5219-07-8Relevant articles and documents
Copper-catalysed: N -arylation of 5-aminopyrazoles: A simple route to pyrazolo[3,4- b] indoles
Chatterjee, Arpita,Murmu, Chudamani,Peruncheralathan, S.
supporting information, p. 6571 - 6581 (2020/11/07)
A copper-catalysed intramolecular N-arylation of 5-aminopyrazoles is demonstrated for the first time. Highly substituted pyrazolo[3,4-b]indoles are synthesized. In particular, the indole core is decorated with halogens and alkyl and methoxy groups. Furthermore, a selective N-arylation of unsymmetrical diaryl bromide containing pyrazoles is exemplified, resulting in valuable pyrazolo[1,5-a]benzimidazoles. This journal is
Pyrimethamine Derivatives: Insight into Binding Mechanism and Improved Enhancement of Mutant β- N -acetylhexosaminidase Activity
Tropak, Michael B.,Zhang, Jianmin,Yonekawa, Sayuri,Rigat, Brigitte A.,Aulakh, Virender S.,Smith, Matthew R.,Hwang, Hee-Jong,Ciufolini, Marco A.,Mahuran, Don J.
, p. 4483 - 4493 (2015/06/23)
In order to identify structural features of pyrimethamine (5-(4-chlorophenyl)-6-ethylpyrimidine-2,4-diamine) that contribute to its inhibitory activity (IC50 value) and chaperoning efficacy toward β-N-acetylhexosaminidase, derivatives of the compound were synthesized that differ at the positions bearing the amino, ethyl, and chloro groups. Whereas the amino groups proved to be critical to its inhibitory activity, a variety of substitutions at the chloro position only increased its IC50 by 2-3-fold. Replacing the ethyl group at the 6-position with butyl or methyl groups increased IC50 more than 10-fold. Surprisingly, despite its higher IC50, a derivative lacking the chlorine atom in the para-position was found to enhance enzyme activity in live patient cells a further 25% at concentrations >100 μM, while showing less toxicity. These findings demonstrate the importance of the phenyl group in modulating the chaperoning efficacy and toxicity profile of the derivatives.
Synthesis of N-substituted indole derivatives via PIFA-mediated intramolecular cyclization
Du, Yunfei,Liu, Renhe,Linn, Gregory,Zhao, Kang
, p. 5919 - 5922 (2007/10/03)
(Chemical Equation Presented) A variety of N-arylated and N-alkylated indole derivatives were synthesized by way of a phenyliodine bis(trifluoroacetate) (PIFA)-mediated intramolecular cyclization. This novel method allows for the construction of an indole skeleton by joining the N-atom on the side chain to the benzene ring at the last synthetic step. Other novel pyrrole-fused aromatic compounds can also be achieved by this method.