Steady state and time resolved fluorescence studies of new indolizine derivatives with phenanthroline skeleton

Airinei, Anton; Tigoianu, Radu; Danac, Ramona; Matarneh, Cristina M. Al; Isac, Dragoş Lucian

doi:10.1016/j.jlumin.2018.03.005

Cited by 21 publications

(15 citation statements)

References 21 publications

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“…Pyrrolo [1,2-a]quinoline and pyrrolo[2,1-a]isoquinoline cores were generated through [3 + 2] cycloaddition reactions that lead to the formation of in situ (iso)quinolinium ylides [24][25][26][27]. Initially, for the introduction of a 4-substituted phenacyl substituent, salts 3a-c and 5a-c were synthesized by the direct N-alkylation of isoquinoline and quinoline, respectively, using para-substituted 2-bromoacetophenones 2a-c (Schemes 1 and 2) [28].…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Biological Screening of New Cyano-Substituted Pyrrole Fused (Iso)Quinoline Derivatives

et al. 2021

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Several new cyano-substituted derivatives with pyrrolo[1,2-a]quinoline and pyrrolo[2,1-a]isoquinoline scaffolds were synthesized by the [3 + 2] cycloaddition of (iso)quinolinium ylides to fumaronitrile. The cycloimmonium ylides reacted in situ as 1,3-dipoles with fumaronitrile to selectively form distinct final compounds, depending on the structure of the (iso)quinolinium salt. Eleven compounds were evaluated for their anticancer activity against a panel of 60 human cancer cell lines. The most potent compound 9a showed a broad spectrum of antiproliferative activity against cancer cell lines representing leukemia, melanoma and cancer of lung, colon, central nervous system, ovary, kidney, breast and prostate cancer. In vitro assays and molecular docking revealed tubulin interaction properties of compound 9a.

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Section: Resultsmentioning

confidence: 99%

Synthesis and Biological Screening of New Cyano-Substituted Pyrrole Fused (Iso)Quinoline Derivatives

et al. 2021

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“…As a continuation of our dedicated research focused on phenanthrolines fused systems [27][28][29][30] and as part of our concern in the field of biologically active compounds, [31][32][33][34][35] the purpose of our present study was to synthesize new 1,10phenanthroline derivatives having one of its N-atoms locked in order to ensure a potential bio-activity (by maintaining the rings coplanarity and reducing the toxicity due to N-atoms internal chelating propensity). Thus, we report herein the synthesis, structure, fluorescence and the in vitro antimicrobial evaluation of several new 1,10-phenanthroline derivatives.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and properties of new fused pyrrolo-1,10-phenanthroline type derivatives

et al. 2021

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New fused pyrrolo-phenanthroline type derivatives were synthesized, in two steps, from 1,10-phenanthroline and evaluated for antimicrobial activity and fluorescence properties. Our synthetic approach involved a 3+2 dipolar-cycloaddition of some selected N-substituted 1,10-phenanthrolin-1-ium ylides, (m)ethoxycarbonyl and cyano (1,2-di)substituted acetylenes and alkenes, respectively. The structures of compounds were supported by analytical and spectroscopic data. Molecular structures of four compounds have also been also determined by monocrystal XRD analyses. All synthesized compounds were then evaluated for their potential antimicrobial activity against Staphylococcus aureus ATCC25923, Escherichia coli ATCC25922 and Candida albicans ATCC10231. Two of the compounds demonstrated good activity against the above tested strains.

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“…Phenanthrolines are versatile moieties which have found use in many applications [1][2][3] due to a wide variety of interesting properties (complexation [1][2][3], luminescence [1,2,4], biological activities [4][5][6][7], semiconductors [8][9][10]). These polycyclic compounds are also naturally occurring in morphine alkaloids, sterols or hormones [11], which makes the phenanthroline scaffold an excellent choice in the generation of unique bioactive compounds.…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis, Molecular Modelling and Anticancer Activities of New Fused Phenanthrolines

et al. 2020

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Three series of fused pyrrolophenanthroline derivatives were designed as analogues of phenstatin and synthesized in two steps starting with 1,7-phenanthroline, 4,7-phenanthroline and 1,10-phenanthroline, respectively. Two (Compounds 8a and 11c) of the four compounds tested against a panel of sixty human cancer cell lines of the National Cancer Institute (NCI) exhibited significant growth inhibition activity on several cell lines. Compound 11c showed a broad spectrum in terms of antiproliferative efficacy with GI50 values in the range of 0.296 to 250 μM. Molecular docking studies indicated that Compounds 8a and 11c are accommodated in the colchicine binding site of tubulin in two different ways.

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Steady state and time resolved fluorescence studies of new indolizine derivatives with phenanthroline skeleton

Cited by 21 publications

References 21 publications

Synthesis and Biological Screening of New Cyano-Substituted Pyrrole Fused (Iso)Quinoline Derivatives

Synthesis and Biological Screening of New Cyano-Substituted Pyrrole Fused (Iso)Quinoline Derivatives

Synthesis and properties of new fused pyrrolo-1,10-phenanthroline type derivatives

Design, Synthesis, Molecular Modelling and Anticancer Activities of New Fused Phenanthrolines

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