1H-Imidazol[4,5-c]quinoline derivatives as potential bioactive molecules synthesis and biological evaluation

Mahmoud, Zeinab Mohamed Fahmy Abd ElBaky (2012) 1H-Imidazol[4,5-c]quinoline derivatives as potential bioactive molecules synthesis and biological evaluation. Doctoral (PhD) thesis, Memorial University of Newfoundland.

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Abstract

Imidazoquinolines are interesting heterocyclic systems. They are formed as a result of the fusion between the imidazole five membered ring and quinoline, benzopyridine, system. Different imidazoquinolines can be generated according to the various positions of fusions; at least nine distinct combinations can be identified for this scaffold. Interestingly, diverse biopharmaceutical applications and uses can also be delineated according to each specific imidazoquinoline. Pertinent to these facts, an account on the different synthetic approaches for the possible imidazoquinolines prefaces this thesis. Furthermore, the thesis includes a purposeful survey covering the various biological, pharmaceutical and industrial applications are. More specifically, the lH-imidazo[ 4,5-c ]quinoline nucleus is of significant importance. Many members belonging to this specific nucleus are reported to possess anticancer, antimicrobial and immunomodifing properties. In an attempt to explore further applications for this specific nucleus, two imidazo[ 4,5-c ]quinoline-based projects were launched. The first project explores the effect of the insertion of a sulfur atom on the expected antimicrobial activity. Accordingly, the 2-aryl, 2-acyl-, 2-carbamoyl-, and -azolylmethyl thiosubstitutedimidazo[ 4,5-c ]quinoline derivatives have been synthesized adapting both conventional and microwave techniques. The antimicrobial screening of the target compounds was performed against some representatives of Gram-positive and Gram-negative bacteria. The null in activity was explained through a preliminary in silica study in comparison to the control. Furthermore, the second project was directed towards the synthesis of lHimidazo[ 4,5-c ]quinoline-2-one derivatives as an extension of a previously established quinoline-based project. This recent project was meant to synthesize novel antineoplastic agents but with improved physicochemical properties. Unfortunately, the project was not a fruitful one and had to be discontinued due to many reasons. The most important of these reasons is that the successfully synthesized compounds failed to possess any cytotoxic activity.

Item Type: Thesis (Doctoral (PhD))
URI: http://research.library.mun.ca/id/eprint/11766
Item ID: 11766
Additional Information: Includes bibliographical references (leaves 107-115) -- Restricted until October 2013.
Department(s): Pharmacy, School of
Date: May 2012
Date Type: Submission
Library of Congress Subject Heading: Organic cyclic compounds--Therapeutic use; Organic cyclic compounds--Derivatives--Therapeutic use; Organic cyclic compounds--Synthesis; Bioactive compounds--Synthesis; Organic cyclic compounds--Analysis
Medical Subject Heading: Heterocyclic Compounds with 4 or More Rings--therapeutic use; Heterocyclic Compounds with 4 or More Rings--analysis; Chemistry Techniques, Synthetic

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