Method for making debromohymenialdisine and analogs thereof

US6211361A · kind A · utility

Assignee

• State of Oregon acting by and through the State Board of Higher Ed. on Behalf of Oregon State Univ. · US

Inventors

• David Horne · Duarte, US
• Kenichi Yakushijin · New York, US

Key dates

• Filing date: Jul 20, 1999
• Grant date: Apr 3, 2001
• Expiry date: Jul 20, 2019

Classification

• Technology area (CPC A): Human Necessities
• CPC primary: A61P19/02
• WIPO field: Pharmaceuticals
• WIPO sector: Chemistry

Abstract

A method for making debromohymenialdisine (DBH) 2 and analogs thereof is described. One embodiment of the present method first comprises forming hymenin 4, and then converting hymenin into DBH 2 as described herein. One such embodiment first comprises providing a compound having Formula 3 ##STR1## where R is independently selected from the group consisting of hydrogen and lower aliphatic, and X is independently selected from the group consisting of hydrogen and halogen. A compound having Formula 3, such as Compound 10 with R and X as hydrogen, is then converted to DBH 2 or an analog thereof. An alternative embodiment of the method comprises forming Compound 30 or Compound 32, which are then directly converted to DBH 2. Alternatively, Compound 30 can be converted to Compound 10, which is then subsequently converted to DBH 2 by reaction with a halogen in the presence of an acid. The method of the present invention can be used to make analogs of DBH 2, including alkoxy derivatives, such as Compound 12, and conjugated diene derivatives, such as Compound 14.