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US 6,673,937 B2Granted
Syntheses and methods of use of new antimitotic agents
AssigneeUniversity of Pittsburgh
InventorsJohn S. Lazo, Peter Wipf, Billy W. Day
Life of this patent
Estimating the term…
Abstract
Oxidative cyclization of bis-naphthyl ethers allows concise total syntheses of palmarumycin CP1 and deoxypreussomerin A in 8-9 steps and 15-35% overall yield from 5-hydroxy-8-methoxy-1-tetralone. A small library of palmarumycin analogs was created. Biological evaluation of these naphthoquinone spiroketals against MCF-7 and MDA-MB-231 human breast cancer cells revealed several low-micromolar growth inhibitors. A number of the analogs inhibit the thioredoxin—thioredoxin reductase system.
Claims2
A compound of the structural formula
- wherein r is a member selected from the group consisting of (e)-HC=CHPh, (e)-hc=CHMe, n-C5H11, (e)-CH2HC=CHEt, (m)-MeOPH, benzonitrile, 2-furyl, (E,E)-HC=C(ME)CH2CH2CH=CMe2, 3-furyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, and HC=CH2.
A compound of the structural formula
- wherein R is a member selected from the group consisting of (p)-MeOPh, C(Me)=CH2, C==H, (p)-BrPh, (p)-ClPh, 2-furyl(5-(p)-BrPh), 2-furyl(5-(o)-ClPh), 2-furyl(5-(m)-ClPh), 2-furyl(5-(o)-CF3Ph), 2-furyl(5-(m)-CF3Ph), HC=CMe2, (E)-C(Me)=CHMe, and (Z)C(Me)=-CHMe.
Dependencies are inferred from the claim text.