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Self-disproportionation of enantiomers and chirality-dependent halogen bond in N-C axially chiral quinazolinones

A halogen bond (abbreviated as XB) occurs when there is evidence of a net attractive interaction between an electrophilic region associated with a halogen atom in a molecular entity and a nucleophilic region in another, or the same, molecular entity.1) A typical XB is denoted by the three dots in R-XoooY. R-X is the XB donor, where X is any halogen atom with an electron-poor region, and R is a group covalently bound to X. Y is the XB acceptor and is typically a molecular entity possessing at least one electron-rich region. Since XB is highly directional interaction (the angle R-XoooY tends to be close to 180&deg;), it has been played an important role to control the organization of molecules in crystal engineering. Recently, XB donors have attracted much attention as bench-stable organo-Lewis acids in synthetic organic chemistry, and an increasing number of novel XB donors have been developed and reported to date. In addition, it has been identified that XB contributes to the recognition of the halogen-containing drug molecules in vivo, affecting their biological activities. In this symposium, the cutting-edge research of XB, including catalysis and medicinal chemistry, will be presented by the pioneering researchers in Japan, so that further understanding and utilization of XB interaction facilitate the development of drug discovery. 1) Definition of the halogen bond (IUPAC Recommendations 2013), G. R. Desiraju, P. S. Ho, L. Kloo, A. C. Legon, R. Marquardt, P. Metrangolo, P. Politzer, G. Resnati, K. Rissanen, Pure Appl. Chem. 2013, 85, 1711-1713.

Cutting-edge research of halogen bonding including catalysis and drug discovery

The 140th Annual Meeting of the Pharmaceutical Society of Japan (Kyoto)

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[S12-4]Self-disproportionation of enantiomers and chirality-dependent halogen bond in N-C axially chiral quinazolinones

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