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Design and synthesis of spirotryprostatin-inspired diketopiperazine systems from prolyl spirooxoindolethiazolidine derivatives.

Abstract：

:Based on the spirotryprostatin-A structure, we designed, synthesized, and evaluated different series of compounds belonging to the diketopiperazine structural class as potential cell cycle modulators and cytotoxic agents. Starting from the spirooxoindolthiazolidine scaffold, amide coupling with Pro derivatives and intramolecular cyclization reactions are suitable synthetic methods to generate chemically diverse diketopiperazine system, such as hexahydropyrrolo[1,2-a][1,3]thiazolo[3,2-d]pyrazine-5,10-dione (structure I), hexahydropyrrolo[1,2-a] [1,3]thiazolo[3,4-d]pyrazine-5,10-dione (structure II) and spiroindol-2-one[3,3']hexahydro-5,10H-pyrrolo[1,2-a][1,3]thiazolo[3,4-d]pyrazine-5,10-dione (structure III). Some of these compounds, especially those who belong to the series I and II, showed interesting cytotoxic activity.

journal_name

Bioorg Med Chem

journal_title

Bioorganic & medicinal chemistry

authors

Bertamino A,Aquino C,Sala M,Simone Nd,Mattia CA,Erra L,Musella S,Iannelli P,Carotenuto A,Grieco P,Novellino E,Campiglia P,Gomez-Monterrey I

doi

10.1016/j.bmc.2010.04.079

subject

Has Abstract

pub_date

2010-06-15 00:00:00

pages

4328-37

issue

12

eissn

0968-0896

issn

1464-3391

pii

S0968-0896(10)00391-3

journal_volume

18

pub_type

杂志文章

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