61640-27-5Relevant articles and documents
New bis(mercaptoimidazolyl)(pyrazolyl)borate ligands and their zinc complex chemistry
Shu, Mouhai,Walz, Rainer,Wu, Biao,Seebacher, Jan,Vahrenkamp, Heinrich
, p. 2502 - 2511 (2007/10/03)
Nine new tripodal NS2 ligands of the bis(mercaptoimidazolyl)(pyrazolyl)borate type with varying 3-R-mercaptoimidazolyl moieties were prepared as their potassium salts. Treatment with zinc salts yielded the complex types L·Zn-Cl, L·Zn-I, L·Zn-ONO2, L·Zn-OClO3 and [L·Zn(imidazole)]ClO4. Attempts at the formation of L·Zn-OH or cationic L·Zn complexes resulted in dismutation and formation of ZnL2 complexes. Hydrolytic destruction yielded one [OZn4(thiooimidazolate)6] complex. The ZnS2NO coordination which is present in the enzyme-substrate complex of alcohol dehydrogenase could be successfully modelled by an [L·Zn(C2H5OH)]+ complex. The L·Zn-X complexes showed very low catalytic activity in the dehydrogenation of 2-propanol or the hydrogenation of p-nitrobenzaldehyde. The new compounds were identified by a total of 12 structure determinations. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.
Quaternary salts of 2-[(hydroxyimino)methyl]imidazole. 3. Synthesis and evaluation of (alkenyloxy)-, (alkynyloxy)-, and (aralkyloxy)methyl quaternarized 2[(hydroxyimino)methyl]-1-alkylimidazolium halides as reactivators and therapy for soman intoxication
Bedford,Harris III,Howd,Goff,Koolpe,Petesch,Koplovitz,Sultan,Musallam
, p. 504 - 516 (2007/10/02)
A series of structurally related monosubstituted 1-[(alkenyloxy)methyl]-, 1-[(alkynyloxy)methyl]-, and 1-[(aralkyloxy)methyl]-2-[(hydroxyimino)methyl]-3-methylimidazolium halides were prepared and evaluated. All new compounds were characterized with respect to (hydroxyimino)methyl acid dissocation constant, nucleophilicity, and octanol-buffer partition coefficient. The alkynyloxy-substituted compounds were also evaluated in vitro with respect to reversible inhibition of human erythrocyte (RBC) acetylcholinesterase (AChE) and kinetics of reactivation of human AChE inhibited by ethyl p-nitrophenyl methylphosphonate (EPMP). In vivo evaluation in mice revealed that coadministration of alkynyloxy-substituted imidazolium compounds with atropine sulfate provided significant protection against a 2 x LD50 challenge of GD. For the alkynyloxy-substituted imidazolium drugs there is a direct relationship between in vitro and in vivo activity: the most potent in vivo compounds against GD proved to be potent in vitro reactivators against EPMP-inhibited human AChE. These results differ from the observations made on the sterically hindered imidazolium compounds (see previous article) and suggest that several antidotal mechanisms of protective action may be applicable for the imidazolium aldoxime family of therapeutics. The ability of the alkynyloxy substituents to provide life-saving protection against GD intoxication was not transferable to the pyridinium or triazolium heteroaromatic ring systems.
