Synthesis of 2-styrylchromones as a novel class of antiproliferative agents targeting carcinoma cells

Shaw, Arthur Y.; Chang, Cheng‐Hsin; Liau, Hao‐Han; Lu, Pei‐Jung; Chen, Huiling; Yang, Chia‐Ning; Li, Hao-Yi

doi:10.1016/j.ejmech.2009.01.034

Cited by 67 publications

(36 citation statements)

References 20 publications

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“…6 0 -Methoxy-2'-hydroxyacetophenone (2b) (4.69 g, 95%) and 4'-methoxy-2'-hydroxyacetophenone (2c) (4.59 g, 93%), which showed spectroscopic and analytical data identical to one previously reported [36]. Methoxyethoxylmethyl chloride (MEMCl) (4.14 mL, 36.3 mmol) was added to a solution of 2 0 ,4'-dihydroxyacetophenone (1c) (33 mmol) in acetone (60 mL) with potassium carbonate (9.12 g, 66 mmol).…”

Section: Synthesis Of Methoxy-2'-hydroxyacetophenones (2b 2c)supporting

confidence: 75%

Novel chromone and xanthone derivatives: Synthesis and ROS/RNS scavenging activities

Proença

Albuquerque

Ribeiro

et al. 2016

European Journal of Medicinal Chemistry

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a b s t r a c tChromones and xanthones are oxygen-containing heterocyclic compounds acknowledged by their antioxidant properties. In an effort to develop novel agents with improved activity, a series of compounds belonging to these chemical classes were prepared. Their syntheses involve the condensation of appropriate 2-methyl-4H-chromen-4-ones, obtained via Baker-Venkataraman rearrangement, with (E)-3-(3,4-dimethoxyphenyl)acrylaldehyde to provide the corresponding 2-[(1E,3E)-4-(3,4-dimethoxyphenyl)buta-1,3-dien-1-yl]-4H-chromen-4-ones. Subsequent electrocyclization and oxidation of these compounds led to the synthesis of 1-aryl-9H-xanthen-9-ones. After cleavage of the protecting groups, hydroxylated chromones and xanthones were assessed as scavenging agents against both reactive oxygen species (ROS) [superoxide radical (O 2 -), hydrogen peroxide (H 2 O 2 ), hypochlorous acid (HOCl), singlet oxygen ( 1 O 2 ), and peroxyl radical (ROO )] and reactive nitrogen species (RNS) [nitric oxide ( NO) and peroxynitrite anion (ONOO À )]. Generally, all the tested new hydroxylated chromones and xanthones exhibited scavenger effects dependent on the concentration, with IC 50 values found in the micromolar range. Some of them were shown to have improved scavenging activity when compared with previously reported analogues, allowing the inference of preliminary conclusions on the structure eactivity relationship.

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Section: Synthesis Of Methoxy-2'-hydroxyacetophenones (2b 2c)supporting

confidence: 75%

Novel chromone and xanthone derivatives: Synthesis and ROS/RNS scavenging activities

Proença

Albuquerque

Ribeiro

et al. 2016

European Journal of Medicinal Chemistry

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Section: Resultsmentioning

confidence: 99%

“…Having 2a, 2b and 2c in hand, the final step was condensation with phenylacetic acid derivatives (3a-g) in the presence of tert-BuOK in dry pyridine to provide the 3-styrylchromone derivatives (4-13) and allyl-protected products of 3-styrylchromones (14-20), respectively. 3-Styrylchromones having the allyloxy group were submitted to a deprotection step, using Pd(PPh 3 ) 4 in the presence of morpholine in degassed anhydrated THF, for removing the allyl group and affording 3-styrylchromones bearing the hydroxyl group (14)(15)(16)(17)(18)(19)(20).Biological Activity All synthesized compounds were evaluated for their 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radical scavenging and α-glucosidase inhibitory activities.As shown in Table 1, modifications of 3-styrylchromones on the chromone ring (A-ring) and the phenyl group (B-ring) of the styryl moiety revealed some interesting structure-activity relationships. As a result, the introduction of the methoxy group or halogen atom (F or Cl) substituent (4-13) on the Bring did not show DPPH radical scavenging activity, while the introduction of the hydroxyl group did.…”

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confidence: 99%

Synthesis and Biological Evaluation of 3-Styrylchromone Derivatives as Free Radical Scavengers and α-Glucosidase Inhibitors

