Synthesis and antiviral bioactivity of novel chalcone derivatives containing purine moiety

Wang, Yanjiao; Zhou, Dagui; He, Fangcheng; Chen, Jixiang; Chen, Yongzhong; Gan, Xiuhai; Hu, Deyu; Song, Baoan

doi:10.1016/j.cclet.2017.07.006

Cited by 27 publications

(16 citation statements)

References 20 publications

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“…The synthetic route of the target compounds is depicted in Scheme 1. Oseltamivir was reacted with the corresponding sulfonyl chlorides to obtain 3a – 3k [18,25,26]. The nitro fragment of 3i – 3k was reduced to amino by iron powder to afford intermediates 5i – 5k .…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Biological Evaluation of NH2-Sulfonyl Oseltamivir Analogues as Influenza Neuraminidase Inhibitors

Chen

Lei

et al. 2019

Molecules

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A series of NH2-sulfonyl oseltamivir analogues were designed, synthesized, and their inhibitory activities against neuraminidase from H5N1 subtype evaluated. The results indicated that the IC50 value of compound 4a, an oseltamivir analogue via methyl sulfonylation of C5-NH2, was 3.50 μM. Molecular docking simulations suggested that 4a retained most of the interactions formed by oseltamivir carboxylate moieties and formed an additional hydrogen bond with the methylsulfonyl group. Meanwhile, 4a showed high stability towards human liver microsomes. More importantly, 4a without basic moieties is not a zwitterion as reported on the general structure of neuraminidase inhibitors. This research will provide valuable reference for the research of new types of neuraminidase inhibitors.

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Section: Resultsmentioning

confidence: 99%

Synthesis and Biological Evaluation of NH2-Sulfonyl Oseltamivir Analogues as Influenza Neuraminidase Inhibitors

Chen

Lei

et al. 2019

Molecules

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“…Chalcones are essential intermediates in the synthetic pathways of flavonoids; they possess a wide variety of therapeutic activities and can also serve as versatile starting materials for various complex molecules in medicinal chemistry [14]. Recent studies have shown that chalcones exhibit a wide variety of biological activities against cancer [15,16], bacteria [17], fungi [18], and viruses [19]. They also exhibit antioxidant [20], anti-depressant [21], and anti-inflammatory [22] activities, and can potentially reduce resistance to various chemotherapeutic agents [23].…”

Section: Introductionmentioning

confidence: 99%

Novel Nitrogen-Based Chalcone Analogs Provoke Substantial Apoptosis in HER2-Positive Human Breast Cancer Cells via JNK and ERK1/ERK2 Signaling Pathways

Rizeq

Gupta

Kheraldine

et al. 2021

IJMS

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Natural chalcones possess antitumor properties and play a role as inducers of apoptosis, antioxidants and cytotoxic compounds. We recently reported that novel nitrogen chalcone-based compounds, which were generated in our lab, have specific effects on triple-negative breast cancer cells. However, the outcome of these two new compounds on human epidermal growth factor receptor 2 (HER2)-positive breast cancer remains nascent. Thus, we herein investigated the effects of these compounds (DK-13 and DK-14) on two HER2-positive breast cancer cell lines, SKBR3 and ZR75. Our data revealed that these compounds inhibit cell proliferation, deregulate cell-cycle progression and significantly induce cell apoptosis in both cell lines. Furthermore, the two chalcone compounds cause a significant reduction in the cell invasion ability of SKBR3 and ZR75 cancer cells. In parallel, we found that DK-13 and DK-14 inhibit colony formation of both cell lines in comparison to their matched controls. On the other hand, we noticed that these two compounds can inhibit angiogenesis in the chorioallantoic membrane model. The molecular pathway analysis of chalcone compounds exposed cells revealed that these compounds inhibit the expression of both JNK1/2/3 and ERK1/2, the major plausible molecular pathways behind these events. Our findings implicate that DK-13 and DK-14 possess effective chemotherapeutic outcomes against HER2-positive breast cancer via the ERK1/2 and JNK1/2/3 signaling pathways.

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“…22 Purine derivatives also demonstrate good activities in regulating plant growth 23,24 and antiplant virus. 25,26 In our previous work, we found that benzenesulfonamide chalcone derivatives containing purine moiety (Figure 2) showed moderate antiviral activity and could be considered as a scaffold for the discovery of novel antiviral agents. 27 However, these compounds lack satisfactory and broad-spectrum antiviral activities.…”

Section: ■ Introductionmentioning

confidence: 99%

“…Some purine drugs have been extensively used in medicine as antiviral agents, such as ganciclovir and abacavir . Purine derivatives also demonstrate good activities in regulating plant growth , and antiplant virus. , …”

Section: Introductionmentioning

confidence: 99%

Synthesis, Antiviral Activity, and Mechanisms of Purine Nucleoside Derivatives Containing a Sulfonamide Moiety

Shi

Wang

et al. 2019

J. Agric. Food Chem.

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Novel purine nucleoside derivatives containing a sulfonamide moiety were prepared, as well as their antiviral activities against potato virus Y (PVY), cucumber mosaic virus (CMV), and tobacco mosaic virus (TMV) were evaluated. The antiviral mechanisms of the compounds were investigated. Results showed that most of the compounds had good antiviral activities. Compound 5 at 500 μg/mL exhibited excellent curative and protective activities of 52.5% and 60.0% and of 52.0% and 60.2% for PVY and CMV, respectively, which are higher than those of ningnanmycin (48.1%, 49.6%; 45.3%, 47.7%), ribavirin (38.3%, 48.2%; 40.8%, 45.5%), and chitosan oligosaccharide (32.5%, 33.8%; 35.1%, 34.6%). Moreover, compound 5 displayed good inactivating activity against TMV, with an EC50 value of 48.8 μg/mL, which is better than that of ningnanmycin (84.7 μg/mL), ribavirin (150.4 μg/mL), and chitosan oligosaccharide (521.3 μg/mL). The excellent antiviral activity of compound 5 is related to its immune induction effect which can regulate the physiological and biochemical processes in plants, including defense-related enzyme activities, defense-related genes, and photosynthesis-related proteins. These results indicate that purine nucleoside derivatives containing a sulfonamide moiety are worthy of further research and development as new antiviral agents.

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Synthesis and antiviral bioactivity of novel chalcone derivatives containing purine moiety

Cited by 27 publications

References 20 publications

Synthesis and Biological Evaluation of NH2-Sulfonyl Oseltamivir Analogues as Influenza Neuraminidase Inhibitors

Synthesis and Biological Evaluation of NH2-Sulfonyl Oseltamivir Analogues as Influenza Neuraminidase Inhibitors

Novel Nitrogen-Based Chalcone Analogs Provoke Substantial Apoptosis in HER2-Positive Human Breast Cancer Cells via JNK and ERK1/ERK2 Signaling Pathways

Synthesis, Antiviral Activity, and Mechanisms of Purine Nucleoside Derivatives Containing a Sulfonamide Moiety

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