Synthesis of novel 3,5,6-trisubstituted 2-pyridone derivatives and evaluation for their anti-inflammatory activity

Gonçalves, Davana S.; Melo, Samara Mendes de Souza; Jacomini, Andrey P.; Silva, Michael J. V. da; Pianoski, Karlos Eduardo; Ames, Franciele Queiroz; Aguiar, Rafael Pazinatto; Oliveira, Alisson Felipe; Volpato, Hélito; Bidóia, Danielle Lazarin; Nakamura, Celso V.; Bersani-Amado, Ciomar Aparecida; Back, Davi F.; Moura, Sidnei; Paula, Fávero Reisdorfer; Rosa, Fernanda A.

doi:10.1016/j.bmc.2020.115549

Cited by 16 publications

(18 citation statements)

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“…An interesting approach for preparing the 2‐pyridone core, which was recently disclosed, involves the reaction between β‐enamino diketone 3 and nitriles (Scheme 30). [ 84 ] By using malononitrile (in refluxing EtOH for 6 h), the initial product of the 1,4‐addition followed by cyclization produced a series of 3‐cyano pyridinium salts 84 , at yields of 54–94 % (Scheme 30). Using a linear synthetic methodology, the authors subjected 84 to acidic media (HCl, EtOH, 15 min).…”

Section: Synthesis Of Other Oxa/aza Heterocyclesmentioning

confidence: 99%

“…When 87 was treated with HCl (in a one‐pot procedure), 90 was obtained at 60–71 % (Scheme 30). [ 84 ]…”

Section: Synthesis Of Other Oxa/aza Heterocyclesmentioning

confidence: 99%

“…In the same work, [ 84 ] the anti‐inflammatory activity of compounds 84 – 90 was evaluated, and it was discovered that compound 91 (Figure 4) could selectively inhibit type 2 cyclooxygenase (COX 2). Also, through molecular docking studies, an effective binding of 91 to the site of the type 2 cyclooxygenase was observed.…”

Section: Synthesis Of Other Oxa/aza Heterocyclesmentioning

confidence: 99%

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The Wonderful World of β‐Enamino Diketones Chemistry

et al. 2020

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The simple preparation and functionalization of oxa/aza heterocycles requires new and efficient starting materials to be discovered so that regioselective methodologies with a wide range of applications in organic synthesis can be developed. With this in mind, β‐enamino diketones have emerged as a suitable building block for preparing the most diverse (poly)heterocyclic systems, through cyclocondensation or cycloaddition reactions. This review compiles all the reactions that have been conducted using these starting materials, ever since they were first disclosed in 1980.

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Section: Synthesis Of Other Oxa/aza Heterocyclesmentioning

confidence: 99%

“…When 87 was treated with HCl (in a one‐pot procedure), 90 was obtained at 60–71 % (Scheme 30). [ 84 ]…”

Section: Synthesis Of Other Oxa/aza Heterocyclesmentioning

confidence: 99%

Section: Synthesis Of Other Oxa/aza Heterocyclesmentioning

confidence: 99%

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The Wonderful World of β‐Enamino Diketones Chemistry

et al. 2020

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“…[ 18 ] To overcome the selectivity issue, β‐enamino diketones (see Scheme 1) have emerged as suitable starting materials for the synthesis of several heterocyclic scaffolds, due to presenting high selectivity in most of the cyclocondensation reactions performed. [ 19–21 ] Even though the chemistry of carboxyethyl β‐enamino diketones 1 has been explored, [ 22–29 ] trifluoromethyl 2 ones have been far less used in heterocyclic synthesis. [ 21,30–34 ] Thus, this work aims to study the cyclocondensation reaction between β‐enamino diketones ( CCC building blocks) and 2‐aminobenzimidazole ( NCN ‐dinucleophile), observing the regioselectivity of the obtained products.…”

Section: Introductionmentioning

confidence: 99%

Divergent and Regioselective Synthesis of (Trifluoromethyl/carboxyethyl)benzo[4,5]imidazo[1,2‐a]pyrimidines from β‐Enamino Diketones

et al. 2020

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A divergent and regioselective cyclocondensation reaction of β‐enamino diketones with 2‐aminobenzimidazole is reported. The β‐enamino diketones react with 2‐aminobenzimidazole to form exclusively 1,2‐ or 1,4‐regioisomers of benzo[4,5]imidazo[1,2‐a]pyrimidines, depending on the nature of the EWG group in the diketones: when the diketone has a carboxyethyl group, only the 1,2‐regioisomer was obtained; and when the EWG = CF3, only the 1,4‐regioisomer was isolated. The structure of the obtained products was unambiguously determined by 2D‐NMR experiments and single‐crystal X‐ray analysis.

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“…Notably, differential activation of 5-HT1A receptors has been proposed to be an attractive strategy for the management of several neurological and psychiatric conditions linked to pattern separation such as schizophrenia (Schreiber and Newman-Tancredi, 2014), anxiety , Parkinson's disease (Newman-Tancredi et al, 2018) and cerebral ischemia (Aguiar et al, 2020). Besides, selective activation of 5-HT1A receptors has shown promise results in ameliorating cognitive deficits .…”

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confidence: 99%

The contribution of 5-HT1A receptors in improving plasticity and function of the brain

Aguiar¹

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People interested in the research are advised to contact the author for the final version of the publication, or visit the DOI to the publisher's website.• The final author version and the galley proof are versions of the publication after peer review.• The final published version features the final layout of the paper including the volume, issue and page numbers. Link to publication General rightsCopyright and moral rights for the publications made accessible in the public portal are retained by the authors and/or other copyright owners and it is a condition of accessing publications that users recognise and abide by the legal requirements associated with these rights.• Users may download and print one copy of any publication from the public portal for the purpose of private study or research. • You may not further distribute the material or use it for any profit-making activity or commercial gain • You may freely distribute the URL identifying the publication in the public portal. CONTENTS CHAPTER 1 8 General introduction. CHAPTER 2 23The 5-HT1A receptor as a serotonergic target for neuroprotection in cerebral ischemia.CHAPTER 3 68 Activation of 5-HT1A postsynaptic receptors by NLX-101 results in functional recovery and an increase in neuroplasticity in mice with brain ischemia.CHAPTER 4 100 NLX-101, a biased 5-HT1A receptor agonist, improves pattern separation and stimulates neuroplasticity in aged rats. CHAPTER 5131 Involvement of the type-1 cannabinoid receptor (CB1) in the anti-stress and neuroplastic effects of antidepressants.

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Synthesis of novel 3,5,6-trisubstituted 2-pyridone derivatives and evaluation for their anti-inflammatory activity

Cited by 16 publications

References 47 publications

The Wonderful World of β‐Enamino Diketones Chemistry

The Wonderful World of β‐Enamino Diketones Chemistry

Divergent and Regioselective Synthesis of (Trifluoromethyl/carboxyethyl)benzo[4,5]imidazo[1,2‐a]pyrimidines from β‐Enamino Diketones

The contribution of 5-HT1A receptors in improving plasticity and function of the brain

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