2014

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A series of 3-styrylchromone derivatives (4-20) were synthesized and the structure-activity relationships for α-glucosidase inhibition and antioxidant activities were analyzed. Among the synthesized compounds, compounds 15 and 20, which contain a catechol moiety, showed both potent 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radical scavenging activity (15: EC 50 17 µM; 20: EC 50 23 µM) and α-glucosidase inhibitory activity (15: IC 50 16 µM; 20: IC 50 10 µM). Our data suggest that 3-styrylchromone derivatives are novel α-glucosidase inhibitors that have the potential to counteract diet-induced hyperglycemia in diabetes.Key words 3-styrylchromone; α-glucosidase inhibitor; antioxidant; structure-activity relationship Diabetes mellitus is a metabolic disorder characterized by hyperglycemia resulting from insufficiency of secretion or action of endogenous insulin. α-Glucosidase has been recognized as a therapeutic target for modulation of postprandial hyperglycemia. α-Glycosidase inhibitors act to delay glucose absorption, making them potent drugs to control blood glucose levels.1) On the other hand, antioxidants function as free radical scavengers, chelating agents for pro-oxidant metals, quenchers of singlet oxygen formation, and reducing agents. 2,3)Because of their antioxidant characteristics, antioxidants are important in the prevention of human diseases. The accumulated evidence suggests that diabetic patients are under oxidative stress and that oxidative stress plays a major role in the pathogenesis of diabetes mellitus. 4) Recently, several researchers have evaluated α-glucosidase inhibitors possessing free-radical scavenging activity. 5-11)4H-1-Benzopyran-4-ones (chromones) are an important class of oxygenated heterocyclic compounds, and have attracted the attention of organic chemists and biochemists due to their biological activities and occurrence in natural products. This chromone core structure is found in flavones, isoflavones, and 2-styrylchromones. Flavones and isoflavones are distributed in several species of plants. In contrast, 2-styrylchromones constitute a small group of naturally occurring chromones. Synthetic 2-styrylchromones possess a number of biological activities, including antioxidant, 12,13) anti-allergic, 14) anti-inflammatory, 15) antitumor, [16][17][18] and antiviral [19][20][21] effects. The synthesis and evaluation of biological activities of 2-styrylchromones has been extensively investigated, while studies dealing with 3-styrylchromones are few. Moreover, although there are some examples of the synthesis of 3-styrylchromones, [22][23][24][25][26][27] only a few studies have evaluated the biological activity of 3-styrylchromones. 22,28) In order to further explore novel biological activities, a series of 3-styrylchromone derivatives were synthesized, containing newly prepared compounds, and structure-activity relationships in regards to antioxidant activity and α-glycosidase inhibition were investigated. Results and DiscussionChemistry 3-Styrylchromone derivatives presented in this...

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“…A variety of biological properties have been ascribed to 2-SCs, including antiallergic, [112] anti-inflammatory, [113] antioxidant, [114][115][116][117][118] antitumor [10][11][12]36,39,119] and antiviral, [49,58,66] as well as affinity and selectivity for A 3 adenosine receptors, [38] reviewed by Gomes et al in 2010. [120] Here we update the biological assessment of 2-SCs, but also describe some studies not considered in that review.…”

Section: Biological Properties Of 2-styrylchromonesmentioning

confidence: 99%

“…[32] Condensation between 2-methyl-3-nitrochromones and benzaldehydes in dry methanol at reflux together with a few drops of piperidine afforded the corresponding 3-nitro-2-styrylchromones 22 in 70-80 % yields. [33] A wide range of 2-SCs 23, unsubstituted at C-3, were obtained by condensation between substituted 2-methylchromones and appropriate benzaldehydes in alkaline medium with ethanol as solvent at room temperature, [25,[34][35][36] 55°C [37] or boiling temperature [38] or even in methanol at reflux [39,40] (Scheme 4).…”

Section: Condensation Between 2-methylchromones and Benzaldehydesmentioning

confidence: 99%

An Overview of 2‐Styrylchromones: Natural Occurrence, Synthesis, Reactivity and Biological Properties

Santos

Silva

2017

Eur J Org Chem

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Synthesis of 2-styrylchromones as a novel class of antiproliferative agents targeting carcinoma cells

Cited by 67 publications

References 20 publications

Novel chromone and xanthone derivatives: Synthesis and ROS/RNS scavenging activities

Novel chromone and xanthone derivatives: Synthesis and ROS/RNS scavenging activities

Synthesis and Biological Evaluation of 3-Styrylchromone Derivatives as Free Radical Scavengers and α-Glucosidase Inhibitors

An Overview of 2‐Styrylchromones: Natural Occurrence, Synthesis, Reactivity and Biological Properties

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