Analgesic dipeptide derivatives. Part 8. 3-Amino-2-hydroxy-4-[2-(o-nitrophenylthio)indol-3-yl]butanoic acid [AH(Nps)IBA]-containing dipeptide analogues of the analgesic compound H-Trp(Nps)-Lys-OMe

@article{Herranz1991AnalgesicDD,
  title={Analgesic dipeptide derivatives. Part 8. 3-Amino-2-hydroxy-4-[2-(o-nitrophenylthio)indol-3-yl]butanoic acid [AH(Nps)IBA]-containing dipeptide analogues of the analgesic compound H-Trp(Nps)-Lys-OMe},
  author={Rosario Herranz and Soledad Vinuesa and Concepci{\'o}n P{\'e}rez and Ma Teresa Garc{\'i}a-L{\'o}pez and Marı́a L de Ceballos and Joaquı́n Del Rı́o},
  journal={Journal of The Chemical Society-perkin Transactions 1},
  year={1991},
  pages={2749-2755}
}
A series of diastereoisomeric dipeptides, analogues of the analgesic compound H-Trp(Nps)Lys-OMe, containing 3-amino-2-hydroxy-4-(2-(o-nitrophenylthio)indol-3-yl]butanoic acid [AH(Nps)IBA) and Lys or Leu has been synthesized. These compounds were tested as aminopeptidase-M and -B (AP-M and AP-B) inhibitors and as analgesics. The AH(Nps)IBA-Leu dipeptides, independently of their stereochemistry, were poor inhibitors of AP-M and AP-B, with IC50-values in the 10–4 mol dm–3 range, while the AH(Nps… 
1 Citations
Pyrazine alkaloids via dimerization of amino acid-derived α-amino aldehydes: biomimetic synthesis of 2,5-diisopropylpyrazine, 2,5-bis(3-indolylmethyl)pyrazine and actinopolymorphol C.
TLDR
This methodology demonstrates the viability of a recently proposed, alternative biosynthetic route to 2,5-disubstituted pyrazine natural products in nature and describes a novel, concise approach to pyrazines from α-amino aldehydes derived from readily available, cheap amino acids.

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