Design, synthesis and biological evaluation of simplified analogues of MraY inhibitory natural product with rigid scaffold

Exploring novel aryl/heteroaryl-isosteres of phenylthiazole against multidrug-resistant bacteria

“…4.1.1. Preparation of sulfonamide intermediates (19)(20)(21)(22)(23)(24)(25). To a solution of 5-bromothiophene-2-sulfonyl chloride (0.13 g, 0.5 mmol) in dichloromethane (0.67 M), an appropriate amine (0.75 mmol) and triethylamine (0.1 g, 1 mmol) were added.…”

Electrosynthesis of Artificial Peptides and Nucleosides via the Nitromethane–Lithium Perchlorate Electrolyte System: A Review

“…Some C ‐azanucleosides with β‐anomer configuration have been approved as pharmaceutical agents for the treatment of cancer or viral infection; thus, we attempted the stereoselective synthesis of C ‐azanucleosides. Precedent studies by Ichikawa and Matsuda reported that 2’,3’‐ O ‐pentylidene acetal protection on ribose scaffolds exhibited complete stereoselectivity in the Lewis‐acid–mediated glycosidation reaction, and broad‐substrate scope was demonstrated in their synthesis of a natural product and its analogues [70–72] …”

“…Precedent studies by Ichikawa and Matsuda reported that 2',3'-O-pentylidene acetal protection on ribose scaffolds exhibited complete stereoselectivity in the Lewis-acid-mediated glycosidation reaction, and broad-substrate scope was demonstrated in their synthesis of a natural product and its analogues. [70][71][72] From these backgrounds, we attempted the stereoselective synthesis of C-azanucleosides by designing pentylidene acetalprotected prolinol 31 (Scheme 13), which was readily available from D-ribonolactone. [73] The electrochemical N-α hydroxylation gave 32, and continuous deoxygenative fluorination by N,Ndiethylaminosulfur trifluoride (DAST) gave fluorosugar 33.…”

A Sub-Micromolar MraYAA Inhibitor with an Aminoribosyl Uridine Structure and a (S,S)-Tartaric Diamide: Synthesis, Biological Evaluation and Molecular Modeling

“…The synthesis of analogs of these peptidonucleosidic compounds has been the matter of intensive synthetic work [ 19 , 20 , 21 , 22 ], especially regarding the goal of decreasing their complexity while maintaining potent inhibition of MraY enzymatic activity. This is particularly challenging, considering the hydrophilicity of these molecules, and interesting progress has been achieved towards this objective [ 23 , 24 , 25 , 26 , 27 ]. Based on the aminoribosyluridine skeleton known to be important for MraY inhibition, we developed the synthesis of several families of simplified analogs ( Figure 2 A), with the chemical diversity being introduced on this scaffold through a triazole [ 28 ] or a methylene triazole [ 29 ] linker.…”