Synthesis, in-vitro screening, and docking analysis of novel pyrrolidine and piperidine-substituted ethoxy chalcone as anticancer agents

Mokale, Santosh N.; Dube, Pritam N.; Bhavale, Swati A.; Sayed, Ibrahim El Tantawy El; Begum, Afreen; Nevase, Manjusha C.; Shelke, Vishakha R.; Mujaheed, Abdul

doi:10.1007/s00044-014-1266-8

Cited by 25 publications

(13 citation statements)

References 31 publications

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“…The proposed derivatives were synthesized in three steps and their structures were verified by IR, 1 H‐NMR, 13 C‐NMR, and LC‐MS spectroscopy. The first step in the synthetic route consisted of the Claisen–Schmidt condensation of 4′‐hydroxyl acetophenone with substituted benzaldehydes and 4′‐hydroxyl benzaldehydes with substituted acetophenone in basic conditions (10% aqueous KOH) to give α , β ‐unsaturated ketones (chalcones, Scheme ) . The second step consisted of the condensation of hydroxyl group by amino side chain.…”

Section: Resultsmentioning

confidence: 99%

“…An equimolar mixture of 4‐hydroxy acetophenone, substituted benzaldehydes, and KOH (2 mmol) was stirred in PEG‐400 (15 mL) at 40 °C for 2–3 h. After the completion of the reaction (monitored by TLC), the crude mixture was worked up in ice‐cold water (100 mL). The resultant product was separated out and recrystallized from absolute ethanol .…”

Section: Methodsmentioning

confidence: 99%

“…The organic layer was washed with water, brine and dried over anhydrous Na 2 SO 4 . The precipitate was recrystallized from absolute ethanol .…”

Section: Methodsmentioning

confidence: 99%

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Synthesis, in Vitro, and in Vivo Biological Evaluation and Molecular Docking Analysis of Novel 3‐(3‐oxo‐substitutedphenyl‐3‐)4‐(2‐(piperidinyl)ethoxy)phenyl)propyl)‐2H‐chromen‐2‐one Derivatives as Anti‐breast Cancer Agents

2015

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The analogs of coumarin-chalcones have been reported to exhibit antineoplastic, anti-allergic, antihepatoprotective, and estrogenic activity. Herein, we have reported 3-(3-oxo-substitutedphenyl-3-)4-(2-(piperidinyl)ethoxy)phenyl)propyl)-2H-chromen-2-one derivatives as a new class of compounds that exhibit selectivity for ER-α binding along with antiproliferative and cytotoxic activity on human breast cancer cell line. The active compounds which show prominent activity against estrogen receptor-alpha-positive (ER+) human breast cancer cell lines MCF-7 and Zr-75-1 are subjected to in vivo screening. The Glide XP docking was performed for designed scaffold to optimize its structural requirement for ER-α inhibition.

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Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

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Synthesis, in Vitro, and in Vivo Biological Evaluation and Molecular Docking Analysis of Novel 3‐(3‐oxo‐substitutedphenyl‐3‐)4‐(2‐(piperidinyl)ethoxy)phenyl)propyl)‐2H‐chromen‐2‐one Derivatives as Anti‐breast Cancer Agents

2015

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“…The organic layer was washed with water and brine, and it was dried over anhydrous Na2SO4. The precipitate was recrystallized from absolute ethanol [7,8].…”

Section: Synthesis Of Target Compounds (5a-f)mentioning

confidence: 99%

“…Results were given in terms of GI50, TGI, and LC50 values. The compounds were tested for their cytotoxic assay using MCF-7and ZR-75-1 breast cancer cell lines [8,9].…”

Section: In-vitro Antitumor Activitymentioning

confidence: 99%

Design and Synthesis of Novel Chalcone-Phenylpyranone Derivatives as Estrogen Receptor Modulators

Dube¹,

Thombare²,

Chatpalliwar³

2018

22nd International Electronic Conference on Synthetic Organic Chemistry

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Selective estrogen receptor modulators (SERMs) are a class of drugs that act on the estrogen receptor (ER). SERMs are used for treatment and reduction of risk of breast cancer. Herewith we had designed, synthesized, and evaluated chalcone-phenylpyran-2-one derivatives bearing a N,N-dimethyl ethylamine side chain for their anti-breast cancer activity on MCF-7 and Zr-75-1 cell lines in-vitro. The pharmacological data indicated that most of tested compounds showed moderate to significant cytotoxicity and high selectivity toward the estrogen receptor. The Structure activity relationaship analyses indicated that compounds 5f with 2,6-dichloro substitution was more effective. Docking study was performed to predict binding orientation towards the estrogen receptor-α.

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Chalcone hybrids as potential anticancer agents: Current development, mechanism of action, and structure‐activity relationship

Gao

Huang

Xiao

2020

Medicinal Research Reviews

101

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The continuous emergency of drug‐resistant cancers and the low specificity of anticancer agents have been the major challenges in the control and treatment of cancer, making an urgent need to develop novel anticancer agents with high efficacy. Chalcones, precursors of flavonoids and isoflavonoids, exhibit structural heterogeneity and can act on various drug targets. Chalcones which demonstrated potential in vitro and in vivo activity against both drug‐susceptible and drug‐resistant cancers, are useful templates for the development of novel anticancer agents. Hybridization of chalcone moiety with other anticancer pharmacophores could provide the hybrids which have the potential to overcome drug resistance and improve the specificity, so it represents a promising strategy to develop novel anticancer agents. This review emphasizes the development, the mechanisms of action as well as structure‐activity relationships of chalcone hybrids with potential therapeutic application for many cancers in recent 10 years.

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Synthesis, in-vitro screening, and docking analysis of novel pyrrolidine and piperidine-substituted ethoxy chalcone as anticancer agents

Cited by 25 publications

References 31 publications

Synthesis, in Vitro, and in Vivo Biological Evaluation and Molecular Docking Analysis of Novel 3‐(3‐oxo‐substitutedphenyl‐3‐)4‐(2‐(piperidinyl)ethoxy)phenyl)propyl)‐2H‐chromen‐2‐one Derivatives as Anti‐breast Cancer Agents

Synthesis, in Vitro, and in Vivo Biological Evaluation and Molecular Docking Analysis of Novel 3‐(3‐oxo‐substitutedphenyl‐3‐)4‐(2‐(piperidinyl)ethoxy)phenyl)propyl)‐2H‐chromen‐2‐one Derivatives as Anti‐breast Cancer Agents

Design and Synthesis of Novel Chalcone-Phenylpyranone Derivatives as Estrogen Receptor Modulators

Chalcone hybrids as potential anticancer agents: Current development, mechanism of action, and structure‐activity relationship

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