- Click-based synthesis of bromotyrosine alkaloid analogs as potential anti-biofilm leads for SAR studies
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A library of triazole-based analogs of bromotyramine alkaloids such as verongamines, hemibastadins, pseudoceramine D and clavatidine E was designed in order to identify promising leads that may help in the control of bacterial biofilms. Twenty-three compounds were screened for their biofilm inhibitory activity against three strains of Gram-negative bacteria. SAR studies revealed that hemibastadins analogs were the most active compounds which act as inhibitors of biofilm development (EC50 8.8-29 μM) without effect on bacterial growth even at high concentrations (100 μM).
- Andjouh,Blache
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- RAFT polymerization of bromotyramine-based 4-acryloyl-1,2,3-triazole: A functional monomer and polymer family through click chemistry
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Four new functional acryloyl-triazole monomers derived from bromotyramine were successfully synthesized. These monomers were prepared in an efficient way from organic azides and propargyl acrylate via a copper catalyzed 1,3-dipolar cycloaddition. Polymers containing bromotyramine as a pendant group were obtained via reversible addition-fragmentation chain transfer (RAFT) polymerization. The influence of the chain transfer agent (CTA), solvent, temperature and the length of the linker between the triazole and bromotyramine groups on the polymerization kinetics was studied. It was found that triazoles containing acrylate monomers are characterized by fast polymerization and polymers with controlled molar masses (20 000 g mol-1) and low dispersities (DM 1.5) can be prepared. Glass transition temperatures of these acrylic polymers ranged from 48 °C to 20 °C by controlling the length of the linker between the bromotyramine side groups and the backbone.
- Andjouh, Sofyane,Bressy, Christine,Blache, Yves
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p. 14496 - 14504
(2016/02/19)
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- 1,2,3-Triazole analogs of combretastatin A-4 as potential microtubule-binding agents
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A series of cis-restricted 1,4- and 1,5-disubstituted 1,2,3-triazole analogs of combretastatin A-4 (1) have been prepared. Cytotoxicity and tubulin inhibition studies showed that 2-methoxy-5-((5-(3,4,5-trimethoxyphenyl)-1H-1,2, 3-triazol-1-yl)methyl)aniline (5e) and 2-methoxy-5-(1-(3,4,5-trimethoxybenzyl)- 1H-1,2,3-triazol-5-yl)aniline (6e) were two of the most active compounds. Molecular modeling studies revealed that the N-2 and N-3 atoms in the triazole rings in 5e and 6e did not form hydrogen bonds with the amino acids in the anticipated pharmacophore.
- Odlo, Kristin,Fournier-Dit-Chabert, Jérémie,Ducki, Sylvie,Gani, Osman A.B.S.M.,Sylte, Ingebrigt,Hansen, Trond Vidar
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experimental part
p. 6874 - 6885
(2010/10/19)
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