Synthesis and use of .beta.-lapachone analogs
US5763625A · kind A · utility
Assignee
Inventors
Key dates
| Filing date | Apr 25, 1995 |
| Grant date | Jun 9, 1998 |
| Priority date | — |
| Expiry date | Apr 25, 2015 |
Classification
- Technology area (CPC C)Chemistry; Metallurgy
- CPC primaryC07D311/92
- WIPO fieldOrganic fine chemistry
- WIPO sectorChemistry
Abstract
3-Substituted-.beta.-lapachone analogs and their use either alone or to augment chemotherapy or radiotherapy to induce programmed neoplastic cell death without exhibiting toxicity to surrounding normal cells are disclosed. In particular, 3-allyl-.beta.-lapachones, 3-alkyl-.beta.-lapachones and 3-halo-.beta.-lapachones were found to be Topoisomerase (Topo I) inhibitors. When these analogs are used alone there is a reversible single-strand break in the DNA of neoplastic cells causing apoptosis and cell death in some cells. However, when these analogs are combined with chemotherapy or X-irradiation, an irreversible Topo I-mediated break is achieved. A new and more efficient chemical synthesis of the compounds is also disclosed.
Source: USPTO / EPO open patent data. Objective bibliographic and citation counts.