Synthesis of newer piperidinyl chalcones and their anticancer activity in human cancer cell lines

Jayashree, B. S.; Patel, Harshkumar H.; Mathew, Neethu Susan; Nayak, Yogendra

doi:10.1007/s11164-015-2238-4

Cited by 10 publications

(5 citation statements)

References 27 publications

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“… Heterocyclic chalcones with anti-breast-cancer activity [ 23 , 184 , 185 , 186 , 187 , 188 , 189 , 190 , 191 , 192 , 193 , 194 , 195 , 196 , 197 , 198 , 199 , 200 , 201 , 202 , 203 , 204 , 205 , 206 , 207 , 208 ]. …”

Section: Figures Schemes and Tablesunclassified

Chalcone: A Promising Bioactive Scaffold in Medicinal Chemistry

et al. 2022

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Chalcones are a class of privileged scaffolds with high medicinal significance due to the presence of an α,β-unsaturated ketone functionality. Numerous functional modifications of chalcones have been reported, along with their pharmacological behavior. The present review aims to summarize the structures from natural sources, synthesis methods, biological characteristics against infectious and non-infectious diseases, and uses of chalcones over the past decade, and their structure–activity relationship studies are detailed in depth. This critical review provides guidelines for the future design and synthesis of various chalcones. In addition, this could be highly supportive for medicinal chemists to develop more promising candidates for various infectious and non-infectious diseases.

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Section: Figures Schemes and Tablesunclassified

Chalcone: A Promising Bioactive Scaffold in Medicinal Chemistry

et al. 2022

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“…Lipophilicity 19 is one of the important experimental molecular descriptors, which helps in the determination of biological activity for drug candidates. In the present study, majority of the test compounds showed promising cytotoxicity, that possessed a log D values at the pH 7.4 values in the range between 2.4-4.2 as showed in Table 3.…”

Section: Determination Of Lipophilicitymentioning

confidence: 99%

“…(APCI +ve mode): m/z 460 19,. [M+2] + 1 H NMR: δ 2.28-2.40 (5H, 2.28 (s), 2.34 (ddd, J = 15.0, 3.8, 2.0 Hz)), 2.72 (2H, ddd, J = 11.4, 3.8, 2.0 Hz), 3.08 (2H, dd, J = 13.9, 4.3 Hz), 3.85-3.87 (6H, 3.86 (s), 3.86 (s)), 5.98 (1H, dd, J = 4.3, 2.2 Hz), 6.12 (1H, s), 6.73 (1H, d, J = 15.7 Hz), 7.29-7.39 (2H, 7.35 (ddd, J = 8.1, 1.9, 1.…”

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confidence: 99%

Design, Synthesis and Biological Evaluation of Novel Piperidinyl Chalcones

Pai¹,

Jayashree²

2019

IJPER

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Aim/Background: Chalcones are one of the important class of compounds possessing a wide range of biological properties [Dinmock 1999, Go 2005]. One of the extensive area in research on chalcones is expressed in terms of their ability to act on various cancer cell lines by a variety of molecular mechanisms. Chalcones possessing methoxy groups, a trimethoxy substituted chalcone (PGHSD 234) is the most potent chalcone with cytotoxicity comparable to the standard drugs. Materials and Methods: The antioxidant potential in terms of their free radical scavenging ability and antiproliferative activities were evaluated. Log P value and cyclic Voltammetric studies were carried out to assess their hydrophobicity and to determine their anti-oxidant potential. MTT (methyl tetrazolium) assay was performed on two cell lines including Vero and MCF-7 cell lines. Molecular docking studies were performed to assess the binding pattern of synthesized chalcones into the ATP binding site of CDK2/Cyclin A protein target. Results: The MTT assay results showed the effect of various substituents on the chalcone template that could influence their cytotoxic effect. The hydrophobicity of the synthesized compounds were reported as distribution coefficient (Log D) and all the compounds showed Log D values in the range of 1.45-4.0. The cyclic voltammetric studies revealed their irreversible oxidation potential and were found in the range of-0.400 to-0.654. Conclusion: The present study provides insight for the better understanding of mechanistic studies of N-methyl piperidinyl chalcones against anticancer targets such as CDK and aromatase identified in breast cancer.

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“…On top of this, many researchers are exhaustively devoted to synthesizing a chalcone derivative incorporating a heterocyclic scaffold. Chalcones incorporating heterocyclic scaffolds have been reported with various biological and pharmacological activities, such as antioxidant activity, 12 antibacterial activity, 12 antifungal activity, 13 antileishmanial activity, 14 anti-inflamatory activity, 15 anticancer activity, 16 antitubercular activity, 17 antiproliferative agents, 17 antimalarial activity, 18 antiplatelet activity, 19 carbonic anhydrase inhibitors, 20 an inhibitor of microsomalenzyme glutathione-S-transferases, 21 and CYP1 enzyme inhibitors. 22 Chalcones with an N-heterocyclic moiety such as pyrrole, imidazole, thiazole, pyrazole, oxazole, isooxazole, pyridine, pyrazoline, indole, benzothiazole, benzimidazole, and quinoline scaffolds play a significant role in the area of medicine.…”

Section: ■ Introductionmentioning

confidence: 99%

Synthesis and Pharmacological Activities of Chalcone and Its Derivatives Bearing N-Heterocyclic Scaffolds: A Review

2023

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The incorporation of heterocyclic moieties into the standard chemical structure with a biologically active scaffold has become of crucial practice for the construction of pharmacologically potent candidates in the drug arena. Currently, numerous kinds of chalcones and their derivatives have been synthesized using the incorporation of heterocyclic scaffolds, especially chalcones bearing heterocyclic moieties that display improved efficiency and potential for drug production in pharmaceutical sectors. The current Review focuses on recent advances in the synthetic approaches and pharmacological activities such as antibacterial, antifungal, antitubercular, antioxidant, antimalarial, anticancer, antiinflammatory, antigiardial, and antifilarial activities of chalcone derivatives incorporating N-heterocyclic moieties at either the A-ring or B-ring.

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Synthesis of newer piperidinyl chalcones and their anticancer activity in human cancer cell lines

Cited by 10 publications

References 27 publications

Chalcone: A Promising Bioactive Scaffold in Medicinal Chemistry

Chalcone: A Promising Bioactive Scaffold in Medicinal Chemistry

Design, Synthesis and Biological Evaluation of Novel Piperidinyl Chalcones

Synthesis and Pharmacological Activities of Chalcone and Its Derivatives Bearing N-Heterocyclic Scaffolds: A Review

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