Literature DB >> 18755591

Synthesis and biological evaluation of 2-(3',4',5'-trimethoxybenzoyl)-3-N,N-dimethylamino benzo[b]furan derivatives as inhibitors of tubulin polymerization.

Romeo Romagnoli1, Pier Giovanni Baraldi, Taradas Sarkar, Maria Dora Carrion, Olga Cruz-Lopez, Carlota Lopez Cara, Manlio Tolomeo, Stefania Grimaudo, Antonietta Di Cristina, Maria Rosaria Pipitone, Jan Balzarini, Roberto Gambari, Lampronti Ilaria, Roberto Saletti, Andrea Brancale, Ernest Hamel.   

Abstract

Molecules that target microtubules have an important role in the treatment of cancer. A new class of inhibitors of tubulin polymerization based on the 2-(3,4,5-trimethoxybenzoyl)-2-dimethylamino-benzo[b]furan molecular skeleton was synthesized and evaluated for antiproliferative activity, inhibition of tubulin polymerization, and cell cycle effects. The most promising compound in this series was 2-(3,4,5-trimethoxybenzoyl)-3-dimethylamino-6-methoxy-benzo[b]furan, which inhibits cancer cell growth at nanomolar concentrations and interacts strongly with tubulin by binding to the colchicine site.

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Year:  2008        PMID： 18755591      PMCID： PMC2574800          DOI： 10.1016/j.bmc.2008.08.029

Source DB:  PubMed          Journal:  Bioorg Med Chem        ISSN： 0968-0896            Impact factor:   3.641


  19 in total

1.  One-pot synthesis of benzo[b]furan and indole inhibitors of tubulin polymerization.

Authors:  Bernard L Flynn; Ernest Hamel; M Katherine Jung
Journal:  J Med Chem       Date:  2002-06-06       Impact factor: 7.446

2.  Insight into tubulin regulation from a complex with colchicine and a stathmin-like domain.

Authors:  Raimond B G Ravelli; Benoît Gigant; Patrick A Curmi; Isabelle Jourdain; Sylvie Lachkar; André Sobel; Marcel Knossow
Journal:  Nature       Date:  2004-03-11       Impact factor: 49.962

3.  Antimitotic natural products combretastatin A-4 and combretastatin A-2: studies on the mechanism of their inhibition of the binding of colchicine to tubulin.

Authors:  C M Lin; H H Ho; G R Pettit; E Hamel
Journal:  Biochemistry       Date:  1989-08-22       Impact factor: 3.162

4.  Isolation and structure of the strong cell growth and tubulin inhibitor combretastatin A-4.

Authors:  G R Pettit; S B Singh; E Hamel; C M Lin; D S Alberts; D Garcia-Kendall
Journal:  Experientia       Date:  1989-02-15

5.  Structure-activity analysis of the interaction of curacin A, the potent colchicine site antimitotic agent, with tubulin and effects of analogs on the growth of MCF-7 breast cancer cells.

Authors:  P Verdier-Pinard; J Y Lai; H D Yoo; J Yu; B Marquez; D G Nagle; M Nambu; J D White; J R Falck; W H Gerwick; B W Day; E Hamel
Journal:  Mol Pharmacol       Date:  1998-01       Impact factor: 4.436

6.  Benzoylurea derivatives as a novel class of antimitotic agents: synthesis, anticancer activity, and structure-activity relationships.

Authors:  Dan-Qing Song; Yan Wang; Lian-Zong Wu; Peng Yang; Yue-Ming Wang; Li-Mei Gao; Yan Li; Jing-Rong Qu; Yong-Hong Wang; Ying-Hong Li; Na-Na Du; Yan-Xing Han; Zhi-Ping Zhang; Jian-Dong Jiang
Journal:  J Med Chem       Date:  2008-05-06       Impact factor: 7.446

7.  The disruption of brain microtubules in vitro by the phospholipase inhibitor p-bromophenacyl bromide.

Authors:  A J Hargreaves; A P Glazier; J Flaskos; F H Mullins; W G McLean
Journal:  Biochem Pharmacol       Date:  1994-03-29       Impact factor: 5.858

8.  Synthesis, cancericidal and antimicrotubule activities of 3-(haloacetamido)-benzoylureas.

Authors:  J D Jiang; J Roboz; I Weisz; L Deng; L Ma; J F Holland; J G Bekesi
Journal:  Anticancer Drug Des       Date:  1998-10

9.  Separation of active tubulin and microtubule-associated proteins by ultracentrifugation and isolation of a component causing the formation of microtubule bundles.

