Series of new 1-{N-(2,4-dichlorobenzyl)indolyl)}-1-phenylpropanones were synthesized. The intermediate 1Hindolyl- 1-phenylpropenones were synthesized by the reaction of 3-acetyl indole with appropriate benzaldehyde in the presence of aqueous sodium hydroxide solution under reflux condition. Thus, the prepared intermediate indolyl chalcones has been subsequently treated with 2,4-dichlorobenzyl chloride in the presence of potassium carbonate and DMF as solvent under reflux condition to afford title compounds in good yield. The structures of intermediate and newly synthesized N-(2,4 dichlorobenzyl)- indolylchalcones were confirmed by physical and spectral analysis. All the N-(2,4 dichlorobenzyl)- indolylchalcones were evaluated for antibacterial and antifungal activities. Selected N-(2,4 dichlorobenzyl)- indolylchalcones showed good to excellent antibacterial and antifungal activities with reference to the well-established standards.