A novel series of selenolo [2, 3-b] tetrahydroquinoline derivatives were synthesized by the reaction of NaSeH with 2-chloro-3-cyano-4-(4-methoxyphenyl)-5, 6, 7, 8-tetrahydroquinoline 2 followed by reactions with chloro acetone, chloro acetonitrile, ethyl chloroacetate and chloro acetamide to yield 9 and 11a-c respectively. Reactions of 11c with acetic anhydride, cyclohexanone and aromatic aldehyde affording derivatives 12-14 respectively. Spectroscopic (IR, 1HNMR, 13CNMR and MS) were confirmed the structure of the synthesized compounds. Compounds 5a-c, 9, 11a-c, 12, 13 and 14 were investigated for their anti-inflammatory and analgesic activities; in addition, the most active compounds were tested for their acute toxicity.