Synthesis and biological evaluation of 1-methyl-2-(3′,4′, 5′-trimethoxybenzoyl)-3-aminoindoles as a new class of antimitotic agents and tubulin inhibitors

Romeo Romagnoli, Pier Giovanni Baraldi, Taradas Sarkar, Maria Dora Carrion, Carlota Lopez Cara, Olga Cruz-Lopez, Delia Preti, Mojgan Aghazadeh Tabrizi, Manlio Tolomeo, Stefania Grimaudo, Antonella Di Cristina, Nicola Zonta, Jan Balzarini, Andrea Brancale, Hsing Pang Hsieh, Ernest Hamel

Research output: Contribution to journalArticlepeer-review

82 Citations (Scopus)

Abstract

The 2-(3,4,5-trimethoxybenzoyl)-2-aminoindole nucleus was used as the fundamental structure for the synthesis of compounds modified with respect to positions C-4 to C-7 with different moieties (chloro, methyl, or methoxy). Additional structural variations concerned the indole nitrogen, which was alkylated with small alkyl groups such as methyl or ethyl. We have identified 1-methyl-2-(3,4,5-trimethoxybenzoyl)-3-amino-7-methoxyindole as a new highly potent antiproliferative agent that targets tubulin at the colchicine binding site and leads to apoptotic cell death.

Original languageEnglish
Pages (from-to)1464-1468
Number of pages5
JournalJournal of Medicinal Chemistry
Volume51
Issue number5
DOIs
Publication statusPublished - 2008 Mar 13

All Science Journal Classification (ASJC) codes

  • Molecular Medicine
  • Drug Discovery

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