- Cyclic Diaryl λ3-Bromanes: A Rapid Access to Molecular Complexity via Cycloaddition Reactions
-
Biaryls have widespread applications in organic synthesis. However, sequentially polysubstituted biaryls are underdeveloped due to their challenging preparation. Herein, we report the synthesis of dissymetric 2,3,2′,3′,4-substituted biaryls via pericyclic reactions of cyclic diaryl λ3-bromanes. The functional groups tolerance and atom economy allow access to molecular complexity in a single reaction step. Continuous flow protocol has been designed for the scale-up of the reaction, while postfunctionalizations have been developed taking advantage of the residual Br-atom.
- Lanzi, Matteo,Ali Abdine, Racha Abed,De Abreu, Maxime,Wencel-Delord, Joanna
-
p. 9047 - 9052
(2021/12/06)
-
- Synthesis and Biological Evaluation of Hapten-Clicked Analogues of The Antigenic Peptide Melan-A/MART-126(27L)-35
-
A click-chemistry-based approach was implemented to prepare peptidomimetics designed in silico and made from aromatic azides and a propargylated GIGI-mimicking platform derived from the altered Melan-A/MART-126(27L)-35 antigenic peptide ELAGIGILTV. The CuI-catalyzed Huisgen cycloaddition was carried out on solid support to generate rapidly a first series of peptidomimetics, which were evaluated for their capacity to dock at the interface between the major histocompatibility complex class-I (MHC-I) human leucocyte antigen (HLA)-A2 and T-cell receptors (TCRs). Despite being a weak HLA-A2 ligand, one of these 11 first synthetic compounds bearing a p-nitrobenzyl-triazole side chain was recognized by the receptor proteins of Melan-A/MART-1-specific T-cells. After modification of the N and C termini of this agonist, which was intended to enhance HLA-A2 binding, one of the resulting seven additional compounds triggered significant T-cell responses. Thus, these results highlight the capacity of naturally circulating human TCRs that are specific for the native Melan-A/MART-126-35 peptide to cross-react with peptidomimetics bearing organic motifs structurally different from the native central amino acids.
- Tarbe, Marion,Miles, John J.,Edwards, Emily S. J.,Miles, Kim M.,Sewell, Andrew K.,Baker, Brian M.,Quideau, Stéphane
-
p. 799 - 807
(2020/04/20)
-
- Redox reaction between benzyl azides and aryl azides: concerted synthesis of aryl nitriles and anilines
-
A unique and novel reaction between benzyl azides and aryl azides is described to synthesize aryl nitriles and anilines concurrently, which is catalyzed with a photoactivated diruthenium complex. N-Unsubstituted imines (N-H imines) are generated first from benzyl azides, followed by the hydrogen transfer reaction between N-H imines and aryl azides. A wide range of aryl nitriles and anilines were synthesized under neutral and mild reaction conditions.
- Kim, Yongjin,Rhee, Young Ho,Park, Jaiwook
-
p. 1636 - 1641
(2017/02/23)
-
- Synthesis, electrochemistry and anticancer activity of novel ferrocenyl phenols prepared via azide-alkyne 1,3-cycloaddition reaction
-
A series of monophenols and diphenols containing the ferrocene-C triazolyl and ferrocene-Ntriazolyl bond were prepared in a cycloaddition reaction of ethynylferrocene with aryl and benzyl azides and in a reaction of azidoferrocene with phenylacetylenes, respectively. The anticancer activity of the prepared compounds against hormone-dependent (MCF-7) and hormone-independent (HCC38) breast cancer cell lines was studied. The investigated compounds exhibited moderate anticancer activity against hormone-independent (IC50 ~ 15-48 μM) cancer cell line and low activity against hormone-dependent cancer cell line (IC50 ~ 84-98 μM).
- Plazuk, Damian,Rychlik, B?azej,B?auz, Andrzej,Domaga?a, S?awomir
-
p. 102 - 112
(2012/09/07)
-