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.
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.
Chang
H X
HX
Drug Development Laboratory, Department of Pharmacology, Toxicology & Therapeutics, The University of Kansas Medical Center, Kansas City, Kansas 66160-7419, USA.
Chou
T C
TC
Savaraj
N
N
Liu
L F
LF
Yu
C
C
Cheng
C C
CC
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