[1,2]Oxazolo[5,4-e]isoindoles as promising tubulin polymerization inhibitors

Girolamo Cirrincione, Paola Barraja, Patrizia Diana, Alessandra Montalbano, Virginia Spano', Barbara Parrino, Anna Carbone, Marzia Pennati, Valentina Zuco, Nadia Zaffaroni, Alessia Lopergolo, Denis Cominetti

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Abstract

A series of [1,2]Oxazolo [5,4-e]isoindoles has been synthesized through a versatile and high yielding sequence. All the new structures showed in the 1HNMR spectra, the typical signal in the 8.34–8.47 ppm attributable to the H-3 of the [1,2]oxazole moiety. Among all derivatives, methoxy benzyl substituents at positions 3 and 4 or/and 5 were very effective in reducing the growth of different tumor cell lines, including diffuse malignant peritoneal mesothelioma (DMPM), an uncommon and rapidly malignancy poorly responsive to available therapeutic options. The most active compound 6j was found to impair tubulin polymerization, cause cell cycle arrest at G2/M phase and induce apoptosis in DMPM cells, making it as a new lead for the discovery of new potent antimitotic drugs.
Lingua originaleEnglish
pagine (da-a)840-851
Numero di pagine12
RivistaEuropean Journal of Medicinal Chemistry
Volume124
Stato di pubblicazionePublished - 2016

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Isoindoles
Tubulin Modulators
Cells
Oxazoles
Antimitotic Agents
G2 Phase
Tubulin
Cell Cycle Checkpoints
Tumor Cell Line
Polymerization
Cell Division
Tumors
Apoptosis
Derivatives
Growth
Neoplasms
Malignant Mesothelioma
Therapeutics

All Science Journal Classification (ASJC) codes

  • Pharmacology
  • Organic Chemistry
  • Drug Discovery

Cita questo

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title = "[1,2]Oxazolo[5,4-e]isoindoles as promising tubulin polymerization inhibitors",
abstract = "A series of [1,2]Oxazolo [5,4-e]isoindoles has been synthesized through a versatile and high yielding sequence. All the new structures showed in the 1HNMR spectra, the typical signal in the 8.34–8.47 ppm attributable to the H-3 of the [1,2]oxazole moiety. Among all derivatives, methoxy benzyl substituents at positions 3 and 4 or/and 5 were very effective in reducing the growth of different tumor cell lines, including diffuse malignant peritoneal mesothelioma (DMPM), an uncommon and rapidly malignancy poorly responsive to available therapeutic options. The most active compound 6j was found to impair tubulin polymerization, cause cell cycle arrest at G2/M phase and induce apoptosis in DMPM cells, making it as a new lead for the discovery of new potent antimitotic drugs.",
author = "Girolamo Cirrincione and Paola Barraja and Patrizia Diana and Alessandra Montalbano and Virginia Spano' and Barbara Parrino and Anna Carbone and Marzia Pennati and Valentina Zuco and Nadia Zaffaroni and Alessia Lopergolo and Denis Cominetti",
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language = "English",
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pages = "840--851",
journal = "European Journal of Medicinal Chemistry",
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TY - JOUR

T1 - [1,2]Oxazolo[5,4-e]isoindoles as promising tubulin polymerization inhibitors

AU - Cirrincione, Girolamo

AU - Barraja, Paola

AU - Diana, Patrizia

AU - Montalbano, Alessandra

AU - Spano', Virginia

AU - Parrino, Barbara

AU - Carbone, Anna

AU - Pennati, Marzia

AU - Zuco, Valentina

AU - Zaffaroni, Nadia

AU - Lopergolo, Alessia

AU - Cominetti, Denis

PY - 2016

Y1 - 2016

N2 - A series of [1,2]Oxazolo [5,4-e]isoindoles has been synthesized through a versatile and high yielding sequence. All the new structures showed in the 1HNMR spectra, the typical signal in the 8.34–8.47 ppm attributable to the H-3 of the [1,2]oxazole moiety. Among all derivatives, methoxy benzyl substituents at positions 3 and 4 or/and 5 were very effective in reducing the growth of different tumor cell lines, including diffuse malignant peritoneal mesothelioma (DMPM), an uncommon and rapidly malignancy poorly responsive to available therapeutic options. The most active compound 6j was found to impair tubulin polymerization, cause cell cycle arrest at G2/M phase and induce apoptosis in DMPM cells, making it as a new lead for the discovery of new potent antimitotic drugs.

AB - A series of [1,2]Oxazolo [5,4-e]isoindoles has been synthesized through a versatile and high yielding sequence. All the new structures showed in the 1HNMR spectra, the typical signal in the 8.34–8.47 ppm attributable to the H-3 of the [1,2]oxazole moiety. Among all derivatives, methoxy benzyl substituents at positions 3 and 4 or/and 5 were very effective in reducing the growth of different tumor cell lines, including diffuse malignant peritoneal mesothelioma (DMPM), an uncommon and rapidly malignancy poorly responsive to available therapeutic options. The most active compound 6j was found to impair tubulin polymerization, cause cell cycle arrest at G2/M phase and induce apoptosis in DMPM cells, making it as a new lead for the discovery of new potent antimitotic drugs.

UR - http://hdl.handle.net/10447/212856

UR - http://www.journals.elsevier.com/european-journal-of-medicinal-chemistry/

M3 - Article

VL - 124

SP - 840

EP - 851

JO - European Journal of Medicinal Chemistry

JF - European Journal of Medicinal Chemistry

SN - 0223-5234

ER -