33334-11-1Relevant academic research and scientific papers
1-[(imidazolidin-2-yl)imino]indazole. Highly α2/I 1 selective agonist: Synthesis, X-ray structure, and biological activity
Sa?czewski, Franciszek,Kornicka, Anita,Rybczyńska, Apolonia,Hudson, Alan L.,Shu, Sean Miao,Gdaniec, Maria,Boblewski, Konrad,Lehmann, Artur
scheme or table, p. 3599 - 3608 (2009/04/06)
Novel benzazole derivatives bearing a (imidazolidin-2-yl)imino moiety at position 1 or 2 were synthesized by reacting 1-amino- or 2-aminobenzazoles with N,N′-bis(tert-butoxycarbonyl)imidazolidine-2-thione in the presence of HgCl2. Structures of
Synthesis and structure-activity relationships of N-propyl-N-(4- pyridinyl)-1H-indol-1-amine (besipirdine) and related analogs as potential therapeutic agents for Alzheimer's disease
Klein,Davis,Olsen,Wong,Huger,