KFU. Card publication. Bis(α-hydroxycycloalkyl)phosphine oxides obtained from white phosphorus via phosphine oxide H3PO: synthesis, molecular structure, coordination properties and biological activity

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BIS(α-HYDROXYCYCLOALKYL)PHOSPHINE OXIDES OBTAINED FROM WHITE PHOSPHORUS VIA PHOSPHINE OXIDE H3PO: SYNTHESIS, MOLECULAR STRUCTURE, COORDINATION PROPERTIES AND BIOLOGICAL ACTIVITY

Form of presentation

Articles in international journals and collections

Year of publication

2020

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Authors, employees of KFU

Yakhvarov Dmitriy Grigorevich, author

Bibliographic description in the original language

Bis(α-hydroxycycloalkyl)phosphine oxides obtained from white phosphorus via phosphine oxide H3PO: synthesis, molecular structure, coordination properties and biological activity / E. Gorbachuk, E. Badeeva, A. Gubaidullin, A. Samigullina, A. Voloshina, A. Sapunova, E. Hey-Hawkins, O. Sinyashin, D. Yakhvarov // ChemPlusChem – 2020. – V. 85(5). – P. 958-962.

Annotation

Reaction of the electrochemically in situ from elemental white phosphorus generated phosphine oxide H3PO in a single electrochemical cell, supplied with lead cathode and aluminium anode, with cyclic ketones (cyclopentanone and cyclohexanone) results in formation of secondary phosphine oxides (bis(α-hydroxycyclopentyl)phosphine oxide 2 a, isolated yield 15 %, and bis(α-hydroxycyclohexyl)phosphine oxide 2 b, isolated yield 12 %) with two α-hydroxycycloalkyl substituents at the phosphorus atom. Bis(α-hydroxycyclopentyl)phosphine oxide reacts with [PdCl2(COD)] (COD=1,5-cyclooctadiene) to give a new palladium complex trans-[PdCl2{P(OH)(cyclo-C5H8-1-OH)2}2] (3 a, isolated yield 11 %) bearing phosphinous acid as a ligand formed via tautomerization of the phosphine oxide. Finally, the cytotoxicity of the synthesized secondary phosphine oxides on tumor and healthy human cell lines was studied. It was found that at a concentration of 10−6–10−4 M, phosphine oxides 2 a,b exhibit similar IC50 values for the M-Hela cell line (ca. 50 mM), but are non-toxic for MCF-7 cells. For human alveolar adenocarcinoma cells (A-549), only 2 a is active (ca. 35 mM), while 2 b is not toxic.

Keywords

phosphorus chemistry, white phosphorus, secondary phosphine oxides

The name of the journal

ChemPlusChem

Please use this ID to quote from or refer to the card

https://repository.kpfu.ru/eng/?p_id=235480&p_lang=2

Full metadata record

Field DC	Value	Language
dc.contributor.author	Yakhvarov Dmitriy Grigorevich	ru_RU
dc.date.accessioned	2020-01-01T00:00:00Z	ru_RU
dc.date.available	2020-01-01T00:00:00Z	ru_RU
dc.date.issued	2020	ru_RU
dc.identifier.citation	Bis(α-hydroxycycloalkyl)phosphine oxides obtained from white phosphorus via phosphine oxide H3PO: synthesis, molecular structure, coordination properties and biological activity / E. Gorbachuk, E. Badeeva, A. Gubaidullin, A. Samigullina, A. Voloshina, A. Sapunova, E. Hey-Hawkins, O. Sinyashin, D. Yakhvarov // ChemPlusChem – 2020. – V. 85(5). – P. 958-962.	ru_RU
dc.identifier.uri	https://repository.kpfu.ru/eng/?p_id=235480&p_lang=2	ru_RU
dc.description.abstract	ChemPlusChem	ru_RU
dc.description.abstract	Reaction of the electrochemically in situ from elemental white phosphorus generated phosphine oxide H3PO in a single electrochemical cell, supplied with lead cathode and aluminium anode, with cyclic ketones (cyclopentanone and cyclohexanone) results in formation of secondary phosphine oxides (bis(α-hydroxycyclopentyl)phosphine oxide 2 a, isolated yield 15 %, and bis(α-hydroxycyclohexyl)phosphine oxide 2 b, isolated yield 12 %) with two α-hydroxycycloalkyl substituents at the phosphorus atom. Bis(α-hydroxycyclopentyl)phosphine oxide reacts with [PdCl2(COD)] (COD=1,5-cyclooctadiene) to give a new palladium complex trans-[PdCl2{P(OH)(cyclo-C5H8-1-OH)2}2] (3 a, isolated yield 11 %) bearing phosphinous acid as a ligand formed via tautomerization of the phosphine oxide. Finally, the cytotoxicity of the synthesized secondary phosphine oxides on tumor and healthy human cell lines was studied. It was found that at a concentration of 10−6–10−4 M, phosphine oxides 2 a,b exhibit similar IC50 values for the M-Hela cell line (ca. 50 mM), but are non-toxic for MCF-7 cells. For human alveolar adenocarcinoma cells (A-549), only 2 a is active (ca. 35 mM), while 2 b is not toxic.	ru_RU
dc.language.iso	ru	ru_RU
dc.subject	phosphorus chemistry	ru_RU
dc.subject	white phosphorus	ru_RU
dc.subject	secondary phosphine oxides	ru_RU
dc.title	Bis(α-hydroxycycloalkyl)phosphine oxides obtained from white phosphorus via phosphine oxide H3PO: synthesis, molecular structure, coordination properties and biological activity	ru_RU
dc.type	Articles in international journals and collections	ru_RU