Novel N-quinonyl amino acids and their transformation to 3-substituted p-isoxazinones.
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.
Gorohovsky
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Department of Chemistry, Ben-Gurion University of the Negev, Beer-sheva, Israel. bittner@bgumail.bgu.ac.il
Bittner
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D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D016227:Benzoquinones / Q000737:chemistry*; D001671:Biochemistry / Q000379:methods*; D007783:Lactones / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure
D000596:Amino Acids; D016227:Benzoquinones; D007783:Lactones; C004532:quinone