title: Design of antineoplastic agents based on the "2-phenylnaphthalene-type" structural pattern. 4. Synthesis and biological activity of 2-chloro-3-(substituted phenoxy)-1, 4-naphthoquinones and related 5,8-dihydroxy-1,4-naphthoquinones.
abstract: The intermediate in the preparation of 1,3,7, 10-tetrahydroxybenzo[b]naphtho[2,3-d]furan-6,11-dione (2), 2-chloro-5,8-dimethoxy-3-(3,5-dimethoxyphenoxy)-1,4-naphthoquinone (8h), and corresponding hydroxyl, methoxyl, and acetoxyl analogues was found to possess interesting inhibitory activities in a number of cytotoxic test systems. Activities were also noticed in some 5, 8-dihydroxy-1,4-naphthoquinone derivatives. A structure-activity discussion of compounds of this series is presented. The newly uncovered biological activity of 2-chloro-3-(substituted phenoxyl)-1, 4-naphthoquinones and 2,3-bis(substituted phenoxy)-1, 4-naphthoquinones may suggest an approach for the development of new classes of antineoplastic agents.
authors.affiliation: Drug Development Laboratory, Department of Pharmacology, Toxicology & Therapeutics, The University of Kansas Medical Center, Kansas City, Kansas 66160-7419, USA.
authors.forename: H X
authors.initials: HX
authors.lastname: Chang
authors.forename: T C
authors.initials: TC
authors.lastname: Chou
authors.forename: N
authors.initials: N
authors.lastname: Savaraj
authors.forename: L F
authors.initials: LF
authors.lastname: Liu
authors.forename: C
authors.initials: C
authors.lastname: Yu
authors.forename: C C
authors.initials: CC
authors.lastname: Cheng
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D015195:Drug Design; D009682:Magnetic Resonance Spectroscopy; D009281:Naphthalenes / Q000737:chemistry*; D009285:Naphthoquinones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013329:Structure-Activity Relationship