240423-18-1Relevant articles and documents
Evaluation of Chemical Diversity of Biotinylated Chiral 1,3-Diamines as a Catalytic Moiety in Artificial Imine Reductase
Pellizzoni, Michela,Facchetti, Giorgio,Gandolfi, Raffaella,Fusè, Marco,Contini, Alessandro,Rimoldi, Isabella
, p. 1665 - 1670 (2016)
The possibility of obtaining an efficient artificial imine reductase was investigated by introducing a chiral cofactor into artificial metalloenzymes based on biotin-streptavidin technology. In particular, a chiral biotinylated 1,3-diamine ligand in coord
Synthesis of novel deuterium labelled derivatives of N-alkylated polyamines
H?kkinen, Merja R.,Kein?nen, Tuomo A.,Khomutov, Alex R.,Auriola, Seppo,Weisell, Janne,Alhonen, Leena,J?nne, Juhani,Veps?l?inen, Jouko
experimental part, p. 547 - 562 (2009/04/07)
Novel di-, tetra- and octadeuterated derivatives of mono-N-alkylated diaminopropanes, spermidines, spermines, symmetrically bis-N-alkylated spermines and unsymmetrically bis-N-alkylated spermines were synthesized. Deuterium labels were introduced into the RHNCH2CH2CN intermediate either by exchanging the protons next to the nitrile group under basic conditions with D2O-EtOD mixture or/and by reducing the nitrile group to a CD2-NH2 fragment with LiAlD4.
Synthesis of 3-substituted bicyclic imidazo[1,2-d][1,2,4]thiadiazoles and tricyclic benzo[4,5]imidazo[1,2-d][1,2,4]thiadiazoles
Leung-Toung, Regis,Tam, Tim F.,Zhao, Yanqing,Simpson, Craig D.,Li, Wanren,Desilets, Denis,Karimian, Khashayar
, p. 6230 - 6241 (2007/10/03)
A versatile synthetic route to potentially useful fused-ring [1,2,4]thiadiazole scaffolds (e.g., 7a and 10b) via exchange reactions of the precursor [1,2,4]thiadiazol-3-(2H)one derivatives (e.g., 6 and 9) with appropriately substituted nitriles (e.g., cyanogen bromide or p-toluenesulfonyl cyanide) under mild conditions is described. For example, the tricyclic 3-bromo [1,2,4]THD derivative (7a) underwent SNAr substitution with a variety of nucleophiles, which included amines, malonate esters and alcohols. Likewise, the bicyclic 3-p-tosyl [1,2,4]THD (10b) was employed as a template in reaction with diamines, and the resulting substituted diamines (e.g., 12a or 12e) were further selectively derivatized at the N1 and/or N2 positions in a linear fashion. The X-ray crystal structure of the 3-methyl bicyclic [1,2,4]THD (21) was obtained, and selective methylation at the N1 position via a protection-alkylation-deprotection protocol, as illustrated in Scheme 6, was confirmed. Alternatively, a short convergent synthesis of N1-functionalized derivatives from the reaction of 10b with appropriately substituted secondary amines was also developed. Hence, these synthetic strategies were advantageously exploited to provide access to a variety of diversely derivatized 3-substituted fused-ring [1,2,4]thiadiazole derivatives.
