Synthesis and biological activity of 2,4-di-p-phenolyl-6-2-furanyl-pyridine as a potent topoisomerase II poison

Karki, Radha; Park, Chanmi; Jun, Kyu‐Yeon; Kadayat, Tara Man; Lee, Eung-Seok; Kwon, Young Joo

doi:10.1016/j.ejmech.2014.11.045

Cited by 26 publications

(5 citation statements)

References 46 publications

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“…The topoisomerase (Topo) inhibitors are molecules which (a) disrupt enzyme activity by forming ternary complex (DNA-Topo-compound)-these compounds were named as topoisomerase poisons-or (b) molecules which inhibit the catalytic function of enzymes-named catalytic inhibitors-and affect both to result in cell death (apoptosis) [73,[81][82][83][84]. We performed Topo-mediated DNA relaxation or decatenation assays to test whether the new class of acridine derivatives 3a-3d exert their antiproliferative function by targeting Topo.…”

Section: Inhibition Of Topoisomerase I and Iimentioning

confidence: 99%

Acridine Based N-Acylhydrazone Derivatives as Potential Anticancer Agents: Synthesis, Characterization and ctDNA/HSA Spectroscopic Binding Properties

et al. 2022

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A series of novel acridine N-acylhydrazone derivatives have been synthesized as potential topoisomerase I/II inhibitors, and their binding (calf thymus DNA—ctDNA and human serum albumin—HSA) and biological activities as potential anticancer agents on proliferation of A549 and CCD-18Co have been evaluated. The acridine-DNA complex 3b (-F) displayed the highest Kb value (Kb = 3.18 × 103 M−1). The HSA-derivatives interactions were studied by fluorescence quenching spectra. This method was used for the calculation of characteristic binding parameters. In the presence of warfarin, the binding constant values were found to decrease (KSV = 2.26 M−1, Kb = 2.54 M−1), suggesting that derivative 3a could bind to HSA at Sudlow site I. The effect of tested derivatives on metabolic activity of A549 cells evaluated by the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide or MTT assay decreased as follows 3b (-F) > 3a(-H) > 3c(-Cl) > 3d(-Br). The derivatives 3c and 3d in vitro act as potential dual inhibitors of hTopo I and II with a partial effect on the metabolic activity of cancer cells A594. The acridine-benzohydrazides 3a and 3c reduced the clonogenic ability of A549 cells by 72% or 74%, respectively. The general results of the study suggest that the novel compounds show potential for future development as anticancer agents.

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Section: Inhibition Of Topoisomerase I and Iimentioning

confidence: 99%

Acridine Based N-Acylhydrazone Derivatives as Potential Anticancer Agents: Synthesis, Characterization and ctDNA/HSA Spectroscopic Binding Properties

et al. 2022

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“…Traditional basic catalysts were replaced by organic base [147] and solid superbase [148] which realized higher selectivity and yield. A variety of acid catalysts including hydrochloric acid [149], para-toluenesulfonic acid [150] and Lewis acids [151,152] were also applied, especially suitable for the aromatic aldehydes with phenolic hydroxyls. Chalcones can also be produced through cross-coupling reaction of benzoic or cinnamate derivatives with organoboron or organometallic compounds mainly including arylboronic acids, aryllithium and arylstannanes catalyzed by transition metal catalysts [153][154][155] (Scheme 16b).…”

Section: Total-synthesis Strategies Of Chalcone Derivativesmentioning

confidence: 99%

Structural derivatization strategies of natural phenols by semi-synthesis and total-synthesis

Ding

Jiang

Zhang

et al. 2022

Nat. Prod. Bioprospect.

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Structural derivatization of natural products has been a continuing and irreplaceable source of novel drug leads. Natural phenols are a broad category of natural products with wide pharmacological activity and have offered plenty of clinical drugs. However, the structural complexity and wide variety of natural phenols leads to the difficulty of structural derivatization. Skeleton analysis indicated most types of natural phenols can be structured by the combination and extension of three common fragments containing phenol, phenylpropanoid and benzoyl. Based on these fragments, the derivatization strategies of natural phenols were unified and comprehensively analyzed in this review. In addition to classical methods, advanced strategies with high selectivity, efficiency and practicality were emphasized. Total synthesis strategies of typical fragments such as stilbenes, chalcones and flavonoids were also covered and analyzed as the supplementary for supporting the diversity-oriented derivatization of natural phenols.

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“…TopoIIα inhibitors can be broadly divided into two classes. The first one, termed TopoIIα poisons, can stabilize the TopoIIα-DNA cleavage complex, leading to DNA strand breaks [3,5].…”

Section: Introductionmentioning

confidence: 99%

Design and synthesis of 2-phenylnaphthalenoids and 2-phenylbenzofuranoids as DNA topoisomerase inhibitors and antitumor agents

Hao

Chen

Zhu

et al. 2015

European Journal of Medicinal Chemistry

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Synthesis and biological activity of 2,4-di-p-phenolyl-6-2-furanyl-pyridine as a potent topoisomerase II poison

Cited by 26 publications

References 46 publications

Acridine Based N-Acylhydrazone Derivatives as Potential Anticancer Agents: Synthesis, Characterization and ctDNA/HSA Spectroscopic Binding Properties

Acridine Based N-Acylhydrazone Derivatives as Potential Anticancer Agents: Synthesis, Characterization and ctDNA/HSA Spectroscopic Binding Properties

Structural derivatization strategies of natural phenols by semi-synthesis and total-synthesis

Design and synthesis of 2-phenylnaphthalenoids and 2-phenylbenzofuranoids as DNA topoisomerase inhibitors and antitumor agents

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