Novel aminated benzimidazo[1,2-a]quinolines as potential fluorescent probes for DNA detection: Microwave-assisted synthesis, spectroscopic characterization and crystal structure determination

Perin, Nataša; Hranjec, Marijana; Pavlović, Gordána; Karminski‐Zamola, Grace

doi:10.1016/j.dyepig.2011.02.003

Cited by 28 publications

(5 citation statements)

References 39 publications

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“…The incorporation of the benzimidazole nuclei with another heteroaromatic skeleton is an important synthetic strategy in drug discovery and can lead to highly conjugated, planar benzannulated benzimidazoles, which have the ability to intercalate between adjacent DNA base pairs. High fluorescence intensity and possibility of interaction with important biomacromolecules of the living systems offer also their potential use as a fluorescent probes for detection of biological important molecules as DNA or different proteins in biomedicinal diagnostics [10,11]. Moreover, quinolines as a one of the most important groups of nitrogen heterocycles, are important structural units widely existing in natural alkaloids, therapeutics and synthetic analogues with wide range of biological activities and have a great importance in the natural, medicinal and environmental sciences.…”

Section: Introductionmentioning

confidence: 99%

Amino substituted benzimidazo[1,2- a ]quinolines: Antiproliferative potency, 3D QSAR study and DNA binding properties

Perin

Nhili

Cindrić

et al. 2016

European Journal of Medicinal Chemistry

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We describe the synthesis, 3D-derived quantitative structure-activity relationship (QSAR), antiproliferative activity and DNA binding properties of a series of 2-amino, 5-amino and 2,5-diamino substituted benzimidazo[1,2-a]quinolines prepared by environmentally friendly uncatalyzed microwave assisted amination. The antiproliferative activities were assessed in vitro against colon, lung and breast carcinoma cell lines; activities ranged from submicromolar to micromolar. The strongest antiproliferative activity was demonstrated by 2-amino-substituted analogues, whereas 5-amino and or 2,5-diamino substituted derivatives resulted in much less activity. Derivatives bearing 4-methyl- or 3,5-dimethyl-1-piperazinyl substituents emerged as the most active. DNA binding properties and the mode of interaction of chosen substituted benzimidazo[1,2-a]quinolines prepared herein were studied using melting temperature studies, a series of spectroscopic studies (UV/Visible, fluorescence, and circular dichroism), and biochemical experiments (topoisomerase I-mediated DNA relaxation and DNase I footprinting experiments). Both compound 36 and its bis-quaternary iodide salt 37 intercalate between adjacent base pairs of the DNA helix while compound 33 presented a very weak topoisomerase I poisoning activity. A 3D-QSAR analysis was performed to identify hydrogen bonding properties, hydrophobicity, molecular flexibility and distribution of hydrophobic regions as these molecular properties had the highest impact on the antiproliferative activity against the three cell lines.

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Section: Introductionmentioning

confidence: 99%

Amino substituted benzimidazo[1,2- a ]quinolines: Antiproliferative potency, 3D QSAR study and DNA binding properties

Perin

Nhili

Cindrić

et al. 2016

European Journal of Medicinal Chemistry

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“…An intense absorption band was noted at 355 nm for precursor 126 while compound 127 showed several absorption bands, especially intense in the region from 250 to 280 nm with high extinction coefficients. Most of these electronic transitions are made from п to п* orbitals of tetracyclic conjugated p‐system and the bathochromic shift was observed for substituted polycyclic benzimidazole system …”

Section: Photophysical Applicationmentioning

confidence: 99%

Polycyclic Benzimidazole: Synthesis and Photophysical Properties

Manna¹,

Das

Samanta³

2019

ChemistrySelect

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Benzimidazole has tremendous application in medicinal chemistry and material science. The fusion of ring/substitution to benzimidazole nucleus produce polycyclic benzimidazole e. g., pyrido[1,2‐a]benzimidazole, benzimidazo[1,2‐a]quinoline, pyrrolo[1,2‐c]benzimidazolequinones (PBIs) and benzimidazo[2,1‐a]isoquinolines and these are the important synthetic strategies in drug discovery. Benzimidazole analogues have versatile therapeutic properties which encouraged the researchers to develop new therapeutic agents. Hence, the synthetic literature survey towards the polycyclic benzimidazole is paramount important. Due to the beautiful fluorescent properties of fused benzimidazole moiety, they are also used in optoelectronics, optical lasers, and organic luminophores. In addition, this scaffold has broad applications in organometallic catalysis, co‐ordination chemistry, and asymmetric catalysis. Herein, we report a vast synthetic route of benzimidazole embedded polyhetrocycles in the last eight years and their photophysical application in the modern research field.

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“…Compared to the BH approach, metal-free C–N coupling reactions have been sparingly reported in the literature. , More prevalent reports of metal-free aminations include microwave irradiation motifs ,− or base-catalyzed reaction schemes. − For example, microwave irradiation has been shown to enable direct metal-free coupling of morpholine to an aromatic ring containing free −OH and −NH 2 substituents ( i.e ., strong electron-donating groups) . In addition, microwaves have been utilized to react aryl halide compounds containing a wide range of substituents.…”

Section: Introductionmentioning

confidence: 99%

Substituent Effects and the Energetics of Noncatalyzed Aryl Halide Aminations: A Theoretical Investigation

et al. 2021

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We report the influence of substituents and physical conditions on activation energies for the noncatalyzed amination (C–N cross-coupling reactions) of aryl halides. We uncover a significant correlation between the barrier heights of the C–N bond formation and Hammett σ parametersa formal measure of the electron-withdrawing or -donating ability of substituents on the aryl halides. Our results indicate that such correlations are useful predictive tools for the amination of aryl halides over a wide range of substituent types. From 54 cases studied (six substituents occupying specific positions relative to halogen atoms), the 2-COOHPhI + NH2 n Pr amination reaction is predicted to possess the lowest noncatalyzed activation free energy (135.6 kJ mol–1) using the B3LYP method. The lower barriers for the 2-COOHPhX (for X = Cl, Br, and I) compounds are shown to originate from collusion between steric and electronic effectsspecifically, the momentary formation of a hydrogen bond between an oxygen site on the ortho-COOH and the lone pair of the entering amine. Internal reaction coordinate (IRC) path calculations afforded us these and other key insights into the nature of the reactions. The control exerted by substituents on the arrangement of the transition state structure, as well as the sensitivity of the reaction barriers to temperature and solvent polarity, are discussed. These results offer new perspectives from which to assess the nature of the C–N bond formation and suggest new avenues for future exploration, especially in progress toward the metal-free amination of aryl compounds.

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Novel aminated benzimidazo[1,2-a]quinolines as potential fluorescent probes for DNA detection: Microwave-assisted synthesis, spectroscopic characterization and crystal structure determination

Cited by 28 publications

References 39 publications

Amino substituted benzimidazo[1,2- a ]quinolines: Antiproliferative potency, 3D QSAR study and DNA binding properties

Amino substituted benzimidazo[1,2- a ]quinolines: Antiproliferative potency, 3D QSAR study and DNA binding properties

Polycyclic Benzimidazole: Synthesis and Photophysical Properties

Substituent Effects and the Energetics of Noncatalyzed Aryl Halide Aminations: A Theoretical Investigation

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