“Ring Breaker”: Neural Network Driven Synthesis Prediction of the Ring System Chemical Space

Thakkar, Amol; Selmi, Nidhal; Reymond, Jean-Louis; Engkvist, Ola; Bjerrum, Esben Jannik (2020). “Ring Breaker”: Neural Network Driven Synthesis Prediction of the Ring System Chemical Space. Journal of medicinal chemistry, 63(16), pp. 8791-8808. American Chemical Society 10.1021/acs.jmedchem.9b01919

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Ring systems in pharmaceuticals, agrochemicals, and dyes are ubiquitous chemical motifs. While the synthesis of common ring systems is well described and novel ring systems can be readily and computationally enumerated, the synthetic accessibility of unprecedented ring systems remains a challenge. “Ring Breaker” uses a data-driven approach to enable the prediction of ring-forming reactions, for which we have demonstrated its utility on frequently found and unprecedented ring systems, in agreement with literature syntheses. We demonstrate the performance of the neural network on a range of ring fragments from the ZINC and DrugBank databases and highlight its potential for incorporation into computer aided synthesis planning tools. These approaches to ring formation and retrosynthetic disconnection offer opportunities for chemists to explore and select more efficient syntheses/synthetic routes.

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