Mono-, bis-, and tris[1-(p-chlorobenzoyl)-5-methoxy-2-methylindole-3-acetyl]glycerides and 1,3-dialkanoyl-2-[1-(p-chlorobenzoyl)-5-methoxy-2-methylindole-3-acetyl]glycerides were synthesized and evaluated for antiinflammatory activity in the rat paw carrageenin edema assay. Three of the most active compounds (4, 18a, and 18e) were tested in the rat adjuvant arthritis model and found to be essentially equivalent in activity to indomethacin. On a molar basis, the acute gastric irritating properties of 18a and 18e were seven to eight times less than indomethacin, resulting in a 2.5- to 3-fold improvement in the ratio of antiedema activity to ulcerogenicity.