First synthesis of novel 2,4-bis((<i>E</i>)-styryl)quinoline-3-carboxylate derivatives and their antitumor activity

Gao, Wentao; Li, Zhiyuan; Xu, Qi-Qi; Li, Yang

doi:10.1039/c8ra08023b

Cited by 11 publications

(6 citation statements)

References 45 publications

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“…Such interlinking helps extend the π-conjugation of 8-HQs, enhancing the molecule’s overall electron mobility, thermal stability, and lipophilicity. As a result, the 2S-8HQs exhibit improved photophysical, conductive, and biological properties compared to simple 8-HQs. − By introducing suitable functional substituents on the styryl and quinoline rings, the properties of 2S-8HQs can be improved. 2S-8HQs exhibit important pharmacological activities, including anticancer, anti-HIV-1, antimicrobial, antimalarial, and anti-Alzheimer activities. − In addition, the 2S-8HQs are also explored as organic semiconductors, − thermo and electrochromic materials, and organic light-emitting diode (OLED) materials. ,,− Still, compared to many other derivatives of 8-HQs, 2S-8HQs are a relatively less explored class of compounds, and there is an ongoing interest in developing structurally diversified 2S-8HQs for varied applications.…”

Section: Introductionmentioning

confidence: 99%

Substituent-Controlled Structural, Supramolecular, and Cytotoxic Properties of a Series of 2-Styryl-8-nitro and 2-Styryl-8-hydroxy Quinolines

et al. 2022

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Styryl quinolines are biologically active compounds with properties largely depending on the substituents on the styryl and quinoline rings. The supramolecular aspects of this class of compounds are rarely explored. In this study, two new series of styryl quinoline derivatives, bearing −OH and −NO 2 groups at the eighthposition of the quinoline ring and −SCH 3 , −OCH 3 , and −Br groups on the styryl ring, have been developed, and their structural, supramolecular, and cytotoxic properties have been analyzed. Crystallographic analyses revealed the exciting substituent-dependent structural and supramolecular features of these compounds. In general, the 8 −OH substituted derivatives ( SA series) exhibited a non-planar molecular geometry having larger dihedral angles (5.75–59.3°) between the planes of the aromatic rings. At the same time, the 8 −NO 2 substituted derivatives ( SB series) exhibited a more or less planar molecular geometry, as revealed by the smaller dihedral angles (1.32–3.45°) between the aromatic rings. Multiple O–H···O, C–H···O, O–H···N, and π–π stacking interactions among the molecules lead to fascinating supramolecular architectures such as hydrogen-bonded triple helices, zig-zag 1D chains, π–π stacked infinite chains, and so forth in their crystal lattice. Hirshfeld surface analyses confirmed the existence of strong π–π stacking and other weak bonding interactions in these compounds. The preliminary cytotoxic properties of SA and SB series compounds were evaluated against the human cervical cancer cell lines (HeLa cells), which further highlighted the roles of functional substituents on the aromatic rings. The SA series compounds with the −OH substituent on the quinoline ring exhibited better cytotoxicity than the SB series compounds with a −NO 2 substituent. Similarly, the electron-withdrawing group −Br on the styryl ring enhanced the cytotoxicity in both series. The IC 50 values were 2.52–4.69 and 2.897–10.37 μM, respectively, for the SA and SB series compounds. Compound S3A having −OH and −Br groups on the quinoline and styryl ring, respectively, exhibited the best IC 50 value of 2.52 μM among all the compounds tested. These findings confirm the relevance of the hydroxyl group in the eighth position of quinoline. In short, the present study attempts to provide a systematic analysis of the effects of aromatic ring substituents on the structural, supramolecular, and cytotoxic properties of styryl quinolines for the first time.

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Section: Introductionmentioning

confidence: 99%

Substituent-Controlled Structural, Supramolecular, and Cytotoxic Properties of a Series of 2-Styryl-8-nitro and 2-Styryl-8-hydroxy Quinolines

et al. 2022

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“…By refluxing mixture of 5-aminomethyl-8-hydroxyquinoline (218) with pentyl bromide and triethylamine in tetrahydrofuran (THF) for 6 h. [59] All these derivatives were evaluated for antitumor activity on human cancer cell lines(A549, HT29 and T24) and it was observed that compound 236 h, k, t (R = 3,4-diMeOC 6 H 5 , 3,4,5-TriMeOC 6 H 2 , Ferrocenyl) showed excellent activity with IC 50 values of 1.53,1.38 and 2.36 μM against A549 and 1.50, 0.77 and 0.97 μM against HT29 respectively. [63] were condensed in presence of SnCl 2 catalyst, AcOH and ethyl alcohol with refluxing. This process takes place via formation of benzylidine intermediate followed by elimination and cylclisation to synthesise compound (240).…”

Section: Chemistryselectmentioning

confidence: 99%

“…All these derivatives were evaluated for antitumor activity on human cancer cell lines(A549, HT29 and T24) and it was observed that compound 236 h , k , t (R=3,4‐diMeOC 6 H 5 , 3,4,5‐TriMeOC 6 H 2 , Ferrocenyl) showed excellent activity with IC 50 values of 1.53,1.38 and 2.36 μM against A549 and 1.50, 0.77 and 0.97 μM against HT29 respectively [63] . (Scheme 48 )…”

Section: Introductionmentioning

confidence: 99%

Chemistry of Quinoline Based Heterocycle Scaffolds: A Comprehensive Review

et al. 2022

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Quinoline is a significant scaffold among heterocyclic compounds and can be used as a key building block for the development of novel medications. Quinoline and its derivatives are recognised as biologically active substances with a number of pharmacological properties. Nowadays, quinolinebased heterocycle scaffolds have achieved a prominent position in medicinal chemistry due to their significant pharmaco-logical and biological properties. The discovery and creation of cutting-edge medications to treat a variety of diseases is an example of the usefulness of these compounds. The current study outlines the range of methods available to create different quinolone-based heterocycle scaffolds and their advantageous therapeutic applications using the literature that has been published up to 2022.

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“…Styrylquinolines constitute an important group of quinoline derivatives with high medicinal value due to their broad spectrum of bioactivities (Musiol, 2020), finding therapeutic applications as potential anticancer (Gao et al, 2018;Mrozek-Wilczkiewicz et al, 2019), antifungal (Cieslik et al, 2012), antileishmanial (Luczywo et al, 2021) and antiretroviral (Mouscadet & Desmae ¨le, 2010) agents.…”

Section: Introductionmentioning

confidence: 99%

A three-step pathway from (2-aminophenyl)chalcones to novel styrylquinoline–chalcone hybrids: synthesis and spectroscopic and structural characterization of three examples

et al. 2023

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Three new styrylquinoline–chalcone hybrids have been synthesized using a three-step pathway starting with Friedländer cyclocondensation between (2-aminophenyl)chalcones and acetone to give 2-methyl-4-styrylquinolines, followed by selective oxidation to the 2-formyl analogues, and finally Claisen–Schmidt condensation between the formyl intermediates and 1-acetylnaphthalene. All intermediates and the final products have been fully characterized by IR and 1H/13C NMR spectroscopy, and by high-resolution mass spectrometry, and the three products have been characterized by single-crystal X-ray diffraction. The molecular conformations of (E)-3-{4-[(E)-2-phenylethenyl]quinolin-2-yl}-1-(naphthalen-1-yl)prop-2-en-1-one, C30H21NO, (IVa), and (E)-3-{4-[(E)-2-(4-fluorophenyl)ethenyl]quinolin-2-yl}-1-(naphthalen-1-yl)prop-2-en-1-one, C30H20FNO, (IVb), are very similar. In each compound, the molecules are linked into a three-dimensional array by hydrogen bonds, of the C—H...O and C—H...N types in (IVa), and of the C—H...O and C—H...π types in (IVb), and by two independent π–π stacking interactions. By contrast, the conformation of the chalcone unit in (E)-3-{4-[(E)-2-(2-chlorophenyl)ethenyl]quinolin-2-yl}-1-(naphthalen-1-yl)prop-2-en-1-one, C30H20ClNO, (IVc), differs from those in (IVa) and (IVb). There are only weak hydrogen bonds in the structure of (IVc), but a single rather weak π–π stacking interaction links the molecules into chains. Comparisons are made with some related structures.

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First synthesis of novel 2,4-bis((E)-styryl)quinoline-3-carboxylate derivatives and their antitumor activity

Abstract: One-pot successive Arbuzov/HWE synthesis and preliminary antitumor activity evaluation of 2,4-di((E)-styryl)quinoline-3-carboxylates was described in this study.

Cited by 11 publications

References 45 publications

Substituent-Controlled Structural, Supramolecular, and Cytotoxic Properties of a Series of 2-Styryl-8-nitro and 2-Styryl-8-hydroxy Quinolines

Substituent-Controlled Structural, Supramolecular, and Cytotoxic Properties of a Series of 2-Styryl-8-nitro and 2-Styryl-8-hydroxy Quinolines

Chemistry of Quinoline Based Heterocycle Scaffolds: A Comprehensive Review

A three-step pathway from (2-aminophenyl)chalcones to novel styrylquinoline–chalcone hybrids: synthesis and spectroscopic and structural characterization of three examples

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