Practical One-Pot Syntheses of Regioisomeric Furan-Fused Pyridinones (and Quinolinones) from Common Precursors

Delaunay, Thierry; Conreaux, David; Bossharth, Emmanuel; Desbordes, Philippe; Monteiro, Nuno; Balme, Geneviève

doi:10.1055/s-0029-1218692

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2024

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“…With the optimized conditions of step a and step b in hand, we began screening the conditions for step c. A preliminary screening was conducted to investigate the reaction conditions of cyclization step mentioned in the literature [17–21] . However, product 1 was not detected under most of the tested reaction conditions.…”

Section: Resultsmentioning

confidence: 99%

Optimization of the synthesis of BET BD2 selective inhibitor XY153

Zhu,

Li,

Dong

et al. 2024

Chemistry & Biodiversity

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XY153 is a promising BET BD2 inhibitor with an IC50 value of 0.79 nM against BRD4 BD2. It shows 354‐fold selectivity over BRD4‐BD1 and 6‐fold selectivity over other BET BD2 domains. However, the reported synthesis route of XY153 and its derivatives are extremely poor‐yielding. After the synthesis of three key fragments, XY153 can only be obtained with a yield of 1.3% in the original four‐step reaction. In this study, we reported a three‐step alternative route in the synthesis process of XY153. The reaction conditions for this route were thoroughly investigated and optimized, resulting in a significantly improved yield of 61.5%. This efficient synthesis route establishes a robust chemical foundation for the rapid synthesis of XY153 derivatives as BET BD2 inhibitors in the near future.

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Section: Resultsmentioning

confidence: 99%