89074-22-6Relevant academic research and scientific papers
Benzylguanidines and other galegine analogues inducing weight loss in mice
Coxon, Geoffrey D.,Furman, Brian L.,Harvey, Alan L.,McTavish, John,Mooney, Mark H.,Arastoo, Mahmoud,Kennedy, Alan R.,Tettey, Justice M.,Waigh, Roger D.
supporting information; experimental part, p. 3457 - 3463 (2010/03/25)
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.
ACTIVATING ACTION OF THE IMMONIUM GROUP IN THE SUBSTITUTION OF ALKOXYL AND HALOGEN ATOMS BY THE ALKYLAMINO GROUP IN THE BENZENE RING
Yudin, L. G.,Blokhin, A. V.,Bundel', Yu. G.,Simkin, B. Ya.,Terenin, V. I.
, p. 2064 - 2068 (2007/10/02)
The substitution of the alkoxy group in o-, p-, and m-alkoxybenzylidenedimethylimmonium iodides by the action of aliphatic amines was investigated.Only p-alkoxy derivatives enter into the reaction forming, after hydrolysis, p-alkyl- and p-dialkylaminobenzaldehydes.Substitution can also be realized in p-alkoxybenzaldehydes and Schiff bases in the presence of the amine hydrochloride.Similarly, the halogen atom in p-halogenobenzaldehydes is substituted by the aliphatic amine residue.Quantum-mechanical calculations of the energy of anionic localization and charge at the attacked carbon atom o f the benzene ring are consistent with the experimantal data.
