Synthesis of avrainvillamide, strephacidin B, and analogues thereof
US7902196B2 · kind B2 · utility
Assignee
Inventors
Key dates
| Filing date | Mar 17, 2006 |
| Grant date | Mar 8, 2011 |
| Priority date | — |
| Expiry date | Aug 26, 2026 |
Classification
- Technology area (CPC C)Chemistry; Metallurgy
- CPC primaryC07D495/22
- WIPO fieldOrganic fine chemistry
- WIPO sectorChemistry
Abstract
The syntheses of the natural products, avrainvillamide and stephacidin B, are provided. The α,β-unsaturated nitrone functionality of avrainvillamide and its 3-alkylidene-3H-indole 1-oxide core is shown to covalently and reversibly bond to heteroatom-based nucleophiles. This capability may allow these molecules to bind active site nucleophiles and may provide the basis for designing potent and selective enzyme inhibitors. Both avrainvillamide and its dimer stephacidin B have been reported to exhibit antiproliferative activity, and avrainvillamide has been reported to exhibit antimicrobial activity against multi-drug resistant bacteria. Avrainvillamide has been found to target cytoskeleton-linking membrane protein (CLIMP-63) thereby preventing cells from undergoing mitosis. The invention provides syntheses of these natural products as well as analogs of these natural products and their functional cores. The compounds of the invention may be used in the treatment of diseases such as cancer, autoimmune diseases, and bacterial infection.
Source: USPTO / EPO open patent data. Objective bibliographic and citation counts.