5999-20-2Relevant articles and documents
Novel water-soluble sedative-hypnotic agents: Isoindolin-1-one derivatives
Kanamitsu, Norimasa,Osaki, Takashi,Itsuji, Yutaka,Yoshimura, Masakazu,Tsujimoto, Hisashi,Soga, Manabu
, p. 1682 - 1688 (2008/12/21)
We developed new intravenous sedative-hypnotic compounds with the isoindolin-1-one skeleton focusing on the water-soluble property and in vivo safety. We synthesized approximately 170 derivatives and evaluated their hypnotic effects by intravenous administration of the compounds to mice. A series of the 2-phenyl-3-[2-(4-methyl-1-piperazinyl)-2-oxoethyl]isoindolin-1-one analogs, 3(-), 5(-), 27(-), and 47(-) [JM-1232(-)], showed potent sedative-hypnotic activity with good water solubility and a wide safety margin. The hypnotic doses (HD50s) of these 4 compounds when administered to mice were 2.35, 1.90, 2.17, and 3.12 mg/kg, respectively, and the lethal doses (LD50s) were 88.67, 64.69, >120, and >120 mg/kg, respectively. The therapeutic indexes (LD50/HD50) were 37.73, 34.05, >55.30, and >38.46, respectively. Among these compound, 47(-) [JM-1232(-)] is being considered as the most potential candidate for clinical trials in humans.
Hydrogen-bond symmetry in zwitterionic phthalate anions: Symmetry breaking by solvation
Perrin, Charles L.,Lau, Jonathan S.
, p. 11820 - 11824 (2007/10/03)
The cationic nitrogen of zwitterion 1 is located symmetrically with respect to its intramolecular OHO hydrogen bond. Incorporation of one 18O allows investigation of the H-bond symmetry by the NMR method of isotopic perturbation. In both CDsub
Studies on the Chemistry of Isoindoles and Isoindolenines, XXVIII. - 3-Alkoxy-1H-isoindoles, Syntheses and Properties
Hennige, Hans,Kreher, Richard P.,Konrad, Michael,Jelitto, Frank
, p. 243 - 252 (2007/10/02)
3-Alkoxy-1H-isoindoles 1 bearing substituents at the carboxylic moiety have been synthesized from substituted 2,3-dihydro-1H-isoindol-1-ones 4 by regiospecific O-alkylation to 5 with trialkyloxonium tetrafluoroborates or methyl trifluoroborates or methyl trifluoromethanesulfonate and subsequent NH deprotonation.According to the spectroscopic properties the semicyclic alkyl imidates 1 exist exclusively in the benzoid 1H structure; the tautomeric o-quinonoid 2H structure 2 cannot be detected by spectroscopic means.
