Pyrrolo-quinoline derivatives as potential antineoplastic drugs

Novel quinolines carrying pyridine, thienopyridine, isoquinoline, thiazolidine, thiazole and thiophene moieties as potential anticancer agents

“…It has been reported that designing a single molecule with more than one pharmacophore with different modes of action could be beneficial for the treatment of cancer (4), as well as for reducing unwanted side effects (5). Many quinolines, dihydropyridines, thienopyridines, isoquinolines, acrylamides, thiazolidines, thiazoles and thiophenes were found to possess antineoplastic activity (6)(7)(8)(9)(10)(11). Although the antineoplastic activity of these quinolines was attributed to intercalating binding to DNA, there were additional advantages of quinolines that interact with DNA, with a low association constant.…”

Synthesis and characterization of some N‐mannich bases of [1,2,3]triazoloquinolines

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Some novel N-Mannich bases of [1,2,3]-triazolo [4,5-f] and [4,5-h]quinolines were synthesized following the classical experimental procedure for Mannich base preparation: triazoloquinoline with formaldehyde and secondary amine. Tricyclic nuclei were obtained starting from two protected isomeric amino-quinolines, which were nitrated, reduced and diazotated.

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“…In the field of synthesis of substituted pyrroloquinolines as biologically active compounds, our recent good results [1,2] prompted us to continue research, moving towards relatively new, similar polyheterocyclic [1,2,3]triazolo [4,5-f]quinolines, which have been proposed as potential antimicrobial and anticancer drugs [3], due to their isosteric nature in comparison with other known bioactive azoloquinolines [4].…”

“…Our interest in the preparation of some N-Mannich bases of [1,2,3]triazoloquinolines arose from continued studies on the chemical and pharmacological properties of both benzazoles [4] and heterocyclic Mannich bases [5].…”

“…We examined [1,2,3]triazolo [4,5-f]quinoline 6 and [1,2,3]triazolo [4,5-h]quinoline 13, prepared following a well-established method, starting from o-diaminoquinolines 14 and 12 via a diazotization reaction with simultaneous intramolecular cyclization. As primary aryl amine for the synthesis of 19 and 25, we chose an aniline derivative, known on the analogy of our previous compounds showing antiproliferative activity [1,2]. The bioactivity of compounds showing suitable physico-chemical characteristics is being assessed.…”