Synthesis and Biological Evaluations of Click-Generated Nitrogen Mustards |
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Authors: | Benjamin Boëns Tan-Sothea Ouk Yves Champavier Rachida Zerrouki |
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Institution: | 1. Laboratoire de Chimie des Substances Naturelles, Albert Thomas, Limoges, France;2. Faculté de Médecine et de Pharmacie, Marcland, Limoges, France |
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Abstract: | This paper describes the synthesis of new click-generated nitrogen mustards and their biological evaluation. By using the copper-catalyzed azide-alkyne cycloaddition (CuAAC) reaction, we managed to synthesize eight new nitrogen mustards. This strategy paves the way for the synthesis of a new family of nitrogen mustard, with an important structural variability. Furthermore, we studied the biological activity of synthesized compounds by testing their cytotoxicity on four representative cancer cell lines A431, JURKAT, K562, and U266. One structure, 1-benzyl-4-(N,N-di-2-chloroethylaminomethyl)-1H-1 Noll, D.M.; McG.Mason, T.; Miller, P.S. Formation and repair of interstrand cross-links in DNA. Chem. Rev. 2006, 106, 277–301.Crossref], PubMed], Web of Science ®] , Google Scholar],2 Rink, S.M.; Hopkins, P.B. Direct evidence for DNA intrastrand cross-linking by the nitrogen mustard mechlorethamine in synthetic oligonucleotides. Bioorg. Med. Chem. Lett. 1995, 5(23), 2845–2850.Crossref], Web of Science ®] , Google Scholar],3 Chabner, B.A.; Collins, J.M. Cancer Chemotherapy: Principles and Practices, PA, J.B. Lippincott Company, Philadelphia, 1990, pp. 276–313. Google Scholar]]triazole, showed an interesting cytotoxic effect. |
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Keywords: | Nitrogen mustards click chemistry CuAAC reaction MTT assays |
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