Isomeric phenylthioimidazo[1,2-a]pyridines as anthelmintics

A series of isomeric imidazo[1,2-alpha]pyridine-2-carbamates was prepared for testing as anthelmintics. The analogues were synthesized by reacting the appropriate 2-aminopyridine and methyl chloroacetylcarbamate. Steric hindrance in the 2,6-disubstituted derivative resulted in the formation of the i...

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Bibliographic Details
Published in:	Journal of medicinal chemistry Vol. 24; no. 12; pp. 1483 - 1487
Main Authors:	Bochis, Richard J, Olen, Leonard E, Fisher, M. H, Reamer, Robert A, Wilks, George, Taylor, Joyce E, Olson, George
Format:	Journal Article
Language:	English
Published:	United States American Chemical Society 01-12-1981
Subjects:	Animals Anthelmintics - chemical synthesis Carbamates - chemical synthesis Carbamates - pharmacology Chemical Phenomena Chemistry Imidazoles - chemical synthesis Imidazoles - pharmacology Isomerism Mice Nematode Infections - drug therapy
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Summary:	A series of isomeric imidazo[1,2-alpha]pyridine-2-carbamates was prepared for testing as anthelmintics. The analogues were synthesized by reacting the appropriate 2-aminopyridine and methyl chloroacetylcarbamate. Steric hindrance in the 2,6-disubstituted derivative resulted in the formation of the isomeric 3-substituted analogue as the major product. Carbon-13 NMR proved useful in the structural assignments in this series. None of the analogues exhibited the potency of methyl 6-(phenylsulfinyl)imidazo[1,2-alpha]pyridine-2-carbamate when tested against Nematospiroides dubius in mice.
Bibliography:	ark:/67375/TPS-FB31XSN5-R istex:8E03590128BE37BA08CB9BF5DFA2A89844724C09 ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23
ISSN:	0022-2623 1520-4804
DOI:	10.1021/jm00144a022