Synthesis of dinitrochalcones by using ultrasonic irradiation in the presence of potassium carbonate

Wang, Wei; Wu, Qing; Ding, Ling; Zhang, Aiqing; Wang, Duoyuan

doi:10.1016/j.ultsonch.2004.12.009

Cited by 20 publications

(5 citation statements)

References 14 publications

(11 reference statements)

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“…The synthesis of chalcones 3a – c with one NO 2 group under standard Claisen–Schmidt conditions provided moderate yields [ 17 , 18 , 19 ]. In the case of dinitro-substituted chalcones 3d , e , the method using ultrasonic irradiation has been shown earlier [ 20 ] to give high yields of the reaction products. According to our research data, the condensation reaction, proceeding in the presence of H 3 BO 3 (the Lewis acid) as the catalyst under reflux in acetic acid for 12 h, allowed us to obtain nitro-chalcones 3d , e in 72–78% yields.…”

Section: Resultsmentioning

confidence: 99%

Amino Derivatives of Diaryl Pyrimidines and Azolopyrimidines as Protective Agents against LPS-Induced Acute Lung Injury

et al. 2023

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The problem of lung damage originating from excessive inflammation and cytokine release during various types of infections remains relevant and stimulates the search for highly effective and safe drugs. The biological activity of the latter may be associated with the regulation of hyperactivation of certain immune cells and enzymes. Here, we propose the design and synthesis of amino derivatives of 4,6- and 5,7-diaryl substituted pyrimidines and [1,2,4]triazolo[1,5-a]pyrimidines as promising double-acting pharmacophores inhibiting IL-6 and NO. The anti-inflammatory activity of 14 target compounds was studied on isolated primary murine macrophages after LPS stimulation. Seven compounds were identified to inhibit the synthesis of nitric oxide and interleukin 6 at a concentration of 100 µM. The most active compounds are micromolar inhibitors of IL-6 secretion and NO synthesis, showing a minimal impact on innate immunity, unlike the reference drug dexamethasone, along with acceptable cytotoxicity. Evaluation in an animal model of acute lung injury proved the protective activity of compound 6e, which was supported by biochemical, cytological and morphological markers.

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Section: Resultsmentioning

confidence: 99%

Amino Derivatives of Diaryl Pyrimidines and Azolopyrimidines as Protective Agents against LPS-Induced Acute Lung Injury

et al. 2023

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“…1-(4-Nitrophenyl)-3-(4-Chlorophenyl)-propenone 3i : mp 171-172°C [36]; 1 H NMR (CDCl 3 , 400 MHz): δ (ppm) 8.32 (2 H, d, J = 9.1 Hz), 8.11 (2 H, d, J = 8.8 Hz), 7.74 (1 H, d, J = 15.8 Hz), 7.59 (2 H, d, J = 8.8 Hz), 7.42 (1 H, d, J = 15.8 Hz), 7.36 (2 H, d, J = 8.8 Hz); 13 C NMR (CDCl 3 , 62.5 Hz): δ (ppm) 187.96, 150.64, 148.97, 142.01, 133.79, 133.19, 130.12, 129.84, 124.29, 121.26.…”

Section: Discussionmentioning

confidence: 99%

New eco-friendly animal bone meal catalysts for preparation of chalcones and aza-Michael adducts

Riadi

Abrouki

Mamouni

et al. 2012

Chemistry Central Journal

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Two efficient reactions were successfully carried out using Animal Bone Meal (ABM) and potassium fluoride or sodium nitrate doped ABMs as new heterogeneous catalysts under very mild conditions. After preparation and characterization of the catalysts, we first report their use in a simple and convenient synthesis of various chalcones by Claisen–Schmidt condensation and then in an aza-Michael addition involving several synthesized chalcones with aromatic amines. All the reactions were carried out at room temperature in methanol; the chalcone synthesis was also achieved in water environment under microwave irradiation. Doping ABM enhances the rate and yield at each reaction. Catalytic activities are discussed and the ability to re-use the ABM is demonstrated.ResultsFor Claisen–Schmidt the use of ABM alone, yields never exceeded 17%. In each entry, KF/ABM and NaNO3/ABM (79-97%) gave higher yields than using ABM alone under thermic condition. Also the reaction proceeded under microwave irradiation in good yields (72-94% for KF/ABM and 81-97% for NaNO3/ABM) and high purity. For aza-Michael addition the use of ABM doped with KF or NaNO3 increased the catalytic activity remarkably. The very high yields could be noted (84-95% for KF/ABM and 81-94% for NaNO3/ABM).ConclusionThe present method is an efficient and selective procedure for the synthesis of chalcones an aza-Michael adducts. The ABM and doped ABMs are a new, inexpensive and attractive solid supports which can contribute to the development of catalytic processes and reduced environmental problems.

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“…The three-step synthesis of amino derivatives of di(hetero)aryl-substituted azolo[1,5a]pyrimidines 7a,b from commercially available reagents is shown in Scheme 2. The interaction of aromatic aldehydes with aromatic ketones results in the formation of the corresponding nitrochalcones 6a,b [27,28]. These nitrochalcones react with aminoazoles to produce nitro derivatives of di(hetero)aryl-substituted azolo[1,5-a]pyrimidines 4c,d.…”

Section: Chemistrymentioning

confidence: 99%

Novel Substituted Azoloazines with Anticoagulant Activity

Spasov,

Fedorova,

Rasputin

et al. 2023

IJMS

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Hypercytokinemia, or cytokine storm, often complicates the treatment of viral and bacterial infections, including COVID-19, leading to the risk of thrombosis. However, the use of currently available direct anticoagulants for the treatment of COVID-19 patients is limited due to safety reasons. Therefore, the development of new anticoagulants remains an urgent task for organic and medicinal chemistry. At the same time, new drugs that combine anticoagulant properties with antiviral or antidiabetic activity could be helpfull in the treatment of COVID-19 patients, especially those suffering from such concomitant diseases as arterial hypertension or diabetes. We have synthesized a number of novel substituted azoloazines, some of which have previously been identified as compounds with pronounced antiviral, antibacterial, antidiabetic, antiaggregant, and anticoagulant activity. Two compounds from the family of 1,2,4-triazolo[1,5-a]pyrimidines have demonstrated anticoagulant activity at a level exceeding or at least comparable with that of dabigatran etexilate as the reference compound. 7,5-Di(2-thienyl)-4,5-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine has shown the highest ability to prolong the thrombin time, surpassing this reference drug by 2.2 times. This compound has also exhibited anticoagulant activity associated with the inhibition of thrombin (factor IIa). Moreover, the anticoagulant effect of this substance becomes enhanced under the conditions of a systemic inflammatory reaction.

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Synthesis of dinitrochalcones by using ultrasonic irradiation in the presence of potassium carbonate

Abstract: The synthesis of dinitrochalcones was studied by using ultrasonic irradiation in the presence of potassium carbonate as a catalyst, which provided a conventional procedure with the advantages of a short reaction period and as high as 90% product yield.

Cited by 20 publications

References 14 publications

Amino Derivatives of Diaryl Pyrimidines and Azolopyrimidines as Protective Agents against LPS-Induced Acute Lung Injury

Amino Derivatives of Diaryl Pyrimidines and Azolopyrimidines as Protective Agents against LPS-Induced Acute Lung Injury

New eco-friendly animal bone meal catalysts for preparation of chalcones and aza-Michael adducts

Novel Substituted Azoloazines with Anticoagulant Activity

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