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Abstract This thesis comprises four chapters. The first one is an introduction which consists of a brief survey on the different methods to synthesize quinoline containing compounds and their anticancer activity, in addition to antimicrobial activity. The second chapter deals with the aim of the work and Schemes that have been carried out to obtain the new required quinoline derivatives. The third chapter clarifies the theoretical discussion of the experimental work for the preparation of the new enamine compounds IIIa-e. Amide compounds IVa-d formed from reaction of the acid chloride derivatives which resulted from IIIc&d in situ with different aromatic amines. Cyclization of compounds IIIa-e to quinoline derivatives VIa-d in boilied diphenylether was done and then subjected to chlorination to give the key 4-chloro quinoline intermediates VIIa-d. Reaction of compounds VIIa&d with hydrazine hydrate or phenyl hydrazine resulted in formation of pyrazolo quinoline derivatives VIII and IXa&b. In addition to the synthesis of the target 4-aminoquinoline compounds Xa-l by reaction of VIIa-d with different aromatic amines. Hydrolysis of diethyl-8-bromo-4-(p-substitutedamino)quinoline-3,6-dicarboxylate Xg-Xi by sodium hydroxide resulted in formation of 8-bromo-4-(p-substitutedamino)quinoline-3,6-dicarboxylic acid compounds XIa-c. Claisen –Schmidt condensation of diethyl 4-((4-acetylphenyl)amino)-8-bromoquinoline-3,6-dicarboxylate (Xk) with different aromatic aldehydes gave chalcones XIIa-c. In addition to formation of (E)-diethyl 8-bromo-4-((4-(1-(2-(2- cyanoacetyl)hydrazono)ethyl)phenyl)amino) quinoline-3,6-dicarboxylate (XV) from its reaction with cyanaceticacidhydrazide XIV. Reaction of diethyl 8- bromo-4-((4-(ethoxycarbonyl)phenyl)amino)quinoline-3,6-dicarboxylate Xl with hydrazine hydrate gave the hydrazide derivative XVII, which react with 4-nitrobenzaldehyde and ethylisothiocynate giving compounds XIX and XVIII respectively. O-alkylation of compound Xh named as diethyl 8-bromo-4-((4-hydroxyphenyl)amino)quinoline-3,6-dicarboxylate yielded diethyl 8-bromo-4-((4-(2-ethoxy-2-oxoethoxy)phenyl)amino)quinoline-3,6-dicarboxylate(XX) which hydrolyzed to a tricarboxylic quinoline compound that named 8-bromo-4-((4-(carboxymethoxy)phenyl)amino)quinoline-3,6-dicarboxylic acid XXI. The structure elucidation of the new compounds was supported by elemental analyses, IR, 1H NMR, 13C NMR in addition to mass spectral data. Also, a brief account on the docking study was explained through the binding conformations in comparison with the cytotoxic results. Additionally, theoretical discussion of biological anticancer and antimicrobial screening was given. The fourth chapter consists of the experimental part of this work which contains the detailed procedures used for the synthesis of the new starting materials IIIa-e, VIa-c and VIIa-d and the target quinoline compounds VIII, IXa&b, Xa-l, XIIa-c, XV, XVII, XVIII, XIX, XX and XXI . In addition, data obtained from the element and spectral analyses as well as their physical properties are given in this chapter. It also sheds the light on the anticancer and antimicrobial activities of most of newly synthesized derivatives compared with doxorubicin and erlotinib as standards cytotoxic agent and gentamicin, cefotaxime , ampicillin , fluconazole and tioconazole. Compound XIIa exhibited the highest cytotoxic activity with IC50 1.88, 3.15 and 1.22 μM against used three cell lines, in addition to compound XIIc which showed the highest antimicrobial activity. This chapter also clarifies the correlation between the results of molecular docking and the anticancer activity.