Synthesis and medicinal chemical characterisation of antiproliferative O,N-functionalised isopulegol derivatives.
RSC Adv
; 14(26): 18508-18518, 2024 Jun 06.
Article
em En
| MEDLINE
| ID: mdl-38867736
ABSTRACT
Benzylation of isopulegol furnished O-benzyl-protected isopulegol, which was transformed into aminodiols via epoxidation followed by ring opening of the corresponding epoxides and subsequent hydrogenolysis. On the other hand, (-)-isopulegol was oxidised to a diol, which was then converted into dibenzyl-protected diol derivatives. The products were then transformed into aminotriols by using a similar method. The antiproliferative activity of aminodiol and aminotriol derivatives was examined. In addition, structure-activity relationships were also explored from the aspects of substituent effects and stereochemistry on the aminodiol and aminotriol systems. The drug-likeness of the compounds was assessed by in silico and experimental physicochemical characterisations, completed by kinetic aqueous solubility and in vitro intestinal-specific parallel artificial membrane permeability assay (PAMPA-GI) measurements.
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Coleções:
01-internacional
Base de dados:
MEDLINE
Idioma:
En
Revista:
RSC Adv
Ano de publicação:
2024
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Article