Quaternization of N‐Heterocycles with Propylene Oxide and Epichlorohydrin

Vassilev, Aleksey; Dikova, Ivanka; Deligeorgiev, Todor; Drexhage, K. H.

doi:10.1081/scc-200025601

Cited by 11 publications

(2 citation statements)

References 16 publications

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“…Several novel heterocyclic N-2-hydroxypropyl quaternary salts (7,8) have been prepared by the reaction of propylene oxide or epichlorohydrin (6) with the appropriate heterocyclic base (4,5) in the presence of perchloric or hydrobromic acid (Scheme 2) [5]. The quaternisation of different N-heterocycles (9,10) with acrylamide (11) or N-alkyl acrylamide has also been N X + R-I CH 3 CN, reflux 24 h N + X R I -X = S, Se, O, C(CH 3 ) 2, CH=CH; R = C 2 H 5, C 6 H 13, C 10 H 21 described (Scheme 3) [6], resulting in compounds 12 and 13.…”

Section: Intermediates For Styryl Dyesmentioning

confidence: 99%

Styryl dyes – synthesis and applications during the last 15 years

Deligeorgiev

Vasilev

Kaloyanova

et al. 2010

Coloration Technology

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One of the most widely used and important groups of functional dyes are the styryl dyes and a review of this functional dye class has not been published for more than 15 years. In this review article, we describe the new trends in the synthesis of a range of novel intermediates and styryl dyes and include the most interesting examples of their high‐tech applications. However, this review is not intended to be comprehensive because of the large number of styryl dye studies that have been carried out in this time. Styryl cyanine dyes are widely used in optical recording media in laser discs, as flexible dyes, laser dyes, as optical sensitisers and in various other fields, for example dye‐sensitised solar cells and dyes with non‐linear optical properties. Additionally, the most important applications for these dyes are in bio‐labelling and in medicinal analysis.

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Section: Intermediates For Styryl Dyesmentioning

confidence: 99%

Styryl dyes – synthesis and applications during the last 15 years

Deligeorgiev

Vasilev

Kaloyanova

et al. 2010

Coloration Technology

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100

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“…The starting materials 1b and 1c-1e were commercially available and were used as supplied. The intermediates 1a, 2a-2c, 3a and 3b were prepared by our previously published procedure [15,17]. Melting points were determined on a Kofler apparatus and are uncorrected.…”

Section: Synthesismentioning

confidence: 99%

Polycationic Monomeric and Homodimeric Asymmetric Monomethine Cyanine Dyes with Hydroxypropyl Functionality—Strong Affinity Nucleic Acids Binders

et al. 2021

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New analogs of the commercial asymmetric monomethine cyanine dyes thiazole orange (TO) and thiazole orange homodimer (TOTO) with hydroxypropyl functionality were synthesized and their properties in the presence of different nucleic acids were studied. The novel compounds showed strong, micromolar and submicromolar affinities to all examined DNA ds-polynucleotides and poly rA–poly rU. The compounds studied showed selectivity towards GC-DNA base pairs over AT-DNA, which included both binding affinity and a strong fluorescence response. CD titrations showed aggregation along the polynucleotide with well-defined supramolecular chirality. The single dipyridinium-bridged dimer showed intercalation at low dye-DNA/RNA ratios. All new cyanine dyes showed potent micromolar antiproliferative activity against cancer cell lines, making them promising theranostic agents.

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