Synthesis, isomerization and biological activity of novel 2-selenohydantoin derivatives.
Bioorg Med Chem
; 24(4): 802-11, 2016 Feb 15.
Article
in En
| MEDLINE
| ID: mdl-26780833
ABSTRACT
A set of novel selenohydantoins were synthesized via a convenient and versatile approach involving the reaction of isoselenocyanates with various amines. We also revealed an unexpected ZâE isomerization of pyridin-2-yl-substituted selenohydantoins in the presence of Cu(2+) cations. The detailed mechanism of this transformation was suggested on the basis of quantum-chemical calculations, and the key role of Cu(2+) was elucidated. The obtained compounds were subsequently evaluated against a panel of different cancer cell lines. As a result, several molecules were identified as promising micromolar hits with good selectivity index. Instead of analogous thiohydantoins, which have been synthesized previously, selenohydantoins demonstrated a relatively high antioxidant activity comparable (or greater) to the reference molecule, Ebselen, a clinically approved drug candidate. The most active compounds have been selected for further biological trials.
Key words
Full text:
1
Collection:
01-internacional
Database:
MEDLINE
Main subject:
Organoselenium Compounds
/
Hydantoins
/
Antineoplastic Agents
/
Antioxidants
Limits:
Humans
Language:
En
Journal:
Bioorg Med Chem
Journal subject:
BIOQUIMICA
/
QUIMICA
Year:
2016
Document type:
Article