Synthesis and characterization of cyclotriphosphazene derivatives bearing azole groups

Uslu, Aylin; Özcan, Elif; Dural, Sevilay; Yüksel, Fatma

doi:10.1016/j.poly.2016.06.009

Cited by 15 publications

(9 citation statements)

References 33 publications

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“…All of the synthesized compounds are thermally stable and water-soluble. The structures of the derived compounds (4,5,7,8) are shown in Figure 1.…”

Section: Resultsmentioning

confidence: 99%

“…The biological activities of phosphazene derivatives are also at the target of current research due to their medicinal applications in the therapy of microbial, fungal and oncological diseases [3]- [7]. In this, special attention should be again given to cyclophosphazene ring carrying various groups of atoms, since they demonstrate antitumor features [8], [9]. The cytotoxicity of cyclotriphosphazenes against blood, lung, cervix, larynx, colon, bladder, prostate, and breast cancer cell lines have been shown in many studies [9]- [13].…”

Section: Introductionmentioning

confidence: 99%

“…Elemental analysis and the percentage yields of compounds(4,5,7,8).…”

mentioning

confidence: 99%

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NMR and DSC studies on the reactions of pentanedioxy spiro-ansa cyclochlorotriphosphazene and pentanedioxy triple-bridged cylochlorotriphosphazene with monofunctional nucleophiles

Gurbanov

Tuna

Ture

2019

Sakarya University Journal of Science

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In this study, the reactions of 2-(2-hydroxyethyl) thiophene (2) and benzyl alcohol (3) with pentanedioxycyclochlorotriphosphazene (1) and pentanedioxy triple-bridged cylochlorotriphosphazene (6) were studied. The novel cyclotriphosphazene compounds: two di-substituted spiro-ansa, N3P3[O(CH2)5O]-(C6H7OS)]2 (4) and N3P3[O(CH2)5O-(C6H5CH2O)]2 (5); and two fully substituted triple-bridged, N3P3[O(CH2)5O]3-(C6H7OS)6N3P3 (7) and N3P3[O(CH2)5O]3-(C6H5CH2O)6N3P3 (8) derivatives were formed in THF solvent by using NaH base at ambient conditions. Because of their variety of applications, there is a great deal of interest in the preparation of aromatic macrocyclic derivatives of cyclophosphazenes. The main purpose of these studies is to develop bioactive cyclophosphazene derivatives in the search for new effective drug candidates for the treatment of various diseases, in particular, anticancer and antimicrobials. The synthesized compounds (4, 5, 7, 8) were defined using analytical techniques namely Element analysis, TLC/MS system, and NMR spectroscopy. Thermal stabilities, crystal purity, and recrystallization properties and corresponding enthalpies of synthesized derivatives were analyzed in the course of heating and cooling cycles of DSC.

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“…All of the synthesized compounds are thermally stable and water-soluble. The structures of the derived compounds (4,5,7,8) are shown in Figure 1.…”

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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NMR and DSC studies on the reactions of pentanedioxy spiro-ansa cyclochlorotriphosphazene and pentanedioxy triple-bridged cylochlorotriphosphazene with monofunctional nucleophiles

Gurbanov

Tuna

Ture

2019

Sakarya University Journal of Science

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“…Nucleophilic substitution reactions of phosphazenes with functional groups (alcohols, amines, thiols, etc.) have been widely studied [12][13][14][15]. Recently, derivatization of a phosphazene core with organic chromophores has attracted much attention.…”

Section: Introductionmentioning

confidence: 99%

Novel BODIPY-bridged cyclotriphosphazenes

2020

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Three new 2-component unsubstituted (4P), diiodo-(5P), and dibromo-(6P) distyryl-BODIPY-bridged cyclotriphosphazene dimers were designed and synthesized. The newly synthesized BODIPY-cyclotriphosphazene systems were characterized by 1 H, 13 C, and 31 P NMR spectroscopy. The photophysical properties of the distryl-BODIPYs (4-6) and BODIPY-cyclotriphosphazene dyads (4P-6P) were studied by UV-Vis absorption and fluorescence emission spectroscopy. In these derivatives, the bino-type cyclotriphosphazene derivative bearing unsubstituted BODIPY unit 4 P exhibited high fluorescence and no singlet oxygen generation due to the lack of spin converter. The attachment of heavy atoms (iodine and bromine) enabled the production of singlet oxygen. The bino-type BODIPY-cyclotriphosphazenes (5P and 6P) were also used as triplet photosensitizers in the photooxidation of 1,3-diphenylisobenzofuran to endoperoxide via generation of the singlet oxygen in dichloromethane. The singlet oxygen production of these compounds was also investigated via a direct method and produced a singlet oxygen phosphorescence peak at 1270 nm.

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“…Thus, new cyclotriphosphazene derivatives are synthesized. 3,4 The chemical and physical properties of these compounds can be changed depending on the type and number of the substituted side groups on the phosphorus atoms. 5−7 Therefore, cyclotriphosphazenes have found numerous applications from industrial to medical areas, such as liquid crystallines, 7 fluorescent probes, 3,5 ionic liquids, 8 flame-retardant agents, 9 and anticancer and antimicrobial agents.…”

Section: Introductionmentioning

confidence: 99%

Syntheses and characterizations of cyclotriphosphazenes containing a 4-oxy-1-naphthaldehyde group

İbişoğlu¹,

Eçik²,

Çiftçi³

2018

Turk J Chem

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The nucleophilic substitution reaction of hexachlorocyclotriphosphazene (N 3 P 3 Cl 6 , trimer) (1) with 4hydroxy-1-naphthaldehyde (2) has been investigated for the first time. 4 ′-Oxy-1 ′-naphthaldehyde substituted mono-(3), bis-(4), and tris-(5) cyclotriphosphazenes were obtained from the nucleophilic substitution of compound 1 with 2 in a 1:2 molar ratio in the presence of Cs 2 CO 3 in acetone at reflux. The pentakis-(6) and hexakis-substituted (7) cyclotriphosphazenes were prepared from the reaction of 1 with 2 in a 1:7 molar ratio using K 2 CO 3 as a proton abstractor in tetrahydrofuran at room temperature. The structures of the new compounds (3-7) were determined by elemental analysis, FT-IR, and mass and nuclear magnetic resonance (1 H and 31 P) spectroscopies.

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Synthesis and characterization of cyclotriphosphazene derivatives bearing azole groups

Cited by 15 publications

References 33 publications

NMR and DSC studies on the reactions of pentanedioxy spiro-ansa cyclochlorotriphosphazene and pentanedioxy triple-bridged cylochlorotriphosphazene with monofunctional nucleophiles

NMR and DSC studies on the reactions of pentanedioxy spiro-ansa cyclochlorotriphosphazene and pentanedioxy triple-bridged cylochlorotriphosphazene with monofunctional nucleophiles

Novel BODIPY-bridged cyclotriphosphazenes

Syntheses and characterizations of cyclotriphosphazenes containing a 4-oxy-1-naphthaldehyde group

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