3-(4-CHLOROPHENYL)-1-(2,4-dichlorophenyl)-propen-1-one (1) was prepared and reacted with active methylene compound, ethyl cyanoacetate in the presence of ammonium acetate to give the corresponding pyridine carbonitrile (2). The behavior of compound 2 towards phosphorous pentasulfide, phosphorous oxychloride and some acyclic-sugars has been investigated and afforded compounds 3, 4 and 5a-d, respectively. The thioxo-pyridine carbonitrile (3) reacted with different halo compounds namely: methyl iodide, ethyl chloroacetate, some acyclic sugars to afford 6, 7 and 8a-c, respectively. Treatment of compound 3 with acrylonitrile afforded compound 9. Reaction of the thiosulfanyl 6 with hydrazine hydrate gave the hydrazino derivative 10 while reaction of 7 with the same reagents gave the acid hydrazide 11. Also, compound 4 reacted with different nucleophiles to afford compounds 10, 12-14. Condensation of compound 10 with ethyl acetoacetate, acetyl acetone, acetic anhydride, p-chlorobenzaldehyde afforded compounds 15-18, respectively. Moreover, compound 10 reacted with carbon disulfide to afford compound 19. Finally, condensation of compound 10 with aldehydo-sugar namely: D-glucose gave the corresponding acyclic nucleoside 20. Furthermore, biological evaluation of some prepared compounds has been assessed and some of them revealed promising antimicrobial and antioxidant activity.