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

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.

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 Creators:
Mann, Lea1, Author
Lang, Markus1, Author
Schulze, Philipp2, Author           
Halz, Jan Henrik3, Author
Csuk, René3, Author
Hoenke, Sophie3, Author
Seidel, Rüdiger W.1, Author
Richter, Adrian1, Author
Affiliations:
1Institut für Pharmazie, Martin-Luther-Universität Halle-Wittenberg, Wolfgang-Langenbeck-Str. 4, 06120, Halle (Saale), Germany, ou_persistent22              
2Service Department Schulze (GC, HPLC), Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445630              
3Institut für Chemie, Martin-Luther-Universität Halle-Wittenberg, Kurt-Mothes Str. 2, 06120, Halle (Saale), Germany, ou_persistent22              

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Free keywords: Amino acid; Phenylalanine amides; MMV688845; GSK1055950A; Racemization-free synthesis; Enantioselective activity; Antimycobacterial activity; Crystal structure
 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.

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Language(s): eng - English
 Dates: 2020-12-102021-07-142021-08-01
 Publication Status: Published in print
 Pages: 10
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1007/s00726-021-03044-1
 Degree: -

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Title: Amino Acids
  Abbreviation : Amino Acids
Source Genre: Journal
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Affiliations:
Publ. Info: Wien : Springer
Pages: - Volume / Issue: 53 (8) Sequence Number: - Start / End Page: 1187 - 1196 Identifier: ISSN: 0939-4451
CoNE: https://pure.mpg.de/cone/journals/resource/954925571881