Triethylammonium acetate ionic liquid assisted one-pot synthesis of dihydropyrimidinones and evaluation of their antioxidant and antibacterial activities

Attri, Pankaj; Bhatia, Rohit; Gaur, Jitender; Arora, Bharti; Gupta, Anjali; Kumar, Naresh; Choi, Eun Ha

doi:10.1016/j.arabjc.2014.05.007

Cited by 75 publications

(44 citation statements)

References 42 publications

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“…The enolate of b-ketoester is formed by coordinating the aldehyde with PPh 3 , which helps in the deprotonation of b-ketoester. In 2014, Attri et al utilized triethylammoniumacetae (TEAA) as a catalyst and reaction medium for the synthesis of 3,4-dihydropyrimidinone 20 and its derivatives under solvent free conditions using aldehydes 1, urea/thiourea 2, and b-ketoesters 3 as subtrates [44]. The reaction yield was obtained upto 92%.…”

Section: Synthetic Strategiesmentioning

confidence: 99%

“…10. These compounds were evaluated using disk diffusion assay and zone of inhibition was measured [44]. The assay method involves the pouring of nutrient agar (25 mL) into the petri dishes under aseptic conditions in a laminar flow hood.…”

Section: Antibacterial Activitymentioning

confidence: 99%

“…The antioxidant activity was determined using DPPH (1,1-dipheny-2-picrylhydrazyl) free radical scavenging and (cupric reducing antioxidant capacity) CUPRAC assays. DPPH assay is basically used to determine the free radical scavenging property of antioxidant compounds [44]. Gallic acid and quercitin were used as standard compounds and the working solutions of test extracts and standards were prepared in methanol.…”

Section: Antioxidant Activitymentioning

confidence: 99%

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Recent synthetic and medicinal perspectives of dihydropyrimidinones: A review

Kaur

Chaudhary

Kumar

et al. 2017

European Journal of Medicinal Chemistry

249

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Dihydropyrimidines are the most important heterocyclic ring systems which play an important role in the synthesis of DNA and RNA. Synthetically they were synthesized using Multi-component reactions like Biginelli reaction and Hantzschdihydropyridine. In the past decades, such Biginelli type dihydropyrimidones have received a considerable amount of attention due to the interesting pharmacological properties associated with this heterocyclic scaffold. In this review, we highlight recent developments in this area, with a focus on the DHPMs, recently developed as anti-inflammatory, anti-HIV, anti-tubercular, antifungal anticancer, antibacterial, antifilarial, antihyperglycemic, antihypertensive, analgesic, anti-convulsant, antioxidant, anti-TRPA1, anti-SARS, and anti-cancer activity and α binding affinity.

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Section: Synthetic Strategiesmentioning

confidence: 99%

Section: Antibacterial Activitymentioning

confidence: 99%

Section: Antioxidant Activitymentioning

confidence: 99%

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Recent synthetic and medicinal perspectives of dihydropyrimidinones: A review

Kaur

Chaudhary

Kumar

et al. 2017

European Journal of Medicinal Chemistry

249

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“…The batzelladine alkaloids A and B are used for the treatment of the epidemic, acquired immune deficiency syndrome (AIDS), which inhibited the binding of human immunodeficiency virus envelope protein gp-120 to human CD4 cells to become potential new leads for AIDS therapy [14] . In the past, a broad range of biological effects, including antibacterial [15] , antitubercular [16,17] , antitumor [18] , antiinflammatory [19] , antioxidant [20] and antiamoebic [21] activities have been ascribed to these partly reduced pyrimidine derivatives. Apart from synthetic DHPM derivatives, several marine natural products with fascinating biological activities containing the dihydropyrimidine-5-carboxylate core have been isolated [22] .…”

Section: Research Papermentioning

confidence: 99%

Synthesis and Antimicrobial Activity of Fluorine Containing Pyrazole-clubbed Dihydropyrimidinones

Desai¹,

Vaghani²,

Patel³

et al. 2018

pharmaceutical-sciences

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Desai, et al.: Fluorine Containing Pyrazole-clubbed DihydropyrimidinonesIn the present communication synthesis of pyrazole-containing dihydropyrimidinone motifs (4a-o) and their antimicrobial activity and cytotoxicity were reported. The newly synthesized compounds were characterized using infrared, proton nuclear magnetic resonance, carbon-13 nuclear magnetic resonance and mass spectral techniques. Compounds 4b, 4c, 4f, 4g, 4i and 4j were the most active derivatives identified during antimicrobial activity screening. On the basis of antibacterial activities, it was observed that compounds 4b and 4c exhibited activity against methicillin resistant Staphylococcus aureus with minimum inhibitory concentrations of 12.5 and 6.25 µg/ml, respectively. From structure activity relationship studies, it could be concluded that electron withdrawing groups played a crucial role in enhancing antimicrobial and cytotoxic effects of title compounds. In addition, the results of the cytotoxicity studies indicated that compounds 4b, 4c, 4g and 4j possessed lower levels of cytotoxicity.

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“…Recently, Biginelli reactions 6 have attracted much interest in the synthesis of 3,4-dihydropyrimidin-2-(1H)-one/thione derivatives because of their special pharmaceutical and biological activities. For example, these compounds have found use as calcium channel blockers, α-1a-antagonists, 7 and also as antihypertensive, 8 anticancer, 9 anti-HIV, 10 antibacterial, antifungal, 23 or p-dodecylbenzenesulfonic acid. 24 Some of the limitations of these methodologies include low yields, the use of toxic organic solvents and catalysts, harsh reaction conditions and expensive materials.…”

Section: Introductionmentioning

confidence: 99%

Chromium (III) Nitrate Nonahydrate: An Environmentally Benign and Efficient Heterogeneous Catalyst for Facile One-Pot Biginelli Synthesis of 3,4-Dihydropyrimidin-2-(1H)-One/Thione Derivatives Under Solvent-Free Conditions

2016

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Abstract:The use of chromium(III) nitrate nonahydrate (Cr(NO 3 ) 3 ·9H 2 O) as an efficient, mild and economical catalyst for the one-pot three-component Biginelli synthesis of 3,4-dihydropyrimidin-2-(1H)-one/thione derivatives in the reaction between β-keto esters (methyl or ethyl acetoacetate), aromatic aldehydes (benzaldehye derivatives) and urea or thiourea under thermal and solvent-free conditions with good yields and short reaction times is reported. The most benefits of this synthetic method include the use of an efficient, eco-friendly, inexpensive and non-toxic catalyst, as well as the solvent-free conditions. All products were characterized by 1 H NMR spectroscopy and melting point determination.

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Triethylammonium acetate ionic liquid assisted one-pot synthesis of dihydropyrimidinones and evaluation of their antioxidant and antibacterial activities

Cited by 75 publications

References 42 publications

Recent synthetic and medicinal perspectives of dihydropyrimidinones: A review

Recent synthetic and medicinal perspectives of dihydropyrimidinones: A review

Synthesis and Antimicrobial Activity of Fluorine Containing Pyrazole-clubbed Dihydropyrimidinones

Chromium (III) Nitrate Nonahydrate: An Environmentally Benign and Efficient Heterogeneous Catalyst for Facile One-Pot Biginelli Synthesis of 3,4-Dihydropyrimidin-2-(1H)-One/Thione Derivatives Under Solvent-Free Conditions

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