1985
DOI: 10.1107/s0108270185003626
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Structure of naproxen, C14H14O3

Abstract: Abstract. An effective inhibitor of cyclo-oxygenase. Mr=230.25 , monoclinic, P21, a= 13.3150(10), b = 5.7765 (4), c= 7.8732 (4)A, fl= 93.88 (1) °, V= 604.2 (1)A 3, Z= 2, Din= 1.25 (2) (flotation), D~= 1.265 Mg m -3, 2(Mo Ka 1) = 0.70926/~, #(Mo Ka) = 0.095 mm -1, F(000) = 244, T= 296 K, final R(F) = 0.061 for 1037 observed reflections. The rotation of the carboxyl group with respect to the benezene ring, which seems to be connected with anti-inflammatory potential, is similar to the other two substituted propi… Show more

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Cited by 52 publications
(48 citation statements)
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“…The carboxylic acid group of NA does not interact with allyl-terguride at all, and its orientation corresponds to the minimum energy of 2-arylpropionic acids, 37 which is generally found in the crystal structures of free profens. 38,39 This statement is verified by a found torsion angle of C(37)-C(38)-C(43)-C(45) of 64°( for atom numbering see Scheme 1), a value very close to the theoretical one, which is 60°. Since -interaction does not involve chiral groups of allyl-terguride or naproxen, it should be considered as equal for both enantiomers (S)-and (R)-naproxen without exerting stereoselective discrimination.…”
Section: Results and Discussion X-ray Studysupporting
confidence: 70%
“…The carboxylic acid group of NA does not interact with allyl-terguride at all, and its orientation corresponds to the minimum energy of 2-arylpropionic acids, 37 which is generally found in the crystal structures of free profens. 38,39 This statement is verified by a found torsion angle of C(37)-C(38)-C(43)-C(45) of 64°( for atom numbering see Scheme 1), a value very close to the theoretical one, which is 60°. Since -interaction does not involve chiral groups of allyl-terguride or naproxen, it should be considered as equal for both enantiomers (S)-and (R)-naproxen without exerting stereoselective discrimination.…”
Section: Results and Discussion X-ray Studysupporting
confidence: 70%
“…The distances and angles in the naproxen ion in the title compound are similar to those found in naproxen itself, C14H1403, (II) (Ravikumar, Rajan, Pattabhi & Gabe, 1985). The methoxy group is nearly coplanar with the naphthalene moiety in both crystal structures.…”
supporting
confidence: 56%
“…It was suggested that the crystal structure of NPX was broken down by ternary complex formation, and that NPX was monomerized by an interaction with g-CD which had newly emerged. 31 The peak of the FBP molecules in the ternary complex was similar to that in FBP crystal (Fig. 3a), for example, a chemical shift of 183.9 ppm for the carbonyl carbon ''a.''…”
Section: Molecular State Of Guest Drugs In Npx/(fbp/g-cd) Ternary Commentioning
confidence: 75%