Novel N-quinonyl amino acids and their transformation to 3-substituted p-isoxazinones

S. Gorohovsky, S. Bittner

Research output: Contribution to journalArticlepeer-review

16 Scopus citations

Abstract

Quinonyl amino acids are building blocks in the preparation of peptides which target the quinonic drug to cancer damaged area. Novel N-(3-chloro-1,4-dihydro-1,4-dioxonaphthalen-2-yl)-α-amino acids 1a-f were prepared by direct substitution of 2,3-dichloro-1,4-naphthoquinone. The quinonic moiety was reduced by NaBH4 to yield the corresponding hydroquinones 2a-f, which in acidic conditions underwent internal cyclization to yield the 3,4-dihydro-2H-naphth[1,2-b]-1,4-oxazine-2-ones (six-membered azlactones) 3a-f.

Original languageEnglish
Pages (from-to)135-144
Number of pages10
JournalAmino Acids
Volume20
Issue number2
DOIs
StatePublished - 1 Jan 2001

Keywords

  • Amino acids
  • Azlactones
  • Hydroquinones
  • Isoxazinones
  • Quinones

Fingerprint

Dive into the research topics of 'Novel N-quinonyl amino acids and their transformation to 3-substituted p-isoxazinones'. Together they form a unique fingerprint.

Cite this