Synthesis and biological evaluation of 2-(3',4',5'-trimethoxybenzoyl)-3-amino 5-aryl thiophenes as a new class of tubulin inhibitors.

Stefania Grimaudo, Francesca Fruttarolo, Vincent Remusat, Delia Preti, Maria Giovanna Pavani, Maria Dora Carrion, Pier Giovanni Baraldi, Romeo Romagnoli, Carlota Lopez Cara, Ernest Hamel, Mojgan Aghazadeh Tabrizi, Jan Balzarini, Mary Ann Jordan

Research output: Contribution to journalArticle

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Abstract

2-(3‘,4‘,5‘-Trimethoxybenzoyl)-3-amino-5-aryl/heteroaryl thiophene derivatives were synthesized and evaluated for antiproliferative activity, inhibition of tubulin polymerization, and cell cycle effects. SARs were elucidated with various substitutions on the aryl moiety 5-position of the thienyl ring. Substituents at the para-position of the 5-phenyl group showed antiproliferative activity in the order of FCH3 > OCH3BrNO2 > CF3I > OEt. Several of these compounds led to arrest of HL-60 cells in the G2/M phase of the cell cycle and induction of apoptosis.
Original languageEnglish
Pages (from-to)6425-6428
Number of pages4
JournalJournal of Medicinal Chemistry
Volume49
Publication statusPublished - 2006

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Tubulin Modulators
Thiophenes
Cell Cycle
G2 Phase
HL-60 Cells
Tubulin
Polymerization
Cell Division
Apoptosis

All Science Journal Classification (ASJC) codes

  • Molecular Medicine
  • Drug Discovery

Cite this

Grimaudo, S., Fruttarolo, F., Remusat, V., Preti, D., Pavani, M. G., Carrion, M. D., ... Jordan, M. A. (2006). Synthesis and biological evaluation of 2-(3',4',5'-trimethoxybenzoyl)-3-amino 5-aryl thiophenes as a new class of tubulin inhibitors. Journal of Medicinal Chemistry, 49, 6425-6428.

Synthesis and biological evaluation of 2-(3',4',5'-trimethoxybenzoyl)-3-amino 5-aryl thiophenes as a new class of tubulin inhibitors. / Grimaudo, Stefania; Fruttarolo, Francesca; Remusat, Vincent; Preti, Delia; Pavani, Maria Giovanna; Carrion, Maria Dora; Baraldi, Pier Giovanni; Romagnoli, Romeo; Lopez Cara, Carlota; Hamel, Ernest; Aghazadeh Tabrizi, Mojgan; Balzarini, Jan; Jordan, Mary Ann.

In: Journal of Medicinal Chemistry, Vol. 49, 2006, p. 6425-6428.

Research output: Contribution to journalArticle

Grimaudo, S, Fruttarolo, F, Remusat, V, Preti, D, Pavani, MG, Carrion, MD, Baraldi, PG, Romagnoli, R, Lopez Cara, C, Hamel, E, Aghazadeh Tabrizi, M, Balzarini, J & Jordan, MA 2006, 'Synthesis and biological evaluation of 2-(3',4',5'-trimethoxybenzoyl)-3-amino 5-aryl thiophenes as a new class of tubulin inhibitors.', Journal of Medicinal Chemistry, vol. 49, pp. 6425-6428.
Grimaudo, Stefania ; Fruttarolo, Francesca ; Remusat, Vincent ; Preti, Delia ; Pavani, Maria Giovanna ; Carrion, Maria Dora ; Baraldi, Pier Giovanni ; Romagnoli, Romeo ; Lopez Cara, Carlota ; Hamel, Ernest ; Aghazadeh Tabrizi, Mojgan ; Balzarini, Jan ; Jordan, Mary Ann. / Synthesis and biological evaluation of 2-(3',4',5'-trimethoxybenzoyl)-3-amino 5-aryl thiophenes as a new class of tubulin inhibitors. In: Journal of Medicinal Chemistry. 2006 ; Vol. 49. pp. 6425-6428.
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AU - Remusat, Vincent

AU - Preti, Delia

AU - Pavani, Maria Giovanna

AU - Carrion, Maria Dora

AU - Baraldi, Pier Giovanni

AU - Romagnoli, Romeo

AU - Lopez Cara, Carlota

AU - Hamel, Ernest

AU - Aghazadeh Tabrizi, Mojgan

AU - Balzarini, Jan

AU - Jordan, Mary Ann

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AB - 2-(3‘,4‘,5‘-Trimethoxybenzoyl)-3-amino-5-aryl/heteroaryl thiophene derivatives were synthesized and evaluated for antiproliferative activity, inhibition of tubulin polymerization, and cell cycle effects. SARs were elucidated with various substitutions on the aryl moiety 5-position of the thienyl ring. Substituents at the para-position of the 5-phenyl group showed antiproliferative activity in the order of FCH3 > OCH3BrNO2 > CF3I > OEt. Several of these compounds led to arrest of HL-60 cells in the G2/M phase of the cell cycle and induction of apoptosis.

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