Synthesis and biological evaluation of novel angular fused Pyrrolocoumarins

Abstract

Angular pyrrolocoumarins were synthesized from the reaction of 4-hydroxyindole or 5-hydroxyindole with DMAD and PPh₃ and were tested for anti-inflammatory and antioxidant activity. These compounds significantly inhibited the carrageenin-induced paw edema (60.5%–73.4%) and have important scavenging activity. Although their interaction with the free stable radical DPPH is not high, compound 9 is the most potent (73.4%) in the in vivo experiment. Compound 7 seems to be a potent LOX inhibitor. An attempt was made to correlate the biological results with their structural characteristics and physicochemical parameters.

Keywords::

• Pyrrrolocoumarins
• Hydroxyindoles
• Triphenylphosphine
• Dimethylacetylenedicarboxylate
• Antioxidant activity
• Anti-inflammatory activity

Acknowledgements

The authors gratefully acknowledge support of this work through the program PYTHAGORAS II of EPEAEK II (MIS: 97436/073). We would like also to thank Dr C. Hansch and Biobyte Corp. 201 West 4th Str., Suite 204, Claremont CA California, 91711, USA for free access to C-QSAR programme.

Notes

^†Preliminary communication presented at 12th Panhellenic Pharmacochemistry Symposium, January 27–28, 2006, Patras, Greece, Book of Abstrs., p. 28.