1-Naphthalenecarboxamide, 4-[(5S)-5-[3-chloro-4-fluoro-5-(trifluoromethyl)phenyl]-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-[2-oxo-2-[(2,2,2-trifluoroethyl)amino]ethyl]-

Uses

umifoxolaner (ML-878) is a γ-aminobutyric acid (GABA) regulated chloride channels antagonist. Umifoxolaner is an anti-parasitic agent[1].

Production Methods

The synthesis of umifoxolaner involves constructing a chiral isoxazoline ring system and attaching multiple fluorinated aromatic groups to enhance its lipophilicity and target specificity. The process begins with a [3+2] cycloaddition reaction to form the (5S)-configured isoxazoline core, which is then functionalised with a 3-chloro-4-fluoro-5-(trifluoromethyl)phenyl group and a second trifluoromethyl substituent to boost metabolic stability and receptor binding. Separately, a naphthalene-1-carboxamide moiety is synthesised and linked via an amide bond to a difluoroethylamino-oxoethyl side chain, completing the pharmacophore.

Mechanism of action

A gamma-aminobutyric acid (GABA) regulated chloride channels antagonist

References

[1] Cady, Susan Mancini; Cheifetz, Peter; Galeska, Izabela; Le Hir de Fallois, Loic.Long-acting injectable formulations comprising isoxazoline for prevention and treatment of parasitic infections.WO2016164487A1.

Pesticide Type

Acaricide; Insecticide; Veterinary substance