Authors:  E Hamel; C M Lin
Journal:  Biochemistry       Date:  1984-08-28       Impact factor: 3.162

Review 10.  Tubulin sulfhydryl groups as probes and targets for antimitotic and antimicrotubule agents.

Authors:  R F Luduena; M C Roach
Journal:  Pharmacol Ther       Date:  1991       Impact factor: 12.310
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  6 in total

1.  Novel iodoacetamido benzoheterocyclic derivatives with potent antileukemic activity are inhibitors of STAT5 phosphorylation.

Authors:  Romeo Romagnoli; Pier Giovanni Baraldi; Filippo Prencipe; Carlota Lopez-Cara; Riccardo Rondanin; Daniele Simoni; Ernest Hamel; Stefania Grimaudo; Rosaria Maria Pipitone; Maria Meli; Manlio Tolomeo
Journal:  Eur J Med Chem       Date:  2015-11-27       Impact factor: 6.514

2.  Synthesis and antitumor molecular mechanism of agents based on amino 2-(3',4',5'-trimethoxybenzoyl)benzo[b]furan: inhibition of tubulin and induction of apoptosis.

Authors:  Romeo Romagnoli; Pier Giovanni Baraldi; Carlota Lopez-Cara; Olga Cruz-Lopez; Maria Dora Carrion; Maria Kimatrai Salvador; Jaime Bermejo; Sara Estévez; Francisco Estévez; Jan Balzarini; Andrea Brancale; Antonio Ricci; Longchuan Chen; Jae Gwan Kim; Ernest Hamel
Journal:  ChemMedChem       Date:  2011-08-01       Impact factor: 3.466

3.  Molecular modeling study, synthesis and biological evaluation of combretastatin A-4 analogues as anticancer agents and tubulin inhibitors.

Authors:  Yang Ping Quan; Li Ping Cheng; Tian Chi Wang; Wan Pang; Fan Hong Wu; Jin Wen Huang
Journal:  Medchemcomm       Date:  2017-12-06       Impact factor: 3.597

4.  Synthesis and Evaluation of Haloacetyl, α-Bromoacryloyl and Nitrooxyacetyl Benzo[b]furan and Benzo[b]thiophene Derivatives as Potent Antiproliferative Agents Against Leukemia L1210 and K562 Cells.

Authors:  Romeo Romagnoli; Pier Giovanni Baraldi; Maria Dora Carrion; Carlota Lopez Cara; Alberto Casolari; Ernest Hamel; Enrica Fabbri; Roberto Gambari
Journal:  Lett Drug Des Discov       Date:  2010-08-01       Impact factor: 1.150

5.  Design, synthesis, in vitro, and in vivo anticancer and antiangiogenic activity of novel 3-arylaminobenzofuran derivatives targeting the colchicine site on tubulin.

Authors:  Romeo Romagnoli; Pier Giovanni Baraldi; Maria Kimatrai Salvador; Filippo Prencipe; Carlota Lopez-Cara; Santiago Schiaffino Ortega; Andrea Brancale; Ernest Hamel; Ignazio Castagliuolo; Stefania Mitola; Roberto Ronca; Roberta Bortolozzi; Elena Porcù; Giuseppe Basso; Giampietro Viola
Journal:  J Med Chem       Date:  2015-03-26       Impact factor: 7.446

6.  Design, synthesis and structure-activity relationship of 2-(3',4',5'-trimethoxybenzoyl)-benzo[b]furan derivatives as a novel class of inhibitors of tubulin polymerization.

Authors:  Romeo Romagnoli; Pier Giovanni Baraldi; Maria Dora Carrion; Carlota Lopez Cara; Olga Cruz-Lopez; Manlio Tolomeo; Stefania Grimaudo; Antonietta Di Cristina; Maria Rosaria Pipitone; Jan Balzarini; Nicola Zonta; Andrea Brancale; Ernest Hamel
Journal:  Bioorg Med Chem       Date:  2009-08-20       Impact factor: 3.641
  6 in total

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