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

Amino Acids. 2001;20(2):135-44. doi: 10.1007/s007260170054.

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)-alpha-amino acids la-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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acids / chemical synthesis*
  • Amino Acids / chemistry
  • Benzoquinones / chemistry*
  • Biochemistry / methods*
  • Lactones / chemistry*
  • Magnetic Resonance Spectroscopy
  • Molecular Structure

Substances

  • Amino Acids
  • Benzoquinones
  • Lactones
  • quinone