What is it about?
The L-phenylalanine methyl ester derivative of dexamethasone derived cortienic acid (DF) was synthesized and its crystal structure characterized by the 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. The local anti-inflammatory activity of DF was evaluated using the croton oil-induced ear oedema test. This derivative achieved maximal inhibition of ear oedema at significantly lower concentration in comparison with dexamethasone.
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Why is it important?
The aim of this study was to synthesize the L-phenylalanine methyl ester derivative of dexamethasone-derived cortienic acid (DF), perform crystallographic analysis of its structure and test the local anti-inflammatory activity of this derivative.
Perspectives
The L-phenylalanine methyl ester derivative of dexamethasone-derived cortienic acid (DF) was synthesized and structurally characterized. This derivative is a potential soft drug with fewer side effects and a better skin retention/permeability ratio than dexamethasone. Its crystal structure was characterized by the X-ray diffraction method. Ring A of the steroid nucleus and the phenyl ring (17β-side chain) are almost planar, rings B and C have a slightly distorted chair conformation and ring D has an envelope conformation. Hydrogen bonds that influence crystal packing of this derivative were identified, i.e., O2–H…O4 (crystallographic a direction), and O3–H…O1 and C29–H…F1 interactions (crystallographic b direction). The local antiinflammatory activity of DF was evaluated by the croton oil-induced ear oedema test. This derivative possesses local anti-inflammatory activity with the maximal inhibition of ear oedema achieved at significantly lower concentration in comparison with dexamethasone.
Research Professor Vesna Jaćević
National Poison Control Centre, Military Medical Academy & Medical Faculty, University of Defence, Belgrade, Sebia
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This page is a summary of: Synthesis, crystal structure and local anti-inflammatory activity of the L-phenylalanine methyl ester derivative of dexamethasone-derived cortienic acid, Journal of the Serbian Chemical Society, January 2015, National Library of Serbia,
DOI: 10.2298/jsc150505067d.
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