Microwave assisted synthesis and X-ray structure of a novel anthracene-derived aminophosphonate. Enantioseparation of two α-aminophosphonates and genotoxicity in vivo

Kraicheva, I.; Tsacheva, Ivelina; Nikolova, Rositsa; Topashka-Ancheva, Margarita; Stoineva, Ivanka; Shivachev, Boris

doi:10.1080/10426507.2016.1247086

Cited by 9 publications

(11 citation statements)

References 22 publications

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“…Recently, we described the synthesis and the in vitro antitumor activity against a panel of human epithelial cancer cell lines and the in vitro and in vivo safety evaluation of anthracene-derived low-molecular and polymeric aminophosphonates and their precursors [20,[25][26][27][28]: Schiff bases S-1 and S-2, α-aminophosphonates A-3-A-6, bis-aminophosphonate B-6 (R, S diastereomer), and polyphosphoesters P-8-P-11, containing aminophosphonate units ( Figure 1). e α-aminophosphonates A-3 and A-4 [25] and the polyphosphoesters P-8-P-11 [20] have been synthesized from the anthracene-derived Schiff base S-1, while the compounds A-5 [25] and A-6 [28] have been prepared using the anthracene-and furan-containing Schiff base S-2. e racemic compound A-5 has been separated into its two enantiomers A-5a and A-5b by HPLC technique [28].…”

Section: Chemistry Novel Homologous Polyphosphoesters Namelymentioning

confidence: 99%

“…e α-aminophosphonates A-3 and A-4 [25] and the polyphosphoesters P-8-P-11 [20] have been synthesized from the anthracene-derived Schiff base S-1, while the compounds A-5 [25] and A-6 [28] have been prepared using the anthracene-and furan-containing Schiff base S-2. e racemic compound A-5 has been separated into its two enantiomers A-5a and A-5b by HPLC technique [28]. Among the studied compounds A-3-A-5, aminophosphonate A-5, bearing anthracene and furan ring, showed the best antitumor effects against all tested human epithelial cancer cell lines.…”

Section: Chemistry Novel Homologous Polyphosphoesters Namelymentioning

confidence: 99%

“…S-1 and S-2. 9-Anthrylidene-p-toluidine S-1 [25,29] and 9-anthrylidene-furfurylamine S-2 [25,28] were prepared following previously described procedures.…”

Section: Synthesis Dimethyl H-phosphonate (Sigma-aldrichmentioning

confidence: 99%

“…xyphosphonyl)-1-(9-anthryl)]-p-toluidine A-3 [25], [N-methyl(diethoxyphosphonyl)-1-(9-anthryl)]-p-toluidine A-4 [25], [N-methyl(diethoxyphosphonyl)-1-(9-anthryl)] furfurylamine A-5 [25], and [N-methyl(dimethoxyphosphonyl)-1-(9-anthryl)]furfurylamine A-6 [28] were obtained according to procedures described earlier. A-5a and A-5b. e enantioseparation of the racemic α-aminophosphonate A-5 into its enantiomers A-5a and A-5b was reported in a previous paper [28] A-5a, e polymers P-8-P-11 were obtained through an addition reaction of poly(oxyethylene H-phosphonate)s to the Schiff base S-1 using synthetic procedures reported previously [20].…”

Section: α-Aminophosphonates A-3-a-6 N-methyl(dimetho-mentioning

confidence: 99%

“…Low-molecular and polymeric aminophosphonates, synthesized earlier [20,[25][26][27][28], were also studied against the same tumor cell lines.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of Two Novel Homologous Polyphosphoesters Containing Aminophosphonate Units and Cytotoxicity of Some Low-Molecular and Polymeric Aminophosphonate Derivatives

Kraicheva

Momekov

Mihaylova

et al. 2018

Advances in Materials Science and Engineering

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Two novel polyphosphoesters containing anthracene- and furan-derived aminophosphonate moieties, namely, poly[oxyethylene(aminophosphonate-co-H-phosphonate)]s P-12 and P-13, were synthesized through an addition of poly(oxyethylene H-phosphonate) to 9-anthrylidene-furfurylamine and characterized. The novel polyphosphoester P-12 and a series of previously described anthracene-derived compounds including Schiff bases S-1 and S-2, α-aminophosphonates A-3–A-6, bis-aminophosphonate B-6, two enantiomers A-5a and A-5b, and polyphosphoesters P-8–P-11 containing aminophosphonate units were screened for antitumor activity against a panel of human leukemic cell lines, using cisplatin as a reference cytotoxic agent. As concluded from the cytotoxicity assays, both precursors S-1 and S-2 presented similar cytotoxicity profiles that are cisplatin-like only in the REH cell line. Leader compound of the α-aminophosphonates is A-4 with cell death-inducing properties fully equaling those of the referent drug in all of the screened leukemic cell lines with the only exception being the AML histological subtype HL-60. Some of the polymeric analogues elicited moderate (P-10 and P-12) to low (P-11) cytotoxic activity, whereas the polyphosphoesters P-8 and P-9 produced in vitro antitumor effects largely surpassing cisplatin’s. The compounds P-8, P-9, and A-4 could be potential new materials for anticancer therapeutic purposed.

