Racemization-free synthesis of 
Nα-2-thiophenoyl-phenylalanine-2-morpholinoanilide enantiomers and their 
antimycobacterial activity

Mann, Lea; Lang, Markus; Schulze, Philipp; Halz, Jan Henrik; Csuk, René; Hoenke, Sophie; Seidel, Rüdiger W.; Richter, Adrian

doi:10.1007/s00726-021-03044-1

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Racemization-free synthesis of Nα-2-thiophenoyl-phenylalanine-2-morpholinoanilide enantiomers and their antimycobacterial activity

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Schulze, Philipp
Service Department Schulze (GC, HPLC), Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Mann, L., Lang, M., Schulze, P., Halz, J. H., Csuk, R., Hoenke, S., et al. (2021). Racemization-free synthesis of Nα-2-thiophenoyl-phenylalanine-2-morpholinoanilide enantiomers and their antimycobacterial activity. Amino Acids, 53(8), 1187-1196. doi:10.1007/s00726-021-03044-1.

Cite as: https://hdl.handle.net/21.11116/0000-0008-F38E-6

Abstract

Nα-2-thiophenoyl-d-phenylalanine-2-morpholinoanilide (MMV688845, IUPAC: N-(1-((2-morpholinophenyl)amino)-1-oxo-3-phenylpropan-2-yl)thiophene-2-carboxamide) from the Pathogen Box^® library (Medicines for Malaria Ventures, MMV) is a promising lead compound for antimycobacterial drug development. Two straightforward synthetic routes to the title compound starting from phenylalanine or its Boc-protected derivative are reported. Employing Boc-phenylalanine as starting material and the T3P^® and PyBOP^® amide coupling reagents enables racemization-free synthesis, avoiding the need for subsequent separation of the enantiomers. The crystal structure of the racemic counterpart gives insight into the molecular structure and hydrogen bonding interactions in the solid state. The R-enantiomer of the title compound (derived from d-phenylalanine) exhibits activity against non-pathogenic and pathogenic mycobacterial strains, whereas the S-enantiomer is inactive. Neither of the enantiomers and the racemate of the title compound shows cytotoxicity against various mammalian cells.