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One-pot synthesis and biological evaluation of 2-pyrrolidinyl-4-amino-5-(3 ',4 ',5 '-trimethoxybenzoyl)thiazole: A unique, highly active antimicrotubule agent

  1. Author:
    Romagnoli, R.
    Baraldi, P. G.
    Cara, C. L.
    Salvador, M. K.
    Bortolozzi, R.
    Basso, G.
    Viola, G.
    Balzarini, J.
    Brancale, A.
    Fu, X. H.
    Li, J.
    Zhang, S. Z.
    Hamel, E.

  2. Author Address

    [Romagnoli, Romeo; Baraldi, Pier Giovanni; Cara, Carlota Lopez; Salvador, Maria Kimatrai] Univ Ferrara, Dipartimento Sci Farmaceut, I-44121 Ferrara, Italy. [Bortolozzi, Roberta; Basso, Giuseppe; Viola, Giampietro] Univ Padua, Dipartimento Pediat, Lab Oncoematol, I-35131 Padua, Italy. [Balzarini, Jan] Catholic Univ Louvain, Rega Inst Med Res, Lab Virol & Chemotherapy, B-3000 Louvain, Belgium. [Brancale, Andrea] Cardiff Univ, Welsh Sch Pharm, Cardiff CF10 3NB, S Glam, Wales. [Fu, Xian-Hua; Li, Jun; Zhang, Su-Zhan] Zhejiang Univ, Inst Canc, Key Lab Canc Prevent & Intervent, China Natl Minist Educ,Sch Med,Affiliated Hosp 2, Hangzhou 310009, Zhejiang, Peoples R China. [Hamel, Ernest] NCI, Screening Technol Branch, Dev Therapeut Program, Div Canc Treatment & Diag,NIH, Frederick, MD 21702 USA.;Romagnoli, R (reprint author), Univ Ferrara, Dipartimento Sci Farmaceut, Via Fossato Mortara 17-19, I-44121 Ferrara, Italy;rmr@unife.it giampietro.viola1@unipd.it zhangsirhao@gmail.com
    1. Year: 2011
    2. Date: Dec
  2. Journal: European Journal of Medicinal Chemistry
    1. 46
    2. 12
    3. Pages: 6015-6024
  4. Type of Article: Article
  5. ISSN: 0223-5234
  1. Abstract:

    A wide variety of small molecules with diverse molecular scaffolds inhibit microtubule formation. In this article we report a one-pot procedure for the preparation of a novel 2-(N-pyrrolidinyl)-4-amino-5-(3',4',5'-trimethoxybenzoyl)thiazole in which the size of the substituent at the C-2 position of the thiazole ring plays an essential role in compound activity. The most active agent (31) inhibited at sub-micromolar concentrations the growth of tumor cell lines. It also inhibited tubulin polymerization with an activity quantitatively similar to that of CA-4, and treatment of HeLa cells resulted in their arrest at the G2-M phase of the cell cycle. Furthermore, 3f was effective against multidrug resistant cancer cells and inhibited the growth of the HT-29 xenograft in a nude mouse model. This indicated that 31 is a promising new antimitotic agent with encouraging preclinical potential. (C) 2011 Elsevier Masson SAS. All rights reserved.

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External Sources

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  2. DOI: 10.1016/j.ejmech.2011.10.013
  3. View record in Web of Science®
  4. WOS: 000297874300032

Library Notes

  1. Fiscal Year: FY2011-2012
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