117241-41-5Relevant academic research and scientific papers
Synthesis and local anesthetic activity of two homological series of diastereomeric phenylcarbamates
Gregan,kettmann,Novomesky,Polasek,Sivy
, p. 829 - 839 (2007/10/03)
By using stereospecific reactions we prepared two homological series of diastereomeric + cis- and + trans-N,N-dimethyl-2-(2-alkoxyphenylcarbamoyloxy)cyclohexylmethyl-ammo nium chlorides with number of carbons in the alkoxy group varying from one to eight. Structure of the prepared compounds was proved by NMR and IR spectroscopy. The principal physico-chemical characteristics, including partition coefficients, were obtained and relative local anesthetic activity was measured using a surface in vivo model. It was found that (1) for both cis- and trans-isomers there is a parabolic relationship between log activity and molecular lipophilicity (as measured by TLC R(M) and log P values), (2) all drugs prepared for this study use hydrophobic pathway to block inactivated channels, and (3) there is no strict requirement for precise disposition of the functional groups responsible for receptor binding, probably due to conformational flexibility of the sodium channel protein.
Stereocontrolled Syntheses of Mannich Bases and γ-Amino Alcohols
Risch, Nikolaus,Esser, Achim
, p. 233 - 238 (2007/10/02)
The reaction of enantiomerically pure SMP enamines 2 with iminium tetrachloroaluminates 3 yields optically active Mannich bases 4.Diastereoselective reduction of 4 gives γ-amino alcohols 5 with the desired configuration. Key Words: Mannich bases / Enamines / Iminium salts / γ-Amino alcohols
