In the present study a series of novel Schiff bases which containing the Phenothiazine nucleus were synthesized (PD-1 to PD-10) by the condensation of the compounds N-methyl-10H-phenothiazine-3-carbaldehyde and different acylhydrazides in methanol and glacial acetic acid. All the synthesized compounds have been characterized by using elemental analysis, FT-IR, 1H NMR, 13C NMR spectroscopy and further supported by mass spectroscopy. Purity of all the compounds has been checked on thin layer chromatographic plate and HPLC technique. All the synthesized compounds were tested for their invitro antibacterial and antioxidant activities by agar diffusion plate method and DPPH free radical scavenging assay methods. All the synthesized compounds exhibited significant to moderate antibacterial and antioxidant activities. The results revealed that compound PD-7 exhibited significant antioxidant activity and the compounds PD-2, PD-5 and PD-8 exhibited good activity against S.aureus, E.coli, P. aeruginosa and B.subtilis and moderate activity against K. pneumonia. These compounds can be further exploited to get the potent lead compounds. The detailed synthesis and the antimicrobial screening of the new compounds are reported.