University of Khartoum

Synthesis of 2-phenyl- and 2,3- diphenyl-quinolin-4-carboxylic acid derivatives

Synthesis of 2-phenyl- and 2,3- diphenyl-quinolin-4-carboxylic acid derivatives

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Title: Synthesis of 2-phenyl- and 2,3- diphenyl-quinolin-4-carboxylic acid derivatives
Author: Sana Adam, Elhadi
Abstract: Quinoline derivatives are a group of compounds known to possess a wide range of biological activities. The chemistry of quinolines together with their corresponding aldehydes were dealt with in chapter one of this study. Special emphasis was given to the chemistry of benzaldehyde. Twenty five 2-phenyl-and 2,3-diphenyl-quinolin-4-carboxlic acid derivatives together with their corresponding intermediates were prepared in this work. Basically, the synthetic design of these compounds arised from the appropriate disconnections of the target 2-phenyl- and 2,3- diphenyl-quinolin-4-carboxylic acids. The retro synthesis analysis of these compounds reveals pyruvic acid, aromatic amine and benzaldehyde or phenyl pyruvic acid, aromatic amine and benzaldehyde as possible logical precursors for 2-phenyl- and 2,3-diphenyl-quinolin-4-carboxylic acids respectively. The purity and identities of the synthesized compounds were elucidated through chromatographic and spectroscopic techniques. The compounds were heavily subjected to spectroscopic analysis (UV, IR, GC/MS, 1H-and 13C-NMR). The appropriate disconnections and the mechanisms of the corresponding reactions were given and discussed in chapter three. The spectral data were interpreted and correlated with the target structures. The prepared 2-phenyl- and 2,3-diphenyl-quinolin-4-carboxylic acid derivatives were screened for their antibacterial activity. The compounds were tested against the standard bacterial organisms B. subtilis, S. aureus, E. coli and P. vulgaris. Some of these compounds were devoid of antibacterial activity against S. aureus and P. vulgaris, while others showed moderate activity. All of the tested compounds showed an activity against B. subtilis and E. coli. 2,3-diphenyl-6-sulphanilamidoquinolin- 4-carboxylic acid showed the highest activity against the four standard tested organisms.
URI: http://khartoumspace.uofk.edu/handle/123456789/13231
Date: 2015-06-16


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