A Convenient One-Pot Synthesis of 4-Methyl-3-Phenyl-, 3-Aryl- and 3-Aryl-4-Phenylcoumarins

Kamat, Shrivallabh P.; D’Souza, Asha M.; Paknikar, S. K.; Beauchamp, Philip S.

doi:10.3184/030823402103171834

Cited by 16 publications

(8 citation statements)

References 14 publications

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“…3-(4-Chlorophenyl)-2H-chromen-2-one ( 9 ) was prepared from 4-chlorophenylacetic acid using the general procedure described before; 60% yield; mp 190–192 °C (MeOH). The spectral data (IR, 1 H-NMR and 13 C-NMR) were quite comparable with the data reported in reference [ 45 ]. MS (EI) m/z 256 (M + , 55).…”

Section: Methodssupporting

confidence: 86%

“…3-(3,4-Dimethoxyphenyl)-2H-chromen-2-one ( 14 ) Prepared as described in the general procedure from 2-(3,4-dimethoxyphenyl)acetic acid; yield 55%; mp 127–129 °C (MeOH); IR, 1 H-NMR and 13 C-NMR (CDCl 3 ) as described in reference [ 45 ]. MS (EI) m/z 282 (M + , 100).…”

Section: Methodsmentioning

confidence: 99%

“…To this aim, we have used two stably transfected cell lines. The previously described 5.1 cell line [ 45 ] is a Jurkat-derived clone stably transfected with a plasmid containing the luciferase gene under the control of HIV-LTR. In this cell clone, activation with TNFα induces NF- κ B activation and subsequent HIV-1 expression.…”

Section: Methodsmentioning

confidence: 99%

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3-Phenylcoumarins as Inhibitors of HIV-1 Replication

et al. 2012

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We have synthesized fourteen 3-phenylcoumarin derivatives and evaluated their anti-HIV activity. Antiviral activity was assessed on MT-2 cells infected with viral clones carrying the luciferase gene as reporter. Inhibition of HIV transcription and Tat function were tested on cells stably transfected with the HIV-LTR and Tat protein. Six compounds displayed NF-κB inhibition, four resulted Tat antagonists and three of them showed both activities. Three compounds inhibited HIV replication with IC50 values < 25 µM. The antiviral effect of the 4-hydroxycoumarin derivative 19 correlates with its specific inhibition of Tat functions, while compound 8, 3-(2-chlorophenyl)coumarin, seems to act through a mechanism unrelated to the molecular targets considered in this research.

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Section: Methodssupporting

confidence: 86%

Section: Methodsmentioning

confidence: 99%

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3-Phenylcoumarins as Inhibitors of HIV-1 Replication

et al. 2012

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“…To this aim, we have used two stably transfected cell lines. The previously described 5.1 cell line [ 55 ] is a Jurkat-derived clone stably transfected with a plasmid containing the luciferase gene under the control of HIV-LTR. In this cell clone, activation with TNFα induces NF-κB activation and subsequent HIV-1 expression.…”

Section: Methodsmentioning

confidence: 99%

Neoflavonoids as Inhibitors of HIV-1 Replication by Targeting the Tat and NF-κB Pathways

et al. 2017

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Twenty-eight neoflavonoids have been prepared and evaluated in vitro against HIV-1. Antiviral activity was assessed on MT-2 cells infected with viral clones carrying the luciferase reporter gene. Inhibition of HIV transcription and Tat function were tested on cells stably transfected with the HIV-LTR and Tat protein. Seven 4-phenylchromen-2-one derivatives showed HIV transcriptional inhibitory activity but only the phenylchrome-2-one 10 inhibited NF-κB and displayed anti-Tat activity simultaneously. Compounds 10, 14, and 25, inhibited HIV replication in both targets at concentrations <25 μM. The assays of these synthetic 4-phenylchromen-2-ones may aid in the investigation of some aspects of the anti-HIV activity of such compounds and could serve as a scaffold for designing better anti-HIV compounds, which may lead to a potential anti-HIV therapeutic drug.

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“…The preparation of these 8-bromo-6-methyl-3-phenylcoumarins was performed via the classical Perkin reaction. 7,8,34,35,36 This reaction occurs by condensation of the 3-bromo-5-methylsalicylaldehyde 2 and the conveniently substituted phenylacetic acids, with N,N'-dicyclohexylcarbodiimide (DCC) as dehydrating agent, in reflux of DMSO, during 24 hours (scheme 1). The reaction to obtain 3-6 is very clean and the yields are between 45-50%.…”

Section: Compounds 3-5 Don't Present Mao-a Inhibitory Activity For the Highest Concentration Tested (100 µM)mentioning

confidence: 99%

Synthesis and pharmacological evaluation of coumarins as new scaffold on the Parkinson´s disease

Matos

Castelao

Janeiro

et al. 2009

Proceedings of the 13th International Electronic Conference on Synthetic Organic Chemistry

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With the aim to find out the structural features for the MAO inhibitory activity and selectivity, in the present communication we report the design, synthesis and pharmacological evaluation of a new series of 8-bromo-6-methyl-3-phenylcoumarin derivatives without substituent and with different number of methoxy substituent in the 3-phenyl ring. The substituent in this new scaffold was introduced in the 3', 4' and/or 5' positions of the 3-phenyl ring of the coumarin moiety. The synthesized compounds 3-6 were evaluated as MAO A and B inhibitors using R-(-)-deprenyl (selegiline) and Iproniazide as reference inhibitors, showing, most of them, MAO-B inhibitory activities in the nanomolar range. Compounds 3 (11.05±0.81 nM), 4 (3.23±0.49 nM) and 5 (7.12±0.01 nM) show higher activity than selegiline (IC 50 = 19.60 nM), and high MAO-B selectivity with 9,050fold, 30,960-fold and 14,045-fold inhibition levels, with respect to the MAO-A isoform.

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A Convenient One-Pot Synthesis of 4-Methyl-3-Phenyl-, 3-Aryl- and 3-Aryl-4-Phenylcoumarins

Cited by 16 publications

References 14 publications

3-Phenylcoumarins as Inhibitors of HIV-1 Replication

3-Phenylcoumarins as Inhibitors of HIV-1 Replication

Neoflavonoids as Inhibitors of HIV-1 Replication by Targeting the Tat and NF-κB Pathways

Synthesis and pharmacological evaluation of coumarins as new scaffold on the Parkinson´s disease

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