Journal of the Serbian Chemical Society 2015 Volume 80, Issue 12, Pages: 1481-1488
https://doi.org/10.2298/JSC150505067D
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Synthesis, crystal structure and local anti-inflammatory activity of the L-phenylalanine methyl ester derivative of dexamethasone-derived cortienic acid
Dobričić Vladimir (University of Belgrade, Faculty of Pharmacy, Belgrade, Serbia)
Francuski Bojana M. (University of Belgrade, Vinča Institute of Nuclear Sciences, Laboratory of Theoretical Physics and Condensed Matter Physics, Belgrade, Serbia)
Jaćević Vesna (University of Defense, Military Medical Academy, Medical Faculty, National Poison Control Centre, Belgrade, Serbia)
Rodić Marko V. (University of Novi Sad, Faculty of Sciences, Novi Sad, Serbia)
Vladimirov Sote (University of Belgrade, Faculty of Pharmacy, Belgrade, Serbia)
Čudina Olivera (University of Belgrade, Faculty of Pharmacy, Belgrade, Serbia)
Francuski Djordje (University of Belgrade, Institute of Molecular Genetics and Genetic Engineering, Belgrade, Serbia)
L-phenylalanine methyl ester derivative of dexamethasone - derived cortienic
acid (DF) was synthesized and its crystal structure was characterized by
X-ray diffraction method. The crystal system is orthorhombic with space
group P212121 and cell constants a = 8.2969 (3) Å, b = 18.9358 (8) Å, c =
20.0904 (6) Å, V = 3156.4 (2) Å3 and Z = 4. Ring A of the steroid nucleus
and phenyl ring in the 17β-side chain are almost planar. Rings B and C have
a slightly distorted chair conformation, whereas ring D has an envelope
conformation. The packing of DF is characterized by a network of
intermolecular hydrogen bonds involving the O4 atom from one side of the
steroid nucleus and O1 and F1 atoms from the other side as hydrogen bond
acceptors. Apart from the intermolecular hydrogen bonds in the crystal
packing, there are also numerous intramolecular hydrogen bonds of the
N-H...O, C-H...O and C-H...F type. Local anti-inflammatory activity of DF
was evaluated by use of croton oil-induced ear edema test. This derivative
achieved maximal inhibition of ear edema at significantly lower
concentration in comparison with dexamethasone.
Keywords: 17β-carboxamide steroids, X-ray diffraction, biological activity, ear edema test
Projekat Ministarstva nauke
Republike Srbije, br. 172041, 172014 i 172035