The patent badge is an abbreviated version of the USPTO patent document. The patent badge does contain a link to the full patent document.
The patent badge is an abbreviated version of the USPTO patent document. The patent badge covers the following: Patent number, Date patent was issued, Date patent was filed, Title of the patent, Applicant, Inventor, Assignee, Attorney firm, Primary examiner, Assistant examiner, CPCs, and Abstract. The patent badge does contain a link to the full patent document (in Adobe Acrobat format, aka pdf). To download or print any patent click here.
Patent No.:
Date of Patent:
Mar. 08, 2011
Filed:
Mar. 17, 2006
Andrew G. Myers, Boston, MA (US);
Seth B. Herzon, New Haven, CT (US);
Jeremy Earle Wulff, Victoria, CA;
Romain Siegrist, Somerville, MA (US);
Jakub Svenda, Cambridge, MA (US);
Matthew Allen Zajac, Douglassville, PA (US);
Andrew G. Myers, Boston, MA (US);
Seth B. Herzon, New Haven, CT (US);
Jeremy Earle Wulff, Victoria, CA;
Romain Siegrist, Somerville, MA (US);
Jakub Svenda, Cambridge, MA (US);
Matthew Allen Zajac, Douglassville, PA (US);
President and Fellows of Harvard College, Cambridge, MA (US);
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.