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 dias...

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Bibliographic Details
Published in:Journal of medicinal chemistry 1994-03, Vol.37 (5), p.710-712
Main Authors: Benedetti-Doctorovich, Violeta, Burgess, Edward M, Lambropoulos, John, Lednicer, Daniel, Van Derveer, Donald, Zalkow, Leon H
Format: Article
Language:English
Subjects:
Antineoplastic Agents - chemical synthesis
Antineoplastic Agents - chemistry
Antineoplastic Agents - therapeutic use
Chemistry
Condensed matter: structure, mechanical and thermal properties
Crystallography, X-Ray
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms
Humans
Imines - chemical synthesis
Imines - chemistry
Imines - therapeutic use
Molecular Structure
Organic chemistry
Organic compounds
Oxazoles - chemical synthesis
Oxazoles - chemistry
Oxazoles - therapeutic use
Physics
Preparations and properties
Stereoisomerism
Structure of solids and liquids
crystallography
Structure of specific crystalline solids
Tumor Cells, Cultured
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Summary: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.
ISSN:0022-2623
1520-4804
DOI:10.1021/jm00031a023