A Collection of Robust Organic Synthesis Reactions for In Silico Molecule Design

• Published in: Journal of chemical information and modeling Vol. 51; no. 12; pp. 3093 - 3098
• Main Authors: Hartenfeller, Markus, Eberle, Martin, Meier, Peter, Nieto-Oberhuber, Cristina, Altmann, Karl-Heinz, Schneider, Gisbert, Jacoby, Edgar, Renner, Steffen
• Format: Journal Article
• Language: English
• Published: Washington, DC American Chemical Society 27.12.2011
• Subjects: Biological and medical sciences; Chemical Information; Chemical reactions; Chemistry Techniques, Synthetic - methods; Collaboration; Comparative analysis; Computer-Aided Design; Databases, Factual; Drug Design; General pharmacology; Medical sciences; Molecules; Pharmaceutical technology. Pharmaceutical industry; Pharmacology. Drug treatments; R&D; Research & development; Assembly line; Legibility; Relevance; Organic synthesis; Computational chemistry; Screening; Chemical reaction; Ring; Pharmaceutical industry; Overlay; Chemical synthesis; Secondary metabolism; Intelligent system; Organic compounds
• ISSN: 1549-9596; 1549-960X; 1549-960X
• DOI: 10.1021/ci200379p

A focused collection of organic synthesis reactions for computer-based molecule construction is presented. It is inspired by real-world chemistry and has been compiled in close collaboration with medicinal chemists to achieve high practical relevance. Virtual molecules assembled from existing starting material connected by these reactions are supposed to have an enhanced chance to be amenable to real chemical synthesis. About 50% of the reactions in the dataset are ring-forming reactions, which fosters the assembly of novel ring systems and innovative chemotypes. A comparison with a recent survey of the reactions used in early drug discovery revealed considerable overlaps with the collection presented here. The dataset is available encoded as computer-readable Reaction SMARTS expressions from the Supporting Information presented for this paper.