144222-22-0Relevant articles and documents
Efficient and scalable method for the selective alkylation and acylation of secondary amines in the presence of primary amines
Laduron, Frederic,Tamborowski, Vanessa,Moens, Luc,Horvath, Andras,De Smaele, Dirk,Leurs, Stef
, p. 102 - 104 (2005)
Selective substitution of secondary amines in the presence of primary amines is performed by using the reaction solvent, methyl isobutylketone (MIBK), as a temporary protecting group for the primary amine. After acylation or alkylation of the secondary amine, the resulting imine intermediate is smoothly hydrolysed, leading to the free primary amine in high yield and purity. This procedure represents a cheap and scalable alternative to multistep methods requiring several protections and deprotections.
Antimalarial agents against both sexual and asexual parasites stages: structure-activity relationships and biological studies of the Malaria Box compound 1-[5-(4-bromo-2-chlorophenyl)furan-2-yl]-N-[(piperidin-4-yl)methyl]methanamine (MMV019918) and analogues
Vallone, Alessandra,D'Alessandro, Sarah,Brogi, Simone,Brindisi, Margherita,Chemi, Giulia,Alfano, Gloria,Lamponi, Stefania,Lee, Soon Goo,Jez, Joseph M.,Koolen, Karin J.M.,Dechering, Koen J.,Saponara, Simona,Fusi, Fabio,Gorelli, Beatrice,Taramelli, Donatella,Parapini, Silvia,Caldelari, Reto,Campiani, Giuseppe,Gemma, Sandra,Butini, Stefania
, p. 698 - 718 (2018/03/24)
Therapies addressing multiple stages of Plasmodium falciparum life cycle are highly desirable for implementing malaria elimination strategies. MMV019918 (1, 1-[5-(4-bromo-2-chlorophenyl)furan-2-yl]-N-[(piperidin-4-yl)methyl]methanamine) was selected from the MMV Malaria Box for its dual activity against both asexual stages and gametocytes. In-depth structure-activity relationship studies and cytotoxicity evaluation led to the selection of 25 for further biological investigation. The potential transmission blocking activity of 25 versus P. falciparum was confirmed through the standard membrane-feeding assay. Both 1 and 25 significantly prolonged atrioventricular conduction time in Langendorff-isolated rat hearts, and showed inhibitory activity of Ba2+ current through Cav1.2 channels. An in silico target-fishing study suggested the enzyme phosphoethanolamine methyltransferase (PfPMT) as a potential target. However, compound activity against PfPMT did not track with the antiplasmodial activity, suggesting the latter activity relies on a different molecular target. Nevertheless, 25 showed interesting activity against PfPMT, which could be an important starting point for the identification of more potent inhibitors active against both sexual and asexual stages of the parasite.
N,N'-2,4-DIANILINOPYRIMIDINE DERIVATIVES, PREPARATION THEREOF AS DRUGS, PHARMACEUTICAL COMPOSITIONS ESSENTIALLY AS IKK INHIBITORS
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Page/Page column 48, (2010/04/30)
The disclosure relates to a compound of formula (I): wherein R, R1, R2, R3, R4, R5, R6 and Z are as defined in the specification, to compositions containing them, to processes for preparing them, and to their use in the treatment or prevention of conditio