Inhibitory activity of prostaglandin E2 production by the synthetic 2′-hydroxychalcone analogues: Synthesis and SAR study

Tran, Thanh-Dao; Park, Haeil; Kim, Hyun Pyo; Ecker, Gerhard F.; Thai, Khac-Minh

doi:10.1016/j.bmcl.2009.02.001

Cited by 43 publications

(24 citation statements)

References 24 publications

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“…The phase and baseline were corrected with the TopSpin software (version 3.2 Bruker BioSpin). NMR assignments are based on 1 H, 13 …”

Section: Chemicalsmentioning

confidence: 99%

“…The 2'-hydroxy-3,4,5-trimethoxychalcone ( Figure 1) has shown in vitro inhibitory effects on PGE2 (prostaglandin E2) production from RAW 264.7 cells induced by LPS (lipopolysaccharide). 13 At 10 μM 2'-hydroxychalcones proved strong effect to inhibit the PGE2 production (102.3%). However, these compounds also indicated the effect on cell viability with potential for anti-inflammation and anticancer activity.…”

Section: Introductionmentioning

confidence: 96%

“…12 Thus, the correct structural determination and the knowledge about three-dimensional (3D) atomic structure of chalcones are crucial to understand their properties. In this context, the complete assignments of 13 C nuclear magnetic resonance (NMR) chemical shifts for chalcones, even using computation methodology, can help in identifying the chemical structures of new chalcone derivatives. The 2'-hydroxy-3,4,5-trimethoxychalcone ( Figure 1) has shown in vitro inhibitory effects on PGE2 (prostaglandin E2) production from RAW 264.7 cells induced by LPS (lipopolysaccharide).…”

Section: Introductionmentioning

confidence: 99%

“…However, these compounds also indicated the effect on cell viability with potential for anti-inflammation and anticancer activity. 13 Our research group has worked with quantum mechanics using computational tools to better understand the interpretation of the 13 C NMR chemical shift experimental data. Recently, we published the applicability of the empirical equations for conversion of quantum mechanically calculated chemical shielding tensors into chemical shift values.…”

Section: Introductionmentioning

confidence: 99%

“…Recently, we published the applicability of the empirical equations for conversion of quantum mechanically calculated chemical shielding tensors into chemical shift values. [14][15][16] In these papers, it was pointed out the importance of a linear conversion formula in order to achieve great 13 C NMR chemical shift experimental data reproduction and prediction. In this context, the goal of this work was to investigate the ability of the scaling factor protocol at the GIAO-mPW1PW91/6-31G(d)//mPW1PW91/6-31G(d) level of theory to predict the 13 …”

Section: Introductionmentioning

confidence: 99%

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Conformational Analysis, Experimental and GIAO-DFT 13C NMR Chemical Shift Calculation on 2’-Hydroxy-3,4,5-trimethoxy-chalcone

Costa

Gomes

Silva

et al. 2017

J. Braz. Chem. Soc.

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In this paper we investigated the ability of the GIAO-mPW1PW91/6-31G(d)//mPW1PW91/6-31G(d) level of theory to predict the 13 C nuclear magnetic resonance (NMR) chemical shifts of the 2'-hydroxy-3,4,5-trimethoxy-chalcone molecule. Two different approaches were used. First: the absolute shieldings σ for all carbon atoms in each geometrically optimized conformers of the 2'-hydroxy-3,4,5-trimethoxy-chalcone molecule were calculated at the GIAO-mPW1PW91/6-31G(d)// mPW1PW91/6-31G(d) level of theory. This approach is further used to generate weighted average values for each atom considering the previously obtained conformational distribution. Second: only the σ for the lowest energetic conformer will be taken to account. The robustness of the method was evaluated for two other chalcones: (E)-1-(4-hydroxy-3-methoxyphenyl)-3-(3,5-di-tert-butyl-4-hydroxyphenyl)prop-2-en-1-one and (E)-1-(4-aminophenyl)-3-(3,4-dimethoxyphenyl)prop-2-en-1-one, corroborating the ability of the method in chemical shift prevision. Although, both approaches were able to reproduce the chemical shifts of the 2'-hydroxy-3,4,5-trimethoxy-chalcone, significant differences in the calculated values for C-4 and methoxy carbons were observed. The best results were obtained using the second approach (II).

