458-03-7Relevant articles and documents
A product analytical study of the thermal and photolytic decomposition of some arenediazonium salts in solution
Canning, Peter S. J.,Maskill, Howard,McCrudden, Katharine,Sexton, Brian
, p. 789 - 800 (2007/10/03)
Products of thermal and photochemical reactions of eleven arenediazonium tetrafluoroborates in various solvents have been analyzed. All compounds in most solvents undergo unimolecular heterolysis to give singlet aryl cations which are captured by solvent. This mechanism is dominant for arenediazonium ions without electron-withdrawing substituents in all solvents, and the only reaction observed in water. Additionally, appreciable yields of fluoroarenes are obtained by fluoride abstraction by the aryl cation from fluorinated solvents and from tetrafluoroborate in fluorinated solvents. Yields from photochemical processes are very similar to those from thermal reactions indicating that the main reactions proceed through common or very similar intermediates. Aryl cations formed from ion-paired diazonium ions may react with the counterion, but fragmentation of dissociated diazonium ions leads only to solvent-derived product. Some arenediazonium ions in some solvents undergo an alternative radical reaction leading principally to hydrodediazoniation. It is proposed that this reaction involves initial rate-limiting electron transfer from ethanol to the arenediazonium ion followed rapidly by homolysis of the resultant aryldiazenyl radical. Within the same solvent cage, the aryl radical then either abstracts an α-hydrogen from the ethanol radical cation generated in the first step to give the reduction product and protonated acetaldehyde, or combines with it at the oxygen to give a protonated aryl ethyl ether.
Dediazoniation reactions of arenediazonium ions under solvolytic conditions: Fluoride anion abstraction from trifluoroethanol and α-hydrogen atom abstraction from ethanol
Canning, Peter S. J.,McCrudden, Katharine,Maskill, Howard,Sexton, Brian
, p. 1971 - 1972 (2007/10/03)
Arenediazonium salts decompose thermally and photochemically in trifluoroethanol to yield trifluoroethyl ethers and (in part by fluoride abstraction from the solvent) fluoroarenes; the less reactive compounds in trifluoroethanol decompose readily in ethanol to give arenes in a radical reaction involving abstraction of the α-hydrogen from the ethanol.
Phenethylthiazolylthiourea (PETT) compounds as a new class of HIV-1 reverse transcriptase inhibitors. 2. Synthesis and further structure-activity relationship studies of PETT analogs
Cantrell, Amanda S.,Engelhardt, Per,H?gberg, Marita,Jaskunas, S. Richard,Johansson, Nils Gunnar,Jordan, Christopher L.,Kangasmets?, Jussi,Kinnick, Michael D.,Lind, Peter,Morin Jr., John M.,Muesing,Noreén, Rolf,?berg, Bo,Pranc, Paul,Sahlberg, Christer,Ternansky, Robert J.,Vasileff, Robert T.,Vrang, Lotta,West, Sarah J.,Zhang, Hong
, p. 4261 - 4274 (2007/10/03)
Phenylethylthiazolylthiourea (PETT) derivatives have been identified as a new series of nonnucleoside inhibitors of HIV-1 RT. Structure-activity relationship studies of this class of compounds resulted in the identification of N-[2-(2-pyridyl)ethyl]-N'-[2-(5-bromopyridyl)]-thiourea hydrochloride (trovirdine; LY300046.HCl) as a highly potent anti-HIV-1 agent. Trovirdine is currently in phase one clinical trials for potential use in the treatment of AIDS. Extension of these structure-activity relationship studies to identify additional compounds in this series with improved properties is ongoing. A part of this work is described here. Replacement of the two aromatic moleties of the PETT compounds by various substituted or unsubstituted heteroaromatic rings was investigated. In addition, the effects of multiple substitution in the phenyl ring were also studied. The antiviral activities were determined on wild-type and constructed mutants of HIV-1 RT and on wild-type HIV-1 and mutant viruses derived thereof, Ile100 and Cys181, in cell culture assays. Some selected compounds were determined on double- mutant viruses, HIV-1 (Ile100/Asn103) and HIV-1 (Ile100/Cys181). A number of highly potent analogs were synthesized. These compounds displayed IC50's against wild-type RT between 0.6 and 5 nM. In cell culture, these agents inhibited wild-type HIV-1 with ED50's between I and 5 nM in MT-4 cells. In addition, these derivatives inhibited mutant HIV-1 RT (Ile 100) with IC50's between 20 and 50 nM and mutant HIV-1 RT (Cys 181) with IC50's between 4 and 10 nM, and in cell culture they inhibited mutant HIV-1 (Ile100) with ED50's between 9 and 100 nM and mutant HIV-1 (Cys181) with ED50's between 3 and 20 nM.
