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Polymorphism of an Nα-Aroyl-N-Aryl-Phenylalanine Amide: An X-ray and Electron Diffraction Study

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Goddard,  Richard
Service Department Lehmann (EMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Patzer,  Michael
Service Department Lehmann (EMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Lang, M., Goddard, R., Patzer, M., Ganapathy, U. S., Dick, T., Richter, A., et al. (2024). Polymorphism of an Nα-Aroyl-N-Aryl-Phenylalanine Amide: An X-ray and Electron Diffraction Study. Molbank, 2024(3): M1851. doi:10.3390/M1851.


Cite as: https://hdl.handle.net/21.11116/0000-000F-A951-7
Abstract
In view of the rise of drug-resistant tuberculosis and difficult-to-treat related diseases caused by non-tuberculous mycobacteria, there is an urgent need for antimycobacterial drug discovery. Nα-
aroyl-N-aryl-phenylalanine amides (AAPs) have been identified as antimycobacterial agents and are subject to lead optimization. The aim of the present study is to evaluate the impact of N-aryl ortho cyano substitution in a lead compound on the crystal and molecular structure and its in vitro activity
against Mycobacterium abscessus. The title AAP can be conveniently synthesized from N-Boc-protected D-phenylalanine in two amide coupling steps using a previously established racemization-free method. Two polymorphic forms in the solid-state are described, as discovered by X-ray and electron diffraction. The introduction of a cyano group in the ortho position of the AAP N-aryl ring, however, leads to loss of in vitro activity against M. abscessus subsp. abscessus.