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“…The phase and baseline were corrected with the TopSpin software (version 3.2 Bruker BioSpin). NMR assignments are based on 1 H, 13 …”

Section: Chemicalsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 96%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Conformational Analysis, Experimental and GIAO-DFT 13C NMR Chemical Shift Calculation on 2’-Hydroxy-3,4,5-trimethoxy-chalcone

Costa

Gomes

Silva

et al. 2017

J. Braz. Chem. Soc.

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Synthesis and Biological Evaluation of Novel Chalcone and Pyrazoline Derivatives Bearing Substituted Vanillin Nucleus

Patel

Bhadani

Bhatt

et al. 2014

Journal of Heterocyclic Chem

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A series of novel chalcone 4a, 4b, 4c, 4d, 4e, 4f, 4g, 4h, 4i, 4j, 4k, 4l and pyrazoline 5a, 5b, 5c, 5d, 5e, 5f, 5g, 5h, 5i, 5j, 5k, 5l derivatives have been synthesized as potential antibacterial agents. The pyrazoline derivatives 5a, 5b, 5c, 5d, 5e, 5f, 5g, 5h, 5i, 5j, 5k, 5l have been synthesized by reaction of various chalcones 4a, 4b, 4c, 4d, 4e, 4f, 4g, 4h, 4i, 4j, 4k, 4l with hydrazine hydrate in the presence of acetic acid. The chalcones 4a, 4b, 4c, 4d, 4e, 4f, 4g, 4h, 4i, 4j, 4k, 4l were prepared by the condensation of key aldehyde 3 with appropriate acetophenone using basic condition and ethanol as a solvent. The key aldehyde 3 has been synthesized by reacting 2‐(chloromethyl)‐3‐methyl‐4‐(2,2,2‐trifluoroethoxy)pyridine hydrochloride and vanillin. The structures of the new compounds were established on the basis of 1H‐NMR, mass, IR, and elemental analysis data. All the newly synthesized compounds were screened for their antibacterial activity against Escherichia coli, Salmonella typhi (Gram‐negative bacteria), Staphylococcus aureus, Micrococcus luteus (Gram‐positive bacteria) and antifungal activity against Candida albicans (fungi).

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¹H and ¹³C NMR spectral assignments of 2′‐hydroxychalcones

Yong

Ahn

Hwang

et al. 2013

Magnetic Reson in Chemistry

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Chalcones are of interest to medicinal chemists because their structures can be easily modified with various functional groups. The syntheses and biological activities of chalcones from natural sources are well known. In this study, 24 2'-hydroxychalcones bearing methoxy substituents were synthesized, among which five are new. The NMR data for all synthesized chalcones are described for the first time. The complete assignments of the (1)H and (13)C NMR data can be used for the identification of newly discovered and widely isolated, synthesized chalcones.

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Inhibitory activity of prostaglandin E2 production by the synthetic 2′-hydroxychalcone analogues: Synthesis and SAR study

Cited by 43 publications

References 24 publications

Conformational Analysis, Experimental and GIAO-DFT 13C NMR Chemical Shift Calculation on 2’-Hydroxy-3,4,5-trimethoxy-chalcone

Conformational Analysis, Experimental and GIAO-DFT 13C NMR Chemical Shift Calculation on 2’-Hydroxy-3,4,5-trimethoxy-chalcone

Synthesis and Biological Evaluation of Novel Chalcone and Pyrazoline Derivatives Bearing Substituted Vanillin Nucleus

¹H and ¹³C NMR spectral assignments of 2′‐hydroxychalcones

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Inhibitory activity of prostaglandin E2 production by the synthetic 2′-hydroxychalcone analogues: Synthesis and SAR study

Cited by 43 publications

References 24 publications

Conformational Analysis, Experimental and GIAO-DFT 13C NMR Chemical Shift Calculation on 2’-Hydroxy-3,4,5-trimethoxy-chalcone

Conformational Analysis, Experimental and GIAO-DFT 13C NMR Chemical Shift Calculation on 2’-Hydroxy-3,4,5-trimethoxy-chalcone

Synthesis and Biological Evaluation of Novel Chalcone and Pyrazoline Derivatives Bearing Substituted Vanillin Nucleus

1H and 13C NMR spectral assignments of 2′‐hydroxychalcones

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¹H and ¹³C NMR spectral assignments of 2′‐hydroxychalcones