52850-23-4Relevant articles and documents
Gas-phase pyrolytic reaction of 3-anilino-1-propanol derivatives: kinetic and mechanistic study
Ibrahim,Al-Awadi,Ibrahim,Patel,Al-Awadi
, p. 4768 - 4772 (2007/10/03)
3-Anilino-1-propanol derivatives 4a-c, 5a-c, 6a-c containing primary, secondary, and tertiary alcohols and PhNH, PhNMe, and (Ph)2N were prepared and subjected to gas-phase pyrolysis in a static reaction system. The pyrolytic reactions were homogeneous and followed a first-order rate equation. Reactions took place by retro-ene process, with the exception of compounds 5a and 5b. Analysis of the pyrolysate showed the products to be N-substituted aniline and carbonyl compounds. The kinetic results and product analysis of each of the nine investigated 3-amino alcohols are rationalized in terms of a plausible transition state for the elimination pathway.
Facile N-Arylation of Amines and Sulfonamides
Liu, Zhijian,Larock, Richard C.
, p. 4673 - 4675 (2007/10/03)
(Matrix presented) A facile, transition-metal-free N-arylation procedure for amines and sulfonamides has been developed, which affords good to excellent yields of arylated products under very mild reaction conditions. A methoxy-substituted aryl triflate affords N-arylated products in high yields with excellent regioselectivity. This chemistry tolerates a variety of functional groups.
Synthesis of novel GABA uptake inhibitors. 4. Bioisosteric transformation and successive optimization of known GABA uptake inhibitors leading to a series of potent anticonvulsant drug candidates
Andersen, Knud Erik,S?rensen, Jan L.,Huusfeldt, Per O.,Knutsen, Lars J. S.,Lau, Jesper,Lundt, Behrend F.,Petersen, Hans,Suzdak, Peter D.,Swedberg, Michael D. B.
, p. 4281 - 4291 (2007/10/03)
By bioisosteric transformations and successive optimization of known GABA uptake inhibitors, several series of novel GABA uptake inhibitors have been prepared by different synthetic approaches. These compounds are derivatives of nipecotic acid and guvacine, substituted at the nitrogen of these amino acids by various lipophilic moieties such as diarylaminoalkoxyalkyl or diarylalkoxyalkyl. The in vitro values for inhibition of [3H]GABA uptake in rat synaptosomes was determined for each compound, and it was found that the most potent compound from this series, (R)-1-(2-(3,3-diphenyl-1-propyloxy)ethyl)-3-piperidinecarboxylic acid hydrochloride (29), is so far the most potent parent compound inhibiting GABA uptake into synaptosomes. Structure-activity results confirm our earlier observations, that an electronegative center in the chain connecting the amino acid and diaryl moiety is very critical in order to obtain high in vitro potency. Several of the novel compounds were also evaluated for their ability in vivo to inhibit clonic seizures induced by a 15 mg/kg (ip) dose of methyl 6,7-dimethoxy-4-ethyl-β-carboline-3-carboxylate (DMCM). Some of the compounds tested show a high in vivo potency comparable with that of the recently launched anticonvulsant product 6 ((R)-1-(4,4-bis(3-methyl-2- thienyl)-3-butenyl)-3-piperidinecarboxylic acid).
