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Reduced Itraconazole Concentration and Durations Are Successful in Treating Batrachochytrium dendrobatidis Infection in Amphibians

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Benzylated 1,2,3-triazoles as anticoccidiostats.

R J Bochis¹, J C Chabala, E Harris

¹Merck Sharp and Dohme Research Laboratories, Rahway, New Jersey 07065-0900.

Journal of Medicinal Chemistry

|September 1, 1991

Summary

Researchers synthesized novel 5-amino-4-carbamoyl-1,2,3-triazoles for anticoccidial activity. Compound L-651,582 showed high efficacy but had residue issues, with its mechanism involving host cell calcium entry, not IMP dehydrogenase inhibition.

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Area of Science:

Medicinal Chemistry
Parasitology
Pharmacology

Background:

Coccidiosis remains a significant challenge in poultry farming, necessitating the development of new therapeutic agents.
The 5-amino-4-carbamoyl-1,2,3-triazole scaffold represents a promising structural class for antiparasitic drug discovery.

Purpose of the Study:

To synthesize and evaluate a series of substituted 5-amino-4-carbamoyl-1,2,3-triazoles for in vivo anticoccidial activity.
To investigate the structure-activity relationships and mechanism of action of potent compounds within this series.

Main Methods:

Two distinct synthetic routes were employed to prepare substituted 5-amino-4-carbamoyl-1,2,3-triazoles.
In vivo anticoccidial efficacy was assessed against Eimeria species in chickens.
Mechanistic studies were conducted to elucidate the mode of action, including assays for IMP dehydrogenase inhibition and host cell calcium entry.

Main Results:

A library of 5-amino-4-carbamoyl-1,2,3-triazoles (3a-w) was successfully synthesized.
Compound L-651,582 (3a) demonstrated potent anticoccidial activity against field isolates of Eimeria.
Mechanistic studies indicated that L-651,582 interferes with host cell calcium entry, distinct from IMP dehydrogenase inhibition.

Conclusions:

The 5-amino-4-carbamoyl-1,2,3-triazole scaffold is a viable platform for developing anticoccidial agents.
L-651,582 exhibits promising efficacy but was limited by tissue residues.
The novel mechanism of action involving calcium entry warrants further investigation for therapeutic potential in coccidiosis and other diseases.