Synthesis of Mutual Azo Prodrugs of Anti-inflammatory Agents and Peptides Facilitated by α-Aminoisobutyric Acid

Reported is the synthesis of azo mutual prodrugs of the nonsteroidal anti-inflammatory agents (NSAIDs) 4-aminophenylacetic acid (4-APAA) or 5-aminosalicylic acid (5-ASA) with peptides, including an antibiotic peptide temporin analogue modified at the amino terminal by an α-aminoisobutyric acid (Aib)...

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Veröffentlicht in:	Journal of organic chemistry 2011-12, Vol.76 (23), p.9641-9647
Hauptverfasser:	Kennedy, David A, Vembu, Nagarajan, Fronczek, Frank R, Devocelle, Marc
Format:	Artikel
Sprache:	eng
Schlagworte:	Aminoisobutyric Acids - chemical synthesis Aminoisobutyric Acids - chemistry Aminoisobutyric Acids - pharmacology Anti-Bacterial Agents - chemical synthesis Anti-Bacterial Agents - chemistry Anti-Bacterial Agents - pharmacology Anti-Inflammatory Agents, Non-Steroidal - chemical synthesis Anti-Inflammatory Agents, Non-Steroidal - chemistry Anti-Inflammatory Agents, Non-Steroidal - pharmacology Antibiotics. Antiinfectious agents. Antiparasitic agents Azo Compounds - chemical synthesis Azo Compounds - chemistry Azo Compounds - pharmacology Biological and medical sciences Bones, joints and connective tissue. Antiinflammatory agents Chemistry Clostridium difficile - drug effects Exact sciences and technology General aspects Medical sciences Microbial Sensitivity Tests Molecular Structure Noncondensed benzenic compounds Organic chemistry Peptides Peptides - chemistry Peptides - pharmacology Pharmacology. Drug treatments Preparations and properties Prodrugs - chemical synthesis Prodrugs - chemistry Prodrugs - pharmacology
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Beschreibung
Zusammenfassung:	Reported is the synthesis of azo mutual prodrugs of the nonsteroidal anti-inflammatory agents (NSAIDs) 4-aminophenylacetic acid (4-APAA) or 5-aminosalicylic acid (5-ASA) with peptides, including an antibiotic peptide temporin analogue modified at the amino terminal by an α-aminoisobutyric acid (Aib) residue. These prodrugs are designed for colonic delivery of two agents to treat infection and inflammation by the bacterial pathogen Clostridium difficile.
ISSN:	0022-3263 1520-6904
DOI:	10.1021/jo201358e