins production and are crucial for inflammation processes. While COX-I is constitutively expressed and is generally involved in "housekeeping" roles, the expression of the COX-II isoform is induced by the stimulation of different inflammatory cytokines and also promotes the further generation of pro-inflammatory cytokines and chemokines, which affect the prognosis of various diseases. Hence, COX-II is considered an important therapeutic target for drug development against inflammation-related illnesses. Several selective COX-II inhibitors with safe gastric safety profiles features that do not cause gastrointestinal complications associated with classic antiinflammatory drugs have been developed. Nevertheless, there is mounting evidence of cardiovascular side effects from COX-II inhibitors that resulted in the withdrawal of market-approved anti-COX-II drugs. This necessitates the development of COX-II inhibitors that not only exhibit inhibit potency but also are free of side effects. Probing the scaffold diversity of known inhibitors is vital to achieving this goal. A systematic review and discussion on the scaffold diversity of COX inhibitors are still limited. To address this gap, herein we present an overview of chemical structures and inhibitory activity of different scaffolds of known COX-II inhibitors. The insights from this article could be helpful in seeding the development of next-generation COX-II inhibitors.

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Section: Recently Reported Cox Inhibitorsmentioning

confidence: 99%

Design and Development of COX-II Inhibitors: Current Scenario and Future Perspective

et al. 2023

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“…A series of novel synthesized coumarin-pyrazolones with excellent yield were screened for their anticancer activities at NCI60. The compound with methoxy on coumarin nucleus (17) showed marked action at 10 −5 M concentration with respect to different oncogenic cell lines (Kulkarni et al, 2018).…”

Section: Coumarin-pyrazolone Hybrids As An Anticancer Agentmentioning

confidence: 99%

Pyrazolones as a potential anticancer scaffold: Recent trends and future perspectives

Suman¹,

Singh²,

Sandeep³

2021

J Appl Pharm Sci

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Cancers are already placing an enormous load on the worldwide healthcare practice; so, anti-neoplastic compounds nowadays are most essential in cancer remedy. Nevertheless, the expanding resistance in drug profiles' appearance in recently available anticancer drugs has so far risen to a distressing level over past decades. Pyrazolone holds wideranging chemotherapeutic characteristics, including anticancer activity, and they inhabit a significant place in the novel drug development process. As per the literature, various hybridized pyrazolone moieties with different pharmacophores and pyrazolone metal complexes have anticancer activities with good potency. In recent years, pyrazolone hybrids and metal complexes were generated to study their anticancer properties. Out of these, some derivatives displayed promising strengths against the case of resistant and susceptible cell lines of cancer. This current review encloses the latest advances of pyrazolone hybrids including thiophene, aminomethylidenes , naphthoquinones, combretastatins, 2-substituted-4-(2-fluorophenoxy) pyridine, hydroxybenzo[a]phenazine, coumarin, dihydrobenzoxepine, cyclic peptide, cambinol derivatives of pyrazolone, and different metal complexes as a potential anticancer agent.

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“…[3,4] Pyrazolone is one of the important class of heterocyclic compounds and the primary structural component of numerous molecules with biological and pharmacological effects. A wide range of biological effects, including anti-inflammatory, [5] antibacterial, [6] antidepressant, antitubercular [7] and anticancer [8] are displayed by them. The insertion of heterocyclic rings into prospective candidates is a crucial technique utilized to create more effective and selective pharmaceutical prospects.…”

Section: Introductionmentioning

confidence: 99%

“…synthesized series of novel coumarin‐pyrazolones with excellent yield for their anticancer activities with different substituent like methoxy, methyl group on coumarin nucleus. Compounds 3 showed marked anticancer activity against non‐small lung cancer cell line (NCI−H23) and breast cancer (T‐47D) and compound 4 is moderately active against both (NCI−H23) and (T‐47D) [16] . Therefore, coumarin moiety hybridized with additional anticancer pharmacophores may result in novel anticancer candidates with low toxicity, high specificity, and great efficacy against both drug‐susceptible and drug‐resistant cancers.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of pyrazolone derivatives of coumarin as anticancer agents

Patil,

Soman,

Umar

et al. 2024

ChemistrySelect

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Pursuing on our efforts towards searching for efficient anticancer agents herein we have designed and synthesized pyrazolone derivatives of 7‐amino 4‐methyl coumarin and 6‐amino coumarin. Anticancer activity of all the compounds were performed against lungs cancer cell line (A549) and breast cancer cell line (MCF‐7) using MTT assay. Out of all the compounds, compounds 17 c and 19 b exhibited remarkable activity with IC50 value of 1.22 μM and 1.66 μM against lungs cancer cell line (A549) breast cancer cell line (MCF‐7) respectively. Consequently, both compounds 17 c and compound 19 b were selected to study their cytotoxicity mechanism using different assays which includes EtBr/AO assay in respective cell, quantification of ROS using DCFH‐DA dye. To explore the behavioral and selective properties of the synthesized molecules, experimental analysis was complemented with computational methods. The electronic and structural parameters for both compound 17 c and 19 b were calculated using density functional theory (DFT) calculations and correlated with the observed biological activity. Molecular docking was conducted to explore the interaction of compounds 17 c and 19 b with pivotal apoptotic genes, namely p53 and caspase 3. Compound 17 c exhibited docking scores of −8.6 and −8.4 kcal/mol for p53 and caspase 3, while compound 19 b showed scores of −9.3 kcal/mol for both genes, significantly surpassing fluorouracil. Hence, compound 17 c and 19 b can be pursued for further studies, including molecular and In Vivo investigations.

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Green synthesis of coumarin-pyrazolone hybrids: In vitro anticancer and anti-inflammatory activities and their computational study on COX-2 enzyme

Cited by 10 publications

References 23 publications

Design and Development of COX-II Inhibitors: Current Scenario and Future Perspective

Design and Development of COX-II Inhibitors: Current Scenario and Future Perspective

Pyrazolones as a potential anticancer scaffold: Recent trends and future perspectives

Synthesis of pyrazolone derivatives of coumarin as anticancer agents

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