Coumarin sulfonates: As potential leads for ROS inhibition

Coumarin sulfonates 4-43 were synthesized by reacting 3-hydroxy coumarin 1, 4-hydroxy coumarin 2 and 6-hydroxy coumarin 3 with different substituted sulfonyl chlorides and subjected to evaluate for their in vitro immunomodulatory potential. The compounds were investigated for their effect on oxidative burst activity of zymosan stimulated whole blood phagocytes using a luminol enhanced chemiluminescence technique. Ibuprofen was used as standard drug (IC50 = 54.2 +/- 9.2 mu M). Eleven compounds 6 (IC50 = 46.60 +/- 14.6 mu M), 8 (IC50 = 11.50 +/- 6.5 mu M), 15 (IC50 = 21.40 +/- 12.2 mu M), 19 (IC50 = 5.75 +/- 0.86 mu M), 22 (IC50 = 10.27 +/- 1.06 mu M), 23 (IC50 = 33.09 +/- 5.61 mu M), 24 (IC50 = 4.93 +/- 0.58 mu M), 25 (IC50 = 21.96 +/- 14.74 mu M), 29 (IC50 = 12.47 +/- 9.2 mu M), 35 (IC50 = 20.20 +/- 13.4 mu M) and 37 (IC50 = 14.47 +/- 5.02 mu M) out of forty demonstrated their potential suppressive effect on production of reactive oxygen species (ROS) as compared to ibuprofen. All the synthetic derivatives 4-43 were characterized by different available spectroscopic techniques such as H-1 NMR, C-13 NMR, EIMS and HRMS. CHN analysis was also performed. (C) 2016 Elsevier Inc. All rights reserved.