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 reservedI documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
