2‐Acetyl‐6‐Methoxynaphthalene

The unique structural features and chemical stabilities of bis(phenyl) tetracarboxamidatodirhodium(III) are reported, and their electronic structures are mapped through XPS, electrochemical, and computational methods. Comparison with the structures of dirhodium(II,II) and dirhodium(II,III) oxidative precursors portrays the diphenyl dirhodium(III) compounds as two squarepyramidal rhodium units that have undergone conrotatory motion in order to optimize metal-ligand bonding. Axial phenyl ligands are severely distorted from their expected Rh-Rh-C linear array. XPS data for this series of dirhodium compounds are consistent with the absence of a rhodium-rhodium bond for the diphenyl dirhodium(III) compounds, and electrochemical measurement shows a single reversible Rh2 6+ /Rh2 7+ redox couple. Notably, they exhibit high thermal stability, and Brønsted acid removal of carboxamidate ligands preceeds the formation of benzene. The ability of a phenyl group to impart unusual stability to rhodium(III) compounds is explained by theoretical analysis of the electronic structure of bis--(phenyl)-tetrakis--(carboxamido)dirhodium(III), and comparison is made with previously reported dinitrosyl dirhodium(III) complexes. Formally, two phenyl radicals in combination with a rhodium-rhodium bond are transformed into two phenyl-rhodium bonds. The severe distortion of phenyl rings from linearity is suggested to result from a long-range interaction between the electrondeficient rhodium and distal oxygen atoms.

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“…The product, 2-methoxynaphthalene, was obtained as a white solid (15.5 mg, 91% yield). Mp: 71−73 °C; lit . 71−73 °C.…”

Section: Methodsmentioning

confidence: 99%

Removal of Metal−Metal Bonding in a Dimetallic Paddlewheel Complex: Molecular and Electronic Structure of Bis(phenyl) Dirhodium(III) Carboxamidate Compounds

et al. 2008

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“…6-MNA (1) required for the synthesis of the prodrugs has been prepared by the reported procedure (20,21). Scheme 1 was employed to synthesize piperazinylalkyl ester prodrugs (4a-5d) of 6-MNA (1).…”

Section: Synthesis Of Piperazinylalkyl Ester Prodrugs Of 6-mnamentioning

confidence: 99%

Potential of Piperazinylalkylester Prodrugs of 6-Methoxy-2-Naphthylacetic Acid (6-MNA) for Percutaneous Drug Delivery

et al. 2014

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Abstract. Piperazinylalkyl ester prodrugs (4a-5d) of 6-methoxy-2-naphthylacetic acid (6-MNA) (1) were synthesized and evaluated in vitro for the purpose of percutaneous drug delivery. These ionizable prodrugs exhibited varying aqueous solubilities and lipophilicities depending on the pH of the medium. The prodrugs (4a-5c) showed higher aqueous solubility and similar lipophilicity at pH 5.0 and lower aqueous solubility and higher lipophilicity at pH 7.4 in comparison to 6-MNA. The chemical and enzymatic hydrolyses of the prodrugs was investigated in aqueous buffer solutions (pH 5.0 and 7.4) and in 80% human serum (pH 7.4) at 37°C. The prodrugs showed moderate chemical stability (t 1/2 =6-60 h) but got readily hydrolyzed enzymatically to 6-MNA with half-life ranging from 10-60 min. In the in vitro permeation study using rat skin, the flux of 6-MNA and the prodrugs was determined in aqueous buffers of pH 5.0 and 7.4. The prodrug (5b) showed 7.9-and 11.2-fold enhancement in skin permeation compared to 6-MNA (1) at pH 5.0 and 7.4, respectively. It was concluded that the parent NSAIDs having favorable pharmacokinetic and pharmacodynamic properties coupled with increased skin permeability of their prodrugs could give better options for the treatment of rheumatic diseases.

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“…Syntheses of 6-MNA salts 6-MNA (1) required for the synthesis of the salts was prepared by the reported procedure (Arsenijevic et al, 1988;Furniss et al, 1996). In this study, some salts of 6-MNA with organic and alkali metal bases have been synthesized.…”

Section: Resultsmentioning

confidence: 99%

“…6-MNA (1) required for the synthesis of the salts was prepared by the reported procedure (Arsenijevic et al, 1988;Furniss et al, 1996). 6-MNA (1) dissolved in dichloromethane and small amount of methanol was added to make the solution clear wherever required and reacted with equimolar amount of the base.…”

Section: Synthesis Of Saltsmentioning

confidence: 99%

Enhanced skin permeation of 6-methoxy-2-naphthylacetic acid by salt formation

et al. 2014

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The aim of this work was to prepare salts of 6-methoxy-2-naphthylacetic acid (6-MNA) to improve its physicochemical properties for percutaneous application. 6-MNA, an active metabolite of non-steroidal anti-inflammatory drug nabumetone has long half life and has the tendency to penetrate well into synovial fluid. The physicochemical properties of 6-MNA salts were investigated by solubility measurements, differential scanning calorimetry (DSC) and infrared (IR). The DSC thermograms and Fourier transform infrared (FT-IR) spectra indicated that 6-MNA formed salts with organic and alkali metal bases. Among the series, salts formed with amine bases (ethanolamine, diethanolamine, triethanolamine and diethylamine) had lower melting points while alkali metal salt (sodium) had higher melting point than 6-MNA. The salts had higher solubilities than 6-MNA as determined in phosphate buffer at pH 5.0 and 7.4. There is no significant difference in partition coefficient (log P) values between salts and 6-MNA at pH 5.0 but, at pH 7.4, the log P values for the salts increased by 4-10 times as compared to 6-MNA. In vitro permeation studies showed that all the salts increased the flux in comparision to 6-MNA, and the ethanolamine salt (1b) was found to be having 7.7 and 9.4 times higher permeability as compared to 6-MNA at pH 5.0 and 7.4, respectively.

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2‐Acetyl‐6‐Methoxynaphthalene

Abstract: 2‐acetyl‐6‐methoxynaphthalene product: 2‐acetyl‐6‐methoxynaphthalene reactant: 2‐Methoxynaphthalene (Matheson, Coleman and Bell)

Cited by 7 publications

References 7 publications

Removal of Metal−Metal Bonding in a Dimetallic Paddlewheel Complex: Molecular and Electronic Structure of Bis(phenyl) Dirhodium(III) Carboxamidate Compounds

Removal of Metal−Metal Bonding in a Dimetallic Paddlewheel Complex: Molecular and Electronic Structure of Bis(phenyl) Dirhodium(III) Carboxamidate Compounds

Potential of Piperazinylalkylester Prodrugs of 6-Methoxy-2-Naphthylacetic Acid (6-MNA) for Percutaneous Drug Delivery

Enhanced skin permeation of 6-methoxy-2-naphthylacetic acid by salt formation

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