Anthelmintic β-hydroxyketoamides (BKAs)

• Published in: Bioorganic & medicinal chemistry letters Vol. 8; no. 23; pp. 3317 - 3320
• Main Authors: Lee, Byung H., Clothier, Michael F., Dutton, Fred E., Conder, George A., Johnson, Sandra S.
• Format: Journal Article
• Language: English
• Published: Oxford Elsevier Ltd 01.12.1998; Elsevier
• Subjects: Animals; Anthelmintics - chemical synthesis; Anthelmintics - pharmacology; Antibiotics. Antiinfectious agents. Antiparasitic agents; Antiparasitic agents; Biological and medical sciences; Coumarins - chemical synthesis; Coumarins - pharmacology; Gerbillinae; Medical sciences; Pharmacology. Drug treatments; Haemonchus contortus; Anthelmintic; Ketoamide; Elimination; Enol; Oral administration; Lactone; Clearance; Chemotherapy; Experimental disease; Structure activity relation; Animal; Parasiticid; Helmintha; Carboxamide; Pyrimidine derivatives; Nemathelminthia; Bromine Organic compounds; Indene derivatives; Invertebrata; Pharmacokinetics; Chemical synthesis; Nematoda; Oxygen nitrogen heterocycle
• ISSN: 0960-894X; 1464-3405
• DOI: 10.1016/S0960-894X(98)00588-5

We have prepared several anthelmintic coumarins based on the β-hydroxyketoamide (BKA) template and have shown that this template remains valid over a wide range of changes to the coumarin moiety allowing for the inclusion of carbocyclic, bicyclic, and heterocyclic rings. Several anthelmintic BKAs were synthesized based on the core structure 2 to test our hypothesis from the lead compound 1. In our jird model these compounds showed good activity against Haemonchus contortus.