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Benzylguanidines and other galegine analogues inducing weight loss in mice

Coxon, Geoffrey D. and Furman, Brian L. and Harvey, Alan L. and McTavish, John and Mooney, Mark H. and Arastoo, Mahmoud and Kennedy, A.R. and Tettey, J.N.A. and Waigh, R.D. (2009) Benzylguanidines and other galegine analogues inducing weight loss in mice. Journal of Medicinal Chemistry, 52 (11). pp. 3457-3463. ISSN 0022-2623

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Abstract

Dimethylallylguanidine, also known as galegine, isolated from Galega officinalis, has been shown to have weight reducing properties in vivo. Substitution of the guanidine group with an N-cyano group and replacement of guanidine with amidine, pyrimidine, pyridine, or the imidazole moieties removed the weight reducing properties when evaluated in BALB/c mice. However, retention of the guanidine and replacement of the dimethylallyl group by a series of functionalized benzyl substituents was shown to exhibit, and in some cases significantly improve, the weight reducing properties of these molecules in BALB/c, ob/ob, and diet induced obesity (DIO) mice models. The lead compound identified, across all models, was 1-(4-chlorobenzyl)guanidine hemisulfate, which gave an average daily weight difference (% from time-matched controls; +/- SEM) of -19.7 +/- 1.0, -11.0 +/- 0.7, and -7.3 +/- 0.8 in BALB/c, ob/ob, and DIO models, respectively.