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Section: Chemistry Novel Homologous Polyphosphoesters Namelymentioning

confidence: 99%

Section: Chemistry Novel Homologous Polyphosphoesters Namelymentioning

confidence: 99%

“…S-1 and S-2. 9-Anthrylidene-p-toluidine S-1 [25,29] and 9-anthrylidene-furfurylamine S-2 [25,28] were prepared following previously described procedures.…”

Section: Synthesis Dimethyl H-phosphonate (Sigma-aldrichmentioning

confidence: 99%

Section: α-Aminophosphonates A-3-a-6 N-methyl(dimetho-mentioning

confidence: 99%

“…Low-molecular and polymeric aminophosphonates, synthesized earlier [20,[25][26][27][28], were also studied against the same tumor cell lines.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of Two Novel Homologous Polyphosphoesters Containing Aminophosphonate Units and Cytotoxicity of Some Low-Molecular and Polymeric Aminophosphonate Derivatives

Kraicheva

Momekov

Mihaylova

et al. 2018

Advances in Materials Science and Engineering

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Synthesis, Theoretical, in Silico and in Vitro Biological Evaluation Studies of New Thiosemicarbazones as Enzyme Inhibitors

Erdoğan,

Serdar Çavuş,

Muğlu

et al. 2023

Chemistry & Biodiversity

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Eleven new thiosemicarbazone derivatives (1‐11) were designed from nine different biologically and pharmacologically important isothiocyanate derivatives containing functional groups such as fluorine, chlorine, methoxy, methyl, and nitro at various positions of the phenyl ring, in addition to the benzyl unit in the molecular skeletal structure. First, their substituted‐thiosemicarbazide derivatives were synthesized from the treatment of isothiocyanate with hydrazine to synthesize the designed compounds. Through a one‐step easy synthesis and an eco‐friendly process, the designed compounds were synthesized with yields of up to 95% from the treatment of the thiosemicarbazides with aldehyde derivatives having methoxy and hydroxyl groups. The structures of the synthesized molecules were elucidated with elemental analysis and FT–IR, 1H NMR, and 13C NMR spectroscopic methods. The electronic and spectroscopic properties of the compounds were determined by the DFT calculations performed at the B3LYP/6‐311++G(2d,2p) level of theory, and the experimental findings were supported. They exhibited a highly potent inhibition effect on acetylcholinesterase (AChE) and carbonic anhydrases (hCAs) (KI values are in the range of 23.54±4.34 to 185.90±26.16 nM, 103.90±23.49 to 325.90 ±77.99 nM, and 86.15±18.58 to 287.70±43.09 nM for AChE, hCA I, and hCA II, respectively). Furthermore, molecular docking simulations were performed to explain each enzyme‐ligand complex's interaction.

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An Overview of Microwave‐Assisted Kabachnik‐Fields Reactions

et al. 2020

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A comprehensive evaluation of MW-assisted Kabachnik-Fields reactions (phospha-Mannich condensation) is done to draw the attention of synthetic chemists towards a greener, solvent-free and catalyst-free protocol. The review encompasses the diverse class of α-aminophosphonates and its derivatives synthesized via one-pot three component KF reaction, which finds application in various disciplines of chemistry and covers literature up to 2020.

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Microwave assisted synthesis and X-ray structure of a novel anthracene-derived aminophosphonate. Enantioseparation of two α-aminophosphonates and genotoxicity in vivo

Cited by 9 publications

References 22 publications

Synthesis of Two Novel Homologous Polyphosphoesters Containing Aminophosphonate Units and Cytotoxicity of Some Low-Molecular and Polymeric Aminophosphonate Derivatives

Synthesis of Two Novel Homologous Polyphosphoesters Containing Aminophosphonate Units and Cytotoxicity of Some Low-Molecular and Polymeric Aminophosphonate Derivatives

Synthesis, Theoretical, in Silico and in Vitro Biological Evaluation Studies of New Thiosemicarbazones as Enzyme Inhibitors

An Overview of Microwave‐Assisted Kabachnik‐Fields Reactions

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