The present investigation is in the interest of some synthesized novel derivatives 2, 5- disubstituted-3-[5-(1H-indol-3-yl)-4,5-dihydro-1H-pyrazol-3-yl]-6-chloro-2-methyl-4-phenyl-quinoline 4(a-f) and 2, 5 - disubstituted - 3 - [5-(1H-indol-3-yl) - 4, 5-dihydro-1 H- isoxazole - 3 - yl] - 6 - chloro - 2 – methyl - 4 - phenyl - quinoline5 (a-c).The core nucleus indolescaffold is incorporated with different biological active heterocycles such as indole, quinoline, pyrazoline/isoxazoline. The characterization of the synthesisedcompounds reported is based on IR, 1H NMR, 13CNMR and mass spectral data. All the synthesised compounds were screened for their antibacterial activity on four bacteria (two Gram positive Species Bacillus subtilis, Staphylococcus aureus and two Gram negative species, Escherichia coli, Salmonella typhi) and antifungal activity on two fungi species (Aspergillusniger, Aspergillusfumigatus).Ciprofloxacin is used as bacterial standards and Amphotericin B is used as fungal standards for references to evaluate the efficacy of the tested compounds. Amongst the biological evaluated synthesised compounds 4b,4e and 5b exhibited most potent antimicrobial activity.It was observed that the presence of electron withdrawing group at 2and 5 position of indoleremarkably enhanced the antimicrobial activity.