Journal article
Dynamic H-1-NMR conformational study in a series of pyridinium Pyrazoles
Revista de chimie (Bucuresti), Vol.58(5), pp.442-446
01 May 2007
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Abstract
The energetic barrier that characterizes the rotation of the pyrazole ring about the N+(sp(2))-C(sp(2)) bond in a series of 1-(pyrazol-3-yl)-2,6-dialkyl-4-phenyl(methyl)-pyridinium derivatives (alkyl = Me, Et, n-Pr, i-Pr) was evaluated by variable temperature dynamic IH-NMR spectroscopy. The rotational motion is restricted by the substitution pattern of the pyridinium ring. The alkyl groups promote specific molecular conformations, with the i-Pr increasing with about 15 kJ/mol the free activation energy for the internal rotation as compared to the case of Et and i-Pr as pyridinium substituents in 2- and 6- positions. The compounds investigated in this study are biological effective as carbonic anhydrase activators, their potency being highly influenced by the capacity of the enzyme active site to accommodate a particular conformation of these molecules. Therefore, an accurate evaluation of the activation parameters favoring a pertinent conformation to suit the general "key-lock" principle could be important for the rational design of derivatives with potential pharmaceutical applications.
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Details
- Title
- Dynamic H-1-NMR conformational study in a series of pyridinium Pyrazoles
- Creators
- Monica IliesMiron Teodor Caproiu
- Publication Details
- Revista de chimie (Bucuresti), Vol.58(5), pp.442-446
- Publisher
- Chiminform Data S A
- Number of pages
- 5
- Resource Type
- Journal article
- Language
- English
- Academic Unit
- Chemistry
- Identifiers
- 991020545123104721
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- Collaboration types
- Domestic collaboration
- International collaboration
- Web of Science research areas
- Chemistry, Multidisciplinary
- Engineering, Chemical