2243-54-1Relevant articles and documents
Phosphate selective alkylenebisurea receptors: Structure-binding relationship
Bla?ek, Vesna,Bregovi?, Nikola,Mlinari?-Majerski, Kata,Basari?, Nikola
, p. 3846 - 3857 (2011)
New host molecules for anions, adamantane, and alkyl urea derivatives substituted by naphthalene chromophores, were synthesized. Their binding with F-, Cl-, Br-, OAc-, HSO 4-, NO3-, and H2PO 4- was investigated by UV-vis, fluorescence and NMR spectroscopy. The anion binding ability of adamantyl bisurea derivatives was compared with the analogous host molecules, wherein the urea moieties are separated by flexible alkyl linkers of the same length, and adamantane monourea derivative. The host molecules show the highest selectivity toward F- and H2PO4-. The binding stoichiometry and the values of the association constants depend on the basicity of anions, availability of H-bonding sites, preorganization, and rigidity of the hosts, as well as solvent polarity and H-bonding availability. Rigid adamantane receptors, compared to flexible analogues show increased selectivity for H 2PO4-, whereas binding of OAc- is better with flexible receptors. The binding of OAc- and H 2PO4- was investigated by microcalorimetry. The stoichiometries and the stability constants of the corresponding complexes obtained by this method were in good agreement compared to those determined by UV-vis titrations. In both cases the enthalpic contribution to the overall complex stability was predominant.
N-methylimidazole-catalyzed synthesis of carbamates from hydroxamic acids via the lossen rearrangement
Yoganathan, Sabesan,Miller, Scott J.
, p. 602 - 605 (2013/04/11)
An efficient, one-pot, N-methylimidazole (NMI) accelerated synthesis of aromatic and aliphatic carbamates via the Lossen rearrangement is reported. NMI is a catalyst for the conversion of isocyanate intermediates to the carbamates. Moreover, the utility of arylsulfonyl chloride in combination with NMI minimizes the formation of often-observed hydroxamate-isocyanate dimers during the sequence. Under the present conditions, lowering of temperatures is also possible, enabling a mild protocol.
Highly selective c-Jun N-terminal kinase (JNK) 2 and 3 inhibitors with in vitro CNS-like pharmacokinetic properties prevent neurodegeneration
Probst, Gary D.,Bowers, Simeon,Sealy, Jennifer M.,Truong, Anh P.,Hom, Roy K.,Galemmo Jr., Robert A.,Konradi, Andrei W.,Sham, Hing L.,Quincy, David A.,Pan, Hu,Yao, Nanhua,Lin, May,Tóth, Gergley,Artis, Dean R.,Zmolek, Wes,Wong, Karina,Qin, Ann,Lorentzen, Colin,Nakamura, David F.,Quinn, Kevin P.,Sauer, John-Michael,Powell, Kyle,Ruslim, Lany,Wright, Sarah,Chereau, David,Ren, Zhao,Anderson, John P.,Bard, Frédérique,Yednock, Ted A.,Griswold-Prenner, Irene
scheme or table, p. 315 - 319 (2011/02/27)
In this Letter, we describe the discovery of selective JNK2 and JNK3 inhibitors, such as 10, that routinely exhibit >10-fold selectivity over JNK1 and >1000-fold selectivity over related MAPKs, p38α and ERK2. Substitution of the naphthalene ring affords an isoform selective JNK3 inhibitor, 30, with approximately 10-fold selectivity over both JNK1 and JNK2. A naphthalene ring penetrates deep into the selectivity pocket accounting for the differentiation amongst the kinases. Interestingly, the gatekeeper Met146 sulfide interacts with the naphthalene ring in a sulfur-π stacking interaction. Compound 38 ameliorates neurotoxicity induced by amyloid-β in human cortical neurons. Lastly, we demonstrate how to install propitious in vitro CNS-like properties into these selective inhibitors.
