The reaction of dibenzo[c,e]oxepine-5,7-dione (diphenic anhydride) (1) with different aliphatic and aromatic amines 2-4, 8-10 furnished 2'-[arylcarbamoyl]biphenyl-2-carboxylic acids 5-7, 11, 14 and N2,N2'-diarylbiphenyl-2,2'-dicarboxamide 13. Condensation reaction of 7 with aromatic aldehydes 15, 16 in ethanol resulted in the formation of Schiff base compounds 17, 18. Also, reaction of 7 with ethyl/phenylisothiocyanates 19, 20 in dioxane afforded thiourea derivatives 22, 23. Reaction of 7 with chloroacetylchloride furnished the intermediate chloroacetamide derivative 24 which underwent subsequent cyclization when reacted with malononitrile and potassium thiocynate to afford pyrrole and 4-thiazolidinone compounds 26, 28 respectively. Ten newly synthesized compounds were selected by National Cancer Institute (NCI), USA to be screened for their anticancer activity at a single high dose (10−5 M) against a panel of 60 cancer cell line.