Synthesis and DNA Binding Properties of γ-Carbolinium Derivatives and Benzologues

Abstract

The 5H-pyrido[4,3-b]indole, 11H-indolo[3,2-c]quinoline, 5H-benzo[f]pyrido[4,3-b]indole, and 13H-benz[5,6]indolo[3,2-c]quinoline heteroaromatic nuclei have been synthesized by the Graebe−Ullmann method by classical heating or under microwave irradiation. These tri-, tetra-, and pentacyclic compounds were transformed into the corresponding cationic derivatives by N-alkylation, and the DNA-binding properties of the resulting cationic systems were examined using UV−vis spectroscopy, viscometric determinations, and molecular modeling techniques. The tetracyclic cations were transformed into bis-salts by means of a diethyl bispiperidine rigid chain and a more flexible polyamide linker, but the low solubility of these bis-salts made the study of their bisintercalating properties difficult.

γ-Carbolines and their hydrogenated derivatives. 1. Aromatic γ-carbolines: methods of synthesis, chemical and biological properties (review)

“…As a rule such transformations take place in the presence of copper or its divalent salts as catalyst [7], but in some cases heating alone is sufficient [8,9]. 25-70% + It is significant that the thermal decomposition of benzotriazoles takes place more smoothly and with better yields in hot syrupy phosphoric, pyrophosphoric (H 4 P 2 O 7 ), and polyphosphoric acids [10] than with zinc chloride, but the role of the acid in this transformation is not at the moment quite clear.…”

“…γ-Carboline is a weak NH acid the anion of which adds at an activated multiple bond (the Michael reaction) [94], and it is also alkylated and acylated by the appropriate reagents [8,95,96]. During the treatment of the γ-carboline anion with O-(mesitylenesulfonyl)hydroxylamine 5-amino-γ-carboline is formed [89].…”

Synthesis, spectroscopic characterization and DFT calculations of a new highly fluorescent heterocyclic system: imidazo[4,5-a]quinindoline

“…On the other hand, indoloquinoline alkaloids have recently received considerable attention due to their promising DNA intercalating 10 and antimalarial properties. [11][12][13] Particularly, indolo [2,3-b]quinolines (also called quinindolines), are a group of synthetic analogues of the natural alkaloid neocryptolepine.…”

The first example of an intramolecular Westphal reaction. Synthesis of a new aza-quinolizinium type system

“…In a current research project focused on the synthesis and biochemistry of novel DNA intercalators based on quinolizinium and aza-quinolizinium chromophores [1][2][3][4], the Westphal reaction [5] has proved to be a useful tool for preparing these polycyclic systems containing a bridgehead quaternary nitrogen. Although the procedure has been described for C-C [5][6][7], N-N [8-1 l] and N-C [12][13][14][15] substrates, it had always being used in its intermolecular version.…”

“…Although the procedure has been described for C-C [5][6][7], N-N [8-1 l] and N-C [12][13][14][15] substrates, it had always being used in its intermolecular version.…”