Synthesis of 2-methyl-(Z)-4-(phenylimino)naphth[2,3-d]oxazol-9-one , a monoimine quinone with selective cytotoxicity toward cancer cells.
A regio and stereospecific synthesis of 2-methyl-(Z)-4-(phenylimino)naphth[2,3-d]oxazol-9-one (1) was achieved by using titanium tetrachloride in methylene chloride in the preparation of the imine. The regiochemistry was assigned by single-crystal X-ray analysis. In vitro tests showed that this diastereomer is selectively active for some solid cancer tumors.
Benedetti-Doctorovich
V
V
School of Chemistry and Biochemistry, Georgia Institute of Technology, Atlanta 30332.
Burgess
E M
EM
Lambropoulos
J
J
Lednicer
D
D
Van Derveer
D
D
Zalkow
L H
LH
D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000627:therapeutic use; D018360:Crystallography, X-Ray; D006801:Humans; D007097:Imines / Q000138:chemical synthesis* / Q000737:chemistry / Q000627:therapeutic use; D015394:Molecular Structure; D010080:Oxazoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000627:therapeutic use; D013237:Stereoisomerism; D014407:Tumor Cells, Cultured
D000970:Antineoplastic Agents; D007097:Imines; D010080:Oxazoles; C086220:2-methyl-4-(phenylimino)naphth(2,3-d)oxazol-9-one