Nucleophilic substitutions in the isoindole series as a valuable tool to synthesize derivatives with antitumor activity
作者： Patrizia Diana , Annamaria Martorana , Paola Barraja , Alessandra Montalbano , Anna Carbone
DOI: 10.1016/J.TET.2011.01.056
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摘要: Abstract A novel synthetic approach to the synthesis of 3-substituted isoindoles through nucleophilic substitution 3-halo derivatives by charged carbon, and neutral nitrogen, oxygen, sulfur nucleophiles, assisted a 1-acyl group, is reported. Aryl-thio-isoindoles, obtained direct with showed cytotoxic activity, GI50 values from micromolar sub-micromolar concentrations, against total number cell lines investigated.
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F S Babichev, V A Kovtunenko, A K Tyltin, Advances in the Chemistry of Isoindole Russian Chemical Reviews. ,vol. 50, pp. 1087- 1103 ,(1981) , 10.1070/RC1981V050N11ABEH002738
Mary Ann Jordan, Leslie Wilson, Microtubules as a target for anticancer drugs. Nature Reviews Cancer. ,vol. 4, pp. 253- 265 ,(2004) , 10.1038/NRC1317
George R. Pettit, Sheo Bux Singh, Michael R. Boyd, Ernest Hamel, Robin K. Pettit, Jean M. Schmidt, Fiona Hogan, Antineoplastic Agents. 291. Isolation and Synthesis of Combretastatins A-4, A-5, and A-6 Journal of Medicinal Chemistry. ,vol. 38, pp. 1666- 1672 ,(1995) , 10.1021/JM00010A011
Olga V. Hordiyenko, Igor V. Rudenko, Angelina V. Biitseva, Aleksandr V. Turov, Axelle Arrault, Nicolas Brosse, Olivier Fabre, Brigitte Jamart-Grégoire, Roman I. Zubatyuk, Oleg V. Shishkin, Efficient preparation of N′,N″-1H-isoindole-1,3-diylidenedicarbohydrazides via 1,1,3-trichloro-1H-isoindole, and their characterization Tetrahedron. ,vol. 65, pp. 6218- 6225 ,(2009) , 10.1016/J.TET.2009.05.031
Patrizia Diana, Annamaria Martorana, Paola Barraja, Alessandra Montalbano, Gaetano Dattolo, Girolamo Cirrincione, Francesco Dall’Acqua, Alessia Salvador, Daniela Vedaldi, Giuseppe Basso, Giampietro Viola, Isoindolo[2,1-a]quinoxaline derivatives, novel potent antitumor agents with dual inhibition of tubulin polymerization and topoisomerase I. Journal of Medicinal Chemistry. ,vol. 51, pp. 2387- 2399 ,(2008) , 10.1021/JM070834T
Paola Barraja, Patrizia Diana, Anna Carbone, Girolamo Cirrincione, None, Nucleophilic reactions in the indole series: displacement of bromine under phase transfer catalysis Tetrahedron. ,vol. 64, pp. 11625- 11631 ,(2008) , 10.1016/J.TET.2008.10.022
Raimond B.G. Ravelli, Benoît Gigant, Patrick A. Curmi, Isabelle Jourdain, Sylvie Lachkar, André Sobel, Marcel Knossow, Insight into tubulin regulation from a complex with colchicine and a stathmin-like domain Nature. ,vol. 428, pp. 198- 202 ,(2004) , 10.1038/NATURE02393
Paola Barraja, Virginia Spanò, Diana Patrizia, Anna Carbone, Girolamo Cirrincione, Daniela Vedaldi, Alessia Salvador, Giampietro Viola, Francesco Dall’Acqua, None, Pyrano[2,3-e]isoindol-2-ones, new angelicin heteroanalogues Bioorganic & Medicinal Chemistry Letters. ,vol. 19, pp. 1711- 1714 ,(2009) , 10.1016/J.BMCL.2009.01.096
Giuseppe La Regina, Michael C. Edler, Andrea Brancale, Sahar Kandil, Antonio Coluccia, Francesco Piscitelli, Ernest Hamel, Gabriella De Martino, Ruth Matesanz, José Fernando Díaz, Anna Ivana Scovassi, Ennio Prosperi, Antonio Lavecchia, Ettore Novellino, Marino Artico, Romano Silvestri, Arylthioindole inhibitors of tubulin polymerization. 3. Biological evaluation, structure-activity relationships and molecular modeling studies Journal of Medicinal Chemistry. ,vol. 50, pp. 2865- 2874 ,(2007) , 10.1021/JM061479U
Eddy Pasquier, Nicolas Andre, Diane Braguer, Targeting microtubules to inhibit angiogenesis and disrupt tumour vasculature: implications for cancer treatment. Current Cancer Drug Targets. ,vol. 7, pp. 566- 581 ,(2007) , 10.2174/156800907781662266