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231223s2005 xx ||||| 00| ||eng c |
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|a pubmed24n0510.xml
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|a (DE-627)NLM152874860
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|a (NLM)15625718
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|a DE-627
|b ger
|c DE-627
|e rakwb
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|a eng
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|a Burgueño-Tapia, Eleuterio
|e verfasserin
|4 aut
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|a 1H, 13C and 15N NMR assignments of phenazopyridine derivatives
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|c 2005
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|a Text
|b txt
|2 rdacontent
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|a ohne Hilfsmittel zu benutzen
|b n
|2 rdamedia
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|a Band
|b nc
|2 rdacarrier
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|a Date Completed 11.05.2005
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|a Date Revised 21.11.2013
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|a published: Print
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|a Citation Status MEDLINE
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|a Copyright 2004 John Wiley & Sons, Ltd.
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|a Phenazopyridine hydrochloride (1), a drug in clinical use for many decades, and some derivatives were studied by one- and two-dimensional (1)H, (13)C and (15)N NMR methodology. The assignments, combined with DFT calculations, reveal that the preferred protonation site of the drug is the pyridine ring nitrogen atom. The chemoselective acetylation of phenazopyridine (2) and its influence on the polarization of the azo nitrogen atoms were evidenced by the (15)N NMR spectra. Molecular calculations of the phenazopyridines 2-4 show that the pyridine and phenyl groups are oriented in an antiperiplanar conformation with intramolecular hydrogen bonding between the N-b atom and the C-2 amino group preserving the E-azo stereochemistry
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|a Journal Article
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|a Research Support, Non-U.S. Gov't
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|a Carbon Isotopes
|2 NLM
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|a Nitrogen Isotopes
|2 NLM
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|a Protons
|2 NLM
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|a Phenazopyridine
|2 NLM
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|a K2J09EMJ52
|2 NLM
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|a Mora-Pérez, Yolanda
|e verfasserin
|4 aut
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|a Morales-Ríos, Martha S
|e verfasserin
|4 aut
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|a Joseph-Nathan, Pedro
|e verfasserin
|4 aut
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|i Enthalten in
|t Magnetic resonance in chemistry : MRC
|d 1985
|g 43(2005), 3 vom: 01. März, Seite 256-60
|w (DE-627)NLM098179667
|x 1097-458X
|7 nnns
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|g volume:43
|g year:2005
|g number:3
|g day:01
|g month:03
|g pages:256-60
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|d 43
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|e 3
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|h 256-60
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