Anthracene-Derived Bis-Aminophosphonates: Crystal Structure, In Vitro Antitumor Activity, and Genotoxicity In Vivo

Kraicheva, I.; Vodenicharova, Elitsa; Shivachev, Boris; Nikolova, Rositsa; Kril, A.; Topashka-Ancheva, Margarita; Илиев, Иван; Georgieva, A. I.; Gerasimova, Ts.; Tosheva, T.; Tashev, E.; Tsacheva, Ivelina; Troev, K.

doi:10.1080/10426507.2012.761986

Cited by 11 publications

(13 citation statements)

References 27 publications

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“…In addition, and more importantly, investigation of their biological activity would be of great interest. 35 Through this study, it was also investigated the applicability of the The reactions progressed well at 50 ºC and the desired bis(α-aminophosphonates) were produced in excellent isolated yields (85-96%) (Scheme 1, Table 4). However, 1,2-phenylenediamine and 1,3-phenylenediamine failed to react under similar reaction conditions.…”

Section: Table1 Herementioning

confidence: 99%

Benzimidazolium dicationic ionic liquid as an efficient and reusable catalyst for the synthesis of α-aminophosphonates and bis (α-aminophosphonates) under solvent-free condition

Mirzaei

Hasanpour

Mokaber-Esfahani

2015

Phosphorus, Sulfur, and Silicon and the Related Elements

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Benzimidazolium based on dicationic acidic ionic liquid (AIL)is designed, synthesized, and successfully used as a catalyst for the one-pot synthesis of α-aminophosphonates derivatives. The application of this acidic ionic liquid is studied in a new one-pot method for the synthesis of α-aminophosphonates derivatives under solvent-free conditions. The advantages of this method are the reusability of the catalyst, high conversion, short reaction time, and simple experimental procedure.

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Section: Table1 Herementioning

confidence: 99%

Benzimidazolium dicationic ionic liquid as an efficient and reusable catalyst for the synthesis of α-aminophosphonates and bis (α-aminophosphonates) under solvent-free condition

Mirzaei

Hasanpour

Mokaber-Esfahani

2015

Phosphorus, Sulfur, and Silicon and the Related Elements

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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.…”

Section: Chemistry Novel Homologous Polyphosphoesters Namelymentioning

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%

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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“…9 Bis(α-aminophosphonates) exhibit significant biological activities (Figure 1), compound 1 shows antifungal activity, compound 2 has antioxidant activity, 10 and compound 3 shows optimal antiproliferative activity to human tumoral cells from colon carcinoma. 11 Figure 1. Bis(α-aminophosphonates) having biological activities Bis(α-aminophosphonates) were synthesized from Schiff bases 12 or diamine 9,13,14 under microwave irradiation 10 or with Lewis acid.…”

Section: Introductionmentioning

confidence: 99%

Diastereoselective synthesis of bis(α-aminophosphonates) by lipase catalytic promiscuity

et al. 2019

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Anthracene-Derived Bis-Aminophosphonates: Crystal Structure, In Vitro Antitumor Activity, and Genotoxicity In Vivo

Cited by 11 publications

References 27 publications

Benzimidazolium dicationic ionic liquid as an efficient and reusable catalyst for the synthesis of α-aminophosphonates and bis (α-aminophosphonates) under solvent-free condition

Benzimidazolium dicationic ionic liquid as an efficient and reusable catalyst for the synthesis of α-aminophosphonates and bis (α-aminophosphonates) under solvent-free condition

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

Diastereoselective synthesis of bis(α-aminophosphonates) by lipase catalytic promiscuity

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