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Synthesis of New Diketopiperazines, Thiolation to Thiodiketopiperazines, and Examination of Their ROS‐Generating Properties
Author(s) -
Zhong Sabilla,
Wandler Angela E. E.,
Schepers Ute,
Nieger Martin,
Bräse Stefan
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201500900
Subject(s) - diketopiperazines , chemistry , pyroglutamic acid , amino acid , combinatorial chemistry , block (permutation group theory) , hela , stereochemistry , biochemistry , geometry , mathematics , cell
Abstract A variety of new symmetrical and unsymmetrical diketopiperazines have been prepared from free amino acids by using a previously developed microwave‐assisted protocol. This included the successful incorporation of L ‐pyroglutamic acid as an unusual building block. The diketopiperazines were then thiolated electrophilically to the corresponding bis(methylthio)‐ and epidithiodiketopiperazines. Initial experiments showed a promising activity towards the generation of reactive oxygen species in HeLa cells.