Repozytorium

New chiral Mannich adducts of di-tert-butylphenols and a bicyclic imine : synthesis and antiproliferative activity.

Autorzy

Jakub Iwanejko

Elżbieta Wojaczyńska

Justyna Trynda

Magdalena Maciejewska

Joanna Wietrzyk

Andrzej Kochel

Jacek Wojaczyński

Rok wydania

2017

Czasopismo

Tetrahedron

Numer woluminu

73

Strony

2276-2282

DOI

10.1016/j.tet.2017.03.017

Kolekcja

Naukowa

Język

Angielski

Typ publikacji

Artykuł

Streszczenie

Tests of antiproliferative activity of Mannich adducts of aromatic nucleophiles and a chiral bicyclic imine revealed a di-tert-butylphenol derivative as a promising compound for further exploration. To study the influence of substitution pattern and a configuration of stereogenic centers on the inhibition of cancer cell growth, a series of Mannich bases were obtained with a good to high diastereoselectivity from the reaction of the imine and three isomeric di-tert-butylphenols. Six new enantiopure adducts were isolated and fully characterized. Selected derivatives were shown to exhibit an interesting antiproliferative activity comparable to cisplatin.

Słowa kluczowe

antiproliferative activity, imines, Mannich bases, Mannich reaction, Stereoselectivity

Adres publiczny

http://dx.doi.org/10.1016/j.tet.2017.03.017

Strona internetowa wydawcy

http://www.elsevier.com

Podobne publikacje
2014

Stereoselective preparation of chiral compounds in Mannich-type reactions of a bicyclic imine and phenols or indole.

Iwanejko Jakub, Wojaczyńska Elżbieta, Wojaczyński Jacek, Bąkowicz Julia

2021

Cytotoxic activity of piperazin-2-one-based structures: cyclic imines, lactams, aminophosphonates, and their derivatives.

Iwanejko Jakub, Samadaei Mahzeiar, Pinter Matthias, Senfter Daniel, Madlener Sibylle, Kochel Andrzej, Rohr-Udilova Nataliya, Wojaczyńska Elżbieta

2010

Competitive intra- and intermolecular interactions in secondary Mannich bases.

Kołodziejczak Jerzy, Adamczyk-Wożniak A., Sporzyński A., Kochel Andrzej, Koll Aleksander