الفهرس 
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Abstract
Phosphorus plays a major role in medicinal and natural product chemistry, which is the inspiration for the work presented in this thesis. This thesis work deals with synthesis and biological evaluation of α-aminophosphonates bearing quinoline moiety. The first chapter is reviews the synthesis, properties, reactions and biological applications of α-aminophosphonates , the subject of this thesis. The second chapter discusses efforts made towards the synthesis and use of heterocyclic
with quinoline moiety in the development of a three-component synthesis of biologically important α-aminophosphonates. The third chapter describes the details of the experimental procedures and characterisation data for the novel compounds produced.
I. Synthesis and characterization of α-aminophosphonates:
In this thesis the starting aminophenylaminoquinoline derivatives 3a-c have been synthesized in good yields starting from 4,7 dichloroquinloine and (pphenylenediamine 2a, o-phenylenediamine 2b or m-phenylenediamine 2c) in MeOH or DMF at reflux temperature via SNAr mechanism as depicted in Schemes 1and 2.
Scheme 2
The one pot reaction of 3a-c with different aldehydes 4a-g and triphenylphosphite5 in presence of LiClO4 as a Lewis acid catalyst led to the formation of novel α- aminophosphonate derivatives 6a-g bearing quinoline moiety in good yields as
shown in Scheme 3.
Scheme 4
- C6H5OH All the newly synthesized compounds were characterized by IR, 1H-NMR, and MS spectral analysis and they showed analysis consistent with their structures. II. Biological activity:
i. Antibacterial screening: The newly synthesized compounds were tested in vitro for their antibacterial activity against Gram +ve bacteria (Escherichia coli, Bacillus subtilis and Staphylococcus aureus) and Gram -ve bacteria (Klebsiela spp. and pseudomonas aeruginosa). DMSO was used as a control solvent and Cefotaxim, as a reference drug. After (18- 24) hs. incubation at 37ºC, the zone of inhibition was measured in mm. It should be noted that the free amines 3a-c showed a higher antibacterial activity when compared with the corresponding aminophosphonates 6a-g. Among all tested compounds 3b showed the best antibacterial activity against all tested bacterial strains.
ii. Antitumor activity: Some of the newly synthesized compounds were selected and tested for their preliminary in vitro anticancer activity against two tumor cell lines;MCF-7 (human breast adenocarcinoma cell line) and HepG2 (human hepatocellular carcinoma cell line) using DMSO as a negative control. All tested compounds showed weak antitumor activity.
Conclusion:
New 4-aminophenylaminoquinoline derivatives and their α-aminophosphonates analogues were synthesized and evaluated for their antibacterial and anticancer activities. Some of the tested compounds showed good antimicrobial activity against all tested pathogenic bacterial. However, they showed mild anticancer activity against liver and breast cancer cell line.