Enterobactin compounds

US5412080A · kind A · utility

Assignee

• President and Fellows of Harvard College · US

Inventors

• Yoshito Kishi · Cambridge, US
• Bruno Tse · Philadelphia, US

Key dates

• Filing date: Aug 25, 1993
• Grant date: May 2, 1995
• Expiry date: Aug 25, 2013

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07D493/18
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

Enterobactin analogs prepared from scyllo-inositol mono-orthoformate and having the following formula: ##STR1## wherein each X.sub.1, X.sub.2 and X.sub.3, independently, is H, C.sub.1-20 alkyl, phenyl, naphthyl, C.sub.7-20 aralkyl, or C.sub.7-20 alkaryl; Y is H, C.sub.1-20 alkyl, phenyl, naphthyl; C.sub.7-20 aralkyl, C.sub.7-20 alkaryl; --(C.sub.p H.sub.2p)--CH.sub.2 OH, --(C.sub.p H.sub.2p)--COOH or its salt, --(C.sub.p H.sub.2p)--NR.sub.1.R.sub.2 or its salt, or --(C.sub.p H.sub.2p)--N.sup.+ R.sub.1.R.sub.2.R.sub.3 ; in which p is 1-20 and each R.sub.1, R.sub.2 and R.sub.3, independently, is H or C.sub.1-5 alkyl; and m, n and o, independently, is 1-6; or the enantiomer thereof.