Synthesis and anticancer potential of novel xanthone derivatives with 3,6-substituted chains

Liu, Chaomei; Zhang, Mei; Zhang, Zhenhuan; Zhang, Steven B.; Yang, Shanmin; Zhang, Amy; Yin, Liangjie; Swarts, Steven G; Vidyasagar, Sadasivan; Zhang, Lurong; Okunieff, Paul

doi:10.1016/j.bmc.2016.07.020

Cited by 26 publications

(15 citation statements)

References 27 publications

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“…Morpholino ethyl substitution at 4‐position as in compound 16 showed no significant activity. When the anticancer activities of the morpholine compound 16 and the piperidine compound 17 were compared, the decrease in the activity of the morpholine ring could be due to the oxygen atom making hydrogen bonds with the biological macromolecules . Compared with compound 1 , compound 15 with the cyclohexyl group was more potent with the IC 50 value of 37.6 μM.…”

Section: Resultsmentioning

confidence: 99%

Design and Synthesis of Novel Thioureas Derived from 4‐(4‐Fluorophenoxy)aniline as Anticancer Agents

Yıldız

Oruç‐Emre

Tasdemir

et al. 2017

J Chinese Chemical Soc

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A new series of thiourea derivatives were obtained by the reaction of 4‐(4‐fluorophenoxy) aniline with different isothiocyanates. Their chemical structures were confirmed by ultraviolet (UV), infrared (IR), nuclear magnetic resonance (NMR), and mass spectral data and elemental analysis. All the synthesized thiourea derivatives were evaluated for their in vitro cancer activity against the human breast cancer cell lines MCF‐7 (human breast adenocarcinoma) and SKBr‐3 (human epithelial breast adenocarcinoma). Most of the derivatives exhibited significant anticancer activity. Especially, compound 3 showed the most potent activity (IC50 20.1 μM) against SKBr‐3 when compared with the drugs 5‐fluorouracil and cisplatin, and, most importantly, it did not affect normal breast epithelial cells (4010).

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Section: Resultsmentioning

confidence: 99%

Design and Synthesis of Novel Thioureas Derived from 4‐(4‐Fluorophenoxy)aniline as Anticancer Agents

Yıldız

Oruç‐Emre

Tasdemir

et al. 2017

J Chinese Chemical Soc

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“…To date, more than 50% of the marketed drugs were developed from natural products, especially secondary metabolites and their derivatives 23,24 . Xanthones are one of these important secondary metabolites that possessed a broad spectrum of biological activities such as anti-cancer 25 , antioxidant 26 , antibacterial 27 , antifungal 28 , antimalarial 29 , antidiabetic 30,31 , anti-cholinergic 15,32 and anti-inflammatory activities [33][34][35][36] .…”

Section: Introductionmentioning

confidence: 99%

New 3-O-substituted xanthone derivatives as promising acetylcholinesterase inhibitors

Loh

Kwong

Lam

et al. 2021

Journal of Enzyme Inhibition and Medicinal Chemistry

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A new series of 3-O-substituted xanthone derivatives were synthesised and evaluated for their anti-cholinergic activities against acetylcholinesterase (AChE) and butyrylcholinesterase (BChE). The results indicated that the xanthone derivatives possessed good AChE inhibitory activity with eleven of them (5, 8, 11, 17, 19, 21-23, 26-28) exhibited significant effects with the IC 50 values ranged 0.88 to 1.28 mM. The AChE enzyme kinetic study of 3-(4-phenylbutoxy)-9H-xanthen-9-one (23) and ethyl 2-((9-oxo-9H-xanthen-3-yl)oxy)acetate (28) showed a mixed inhibition mechanism. Molecular docking study showed that 23 binds to the active site of AChE and interacts via extensive p-p stacking with the indole and phenol side chains of Trp86 and Tyr337, besides the hydrogen bonding with the hydration site and p-p interaction with the phenol side chain of Y72. This study revealed that 3-O-alkoxyl substituted xanthone derivatives are potential lead structures, especially 23 and 28 which can be further developed into potent AChE inhibitors.

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“…The anticancer and immunomodulatory effects of natural and synthetic xanthones have been extensively reported in the literature [10,13,24,48,49,50,51,52], including those of 1,2-DHX [15,20]. Despite these insights, as far as we know, no studies have yet been undertaken to clarify the effects of 1,2-DHX on macrophages, which may have an impact on melanoma cell growth.…”

Section: Discussionmentioning

confidence: 99%

1,2-Dihydroxyxanthone: Effect on A375-C5 Melanoma Cell Growth Associated with Interference with THP-1 Human Macrophage Activity

et al. 2019

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Xanthones have been suggested as prospective candidates for cancer treatment. 1,2- dihydroxyxanthone (1,2-DHX) is known to interfere with the growth of several cancer cell lines. We investigated the effects of 1,2-DHX on the growth of the A375-C5 melanoma cell line and THP-1 human macrophage activity. 1,2-DHX showed a moderate growth inhibition of A375-C5 melanoma cells (concentration that causes a 50% inhibition of cell growth (GI50) = 55.0 ± 2.3 µM), but strongly interfered with THP-1 human macrophage activity. Supernatants from lipopolysaccharide (LPS)-stimulated THP-1 macrophage cultures exposed to 1,2-DHX significantly increased growth inhibition of A375-C5 cells, when compared to supernatants from untreated LPS-stimulated macrophages or to direct treatment with 1,2-DHX only. 1,2-DHX decreased THP-1 secretion of interleukin-1β (IL-1β) and interleukin-10 (IL-10), but stimulated tumor necrosis factor-α (TNF-α) and transforming growth factor-β1 (TGF-β1) production. This xanthone also inhibited nitric oxide (NO) production by RAW 264.7 murine macrophages, possibly through inhibition of inducible NO synthase production. In conclusion, these findings suggest a potential impact of 1,2-DHX in melanoma treatment, not only due to a direct effect on cancer cells but also by modulation of macrophage activity.

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Synthesis and anticancer potential of novel xanthone derivatives with 3,6-substituted chains

Cited by 26 publications

References 27 publications

Design and Synthesis of Novel Thioureas Derived from 4‐(4‐Fluorophenoxy)aniline as Anticancer Agents

Design and Synthesis of Novel Thioureas Derived from 4‐(4‐Fluorophenoxy)aniline as Anticancer Agents

New 3-O-substituted xanthone derivatives as promising acetylcholinesterase inhibitors

1,2-Dihydroxyxanthone: Effect on A375-C5 Melanoma Cell Growth Associated with Interference with THP-1 Human Macrophage Activity

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