Synthesis of New Diketopiperazines, Thiolation to Thiodiketopiperazines, and Examination of Their ROS‐Generating Properties | Zendy

Zhong Sabilla | Zendy; Wandler Angela E. E. | Zendy; Schepers Ute | Zendy; Nieger Martin | Zendy; Bräse Stefan | Zendy

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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

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.

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