Premium
Bis(α‐hydroxycycloalkyl)phosphine Oxides Obtained from White Phosphorus via Phosphine Oxide H 3 PO: Synthesis, Molecular Structure, Coordination Properties and Biological Activity
Author(s) -
Gorbachuk Elena,
Badeeva Elena,
Gubaidullin Aidar,
Samigullina Aida,
Voloshina Alexandra,
Sapunova Anastasiia,
HeyHawkins Evamarie,
Sinyashin Oleg,
Yakhvarov Dmitry
Publication year - 2020
Publication title -
chempluschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.801
H-Index - 61
ISSN - 2192-6506
DOI - 10.1002/cplu.202000220
Subject(s) - chemistry , phosphine , phosphine oxide , white phosphorus , oxide , inorganic chemistry , yield (engineering) , medicinal chemistry , nuclear chemistry , phosphorus , organic chemistry , catalysis , materials science , metallurgy
Reaction of the electrochemically in situ from elemental white phosphorus generated phosphine oxide H 3 PO 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 [PdCl 2 (COD)] (COD=1,5‐cyclooctadiene) to give a new palladium complex trans ‐[PdCl 2 {P(OH)( cyclo ‐C 5 H 8 ‐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 IC 50 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.