Naproxen chemical structure

Figure 22-24. CSP for enantiomeric separation of Naproxen. Chemical structure (left) and a CPK model (right). (Adapted from reference 98, with permission.)...

NSAIDs are of diverse chemical structures salicylates (aspirin, sulphasalazine), indole acetic acids (indomethacin, etodolac), heteroaryl acetic acids (diclofenac), arylpropionic acids (ibuprofen, naproxen), anthranilic acids (mefenamic acid) and enolic acids (piroxicam, meloxicam). 

Fig. 21 Left Chemical structures of (7) (a) (-), and (b) (+)-RTIL synthesized from (-), and (+)-chloromethyl menthyl ether, respectively. (II) (a) (S,5)-NPX-PYR, (b) (S)-(+)-6-methoxy-2-naphthylpropionic acid [naproxen, NPX], (c) 1-hydroxy 2-naphthoic acid, and (d) 6-methoxy-2-naphthalene acetic acid. Right fluorescence decay traces (Lex = 266 nm,A,em > 300 nm) of (5,5)-NPX-PYR in (a) (-)- and (b) (+)-CILs. There is an 10% decrease in lifetime of (5,5)-NPX-PYR in (-l-)-CIL compared to that in (-)-CIL. The lifetime of (5,5)-NPX-PYR in acetonitrile is 3.1 ns in acetonitrile due to intramolecular electron transfer. In the CILs, the lifetime is significantly increased and there is a difference in lifetime in the two solvents. Adapted from [114]...

B. Busqewski, M. El Mouelhi, K. Albert, and E. Bayer, Influence of the Structure of chemically binded C18 phases on HPLC separation in naproxen glucuronide diastreoisomers, J. Liquid Chromatogr., 73 505 (1990). 

A conformational analysis of naproxen anion and monensin sodium has been performed by the use of the /hc couplings. Especially extensive use of these couplings has been made by the authors in the case of the latter compound. They concluded that the conformation of monoensin in solution is very close to that in crystals. Further examples of the application of vicinal proton-carbon couplings in the conformational analysis of compounds include the NMR and quantum-chemical study of the stereochemistry of spiroepoxides obtained by oxidation of (Z)-3-arylidene-l-thioflavan-4-ones performed by Toth et and the elucidation of the structure of isomalyngamides A and B isolated from a collection of the cyanobacterium Lyngbya majuscula from Hawaiian waters by Kan et... 

Buszewski, B. El Mouelhi, M. Albert, K. Bayer, E. Influence of the structure of chemically bonded C18 phases on HPLC separation of naproxen glucuronide diastereoisomers. J.Liq.Chromatogr., 1990,13, 505-524... 

Figure 4.14 Schematic illustration of the principles underlying design of Pirkle-type chiral stationary phases (CSPs). (a) Illustration of the concept of reciprocity a single enantiomer of a racemate which separates well on the CSP shown on the left, when used to produce a second CSP shown at the right, will usually afford separation of the enantiomers of analytes that are structurally similar to the chiral selector of the first CSP. Reproduced from Pirkle et al, J. Org. Chem. 57 (1992), 3854, Copyright (1992), with permission of the American Chemical Society, (b) Two CSPs that exhibit reciprocal behavior, and (c) enantiomeric recognition model for the more stable diastereomeric complex between (S)-naproxen dimethylamide and the Whelk-0-1 (3R,4R) analog. Note that hydrogen atoms bonded to carbons are omitted for clarity. Reproduced from Wolf and Pirkle (2002), Tetrahedron 58, 3597, copyright (2002), with permission from Elsevier.

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