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. Copyright 2010 Elsevier Ltd. All rights reserved

Design and Synthesis of Spirotryprostatin-inspired Diketopiperazine Systemsfrom Prolyl Spirooxoindolethiazolidine Derivatives / Bertamino, Alessia; Aquino, Claudio; M., Sala; N., de Simone; C. A., Mattia; L., Erra; S., Musella; P., Iannelli; Carotenuto, Alfonso; Grieco, Paolo; Novellino, Ettore; P., Campiglia; GOMEZ MONTERREY, ISABEL MARIA. - In: BIOORGANIC & MEDICINAL CHEMISTRY. - ISSN 1464-3391. - STAMPA. - 18:12(2010), pp. 4328-4337. [10.1016/j.bmc.2010.04.079]

Design and Synthesis of Spirotryprostatin-inspired Diketopiperazine Systemsfrom Prolyl Spirooxoindolethiazolidine Derivatives

BERTAMINO, ALESSIA;AQUINO, CLAUDIO;CAROTENUTO, ALFONSO;GRIECO, PAOLO;NOVELLINO, ETTORE;GOMEZ MONTERREY, ISABEL MARIA
2010

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. Copyright 2010 Elsevier Ltd. All rights reserved
2010
Design and Synthesis of Spirotryprostatin-inspired Diketopiperazine Systemsfrom Prolyl Spirooxoindolethiazolidine Derivatives / Bertamino, Alessia; Aquino, Claudio; M., Sala; N., de Simone; C. A., Mattia; L., Erra; S., Musella; P., Iannelli; Carotenuto, Alfonso; Grieco, Paolo; Novellino, Ettore; P., Campiglia; GOMEZ MONTERREY, ISABEL MARIA. - In: BIOORGANIC & MEDICINAL CHEMISTRY. - ISSN 1464-3391. - STAMPA. - 18:12(2010), pp. 4328-4337. [10.1016/j.bmc.2010.04.079]
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11588/374780
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