1847-05-8Relevant academic research and scientific papers
Synthesis, molecular modeling, and selective inhibitory activity against human monoamine oxidases of 3-carboxamido-7-substituted coumarins
Chimenti, Franco,Secci, Daniela,Bolasco, Adriana,Chimenti, Paola,Bizzarri, Bruna,Granese, Arianna,Carradori, Simone,Yá?ez, Matilde,Orallo, Francisco,Ortuso, Francesco,Alcaro, Stefano
body text, p. 1935 - 1942 (2009/12/07)
A large series of 3-carboxamido-7-substituted coumarins have been synthesized and tested in vitro for their human monoamine oxidase A and B (hMAO-A and hMAO-B) inhibitory activity. Taking into account all the relevant structural information on MAOs reported in the literature, we made some changes in the coumarin nucleus and examined with particular attention the effect on activity and selectivity of substituting at position 3 with N-aryl or N-alkyl carboxamide and at position 7 with a benzyloxy or a 4'-F-benzyloxy group. Some of the assayed compounds proved to be potent, selective inhibitors of hMAO-B with IC50 values in the micromolar range. To better understand the enzyme-inhibitor interaction and to explain the selectivity of the most active compounds toward hMAOs, molecular modeling studies were carried out on new, high resolution, hMAO-A and hMAO-B crystallographic structures. ?2009 American Chemical Society.
ASYMMETRIC SYNTHESIS OF CYCLOALKANO-2,3-PIPERID-4-OLS
Grishina, G.V.,Potapov, V.M.,Gudasheva, T.A.
, p. 86 - 88 (2007/10/02)
A new method for the asymmetric synthesis of cycloalkano-2,3-piperid-4-ols by the reaction of a number of chiral enamino ketones with sodium borohydride is proposed.It is shown that the reduction proceeds via 1,4-hydride addition and leads to the formation of primarily one diastereomeric pair of cycloalkano-2,3-popiridols and their dehydration products.The asymmetric synthesis was confirmed by the production of optically active nitrogen-unsubstituted cycloalkano-2,3-piperid-4-ols when the chiral substituent was removed.
