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US 7,247,701 B2Granted
Amino amides, peptides and peptidomimetics
AssigneeUniversity of Southern California
InventorsNicos A. Petasis, Xin Yao
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Abstract
Synthetic methods and compounds involving amino amides, peptides and peptidomimetics. Amino amide derivatives are prepared via the one-step three-component reaction of a glyoxamide, an amine, and an organoboron derivative. Conversion of the product to another glyoxamide intermediate allows the iterative use of this chemistry for the synthesis of peptides and peptidomimetics.
Claims11
A method for preparing a compound represented by formula 5:
- comprising the steps of:
- (a) converting a compound represented by formula 1 to a compound represented by formula 2:
- (b) reacting the compound of formula 2 with an amine derivative represented by formula 3 and an organoboron compound represented by formula 4:
- thereby forming the compound represented by formula 5,
- wherein:
- R1 and R2 are independently selected from the group consisting of hydrogen, alkyl, allyl, alkenyl, aryl, heteroaryl, acyl, sulfonyl, amino, alkylamino, dialkylamino, acylamino, sulfonylamino, and alkoxy, provided that R1 and R2 can be connected together forming a ring;
- or R2 is a group represented by the following formula:
- wherein:
- A1 and A2 are independently selected from the group consisting of hydrogen, alkyl, allyl, alkenyl, aryl, heteroaryl, acyl, sulfonyl, amino, alkylamino, dialkylamino, acylamino, sulfonylamino, alkoxy, an amino acid and a peptide;
- A3 is alkyl, aryl, heteroaryl, allyl, alkenyl, alkynyl, or allenyl;
- and
- R1, A1, A2 and A3 are optionally connected to form one or more rings;
- Rw is hydrogen, alkyl, aryl, or heteroaryl;
- Ra and Rb are independently selected from the group consisting of hydrogen, alkyl, allyl, benzyl, aryl, heteroaryl, acyl, sulfonyl, amino, alkylamino, dialkylamino, acylamino, sulfonylamino, and alkoxy, provided that Ra and Rb can be joined together forming a ring;
- or Ra is hydrogen, alkyl, allyl, alkenyl, aryl, heteroaryl, acyl, sulfonyl, amino, alkylamino, dialkylamino, acylamino, sulfonylamino, or alkoxy and Rb is
- wherein R12 is selected from the group consisting of hydrogen, alkyl, alkenyl, aryl, heteroaryl, amino, alkylamino, dialkylamino, hydroxyamino, alkoxyamino, hydroxyl, alkoxy, aryloxy and heteroaryloxy;
- R3 and R11 are independently alkyl, aryl, heteroaryl, allyl, alkenyl, alkynyl, or allenyl;
- provided that Ra, R11 and R12 can be connected together forming one or more rings and
- X and Y are independently selected from the group consisting of hydroxy, alkoxy, aryloxy, amino, alkylamino, and dialkylamino, provided that X and Y can be joined together forming a ring.
16 more elements
Dependencies are inferred from the claim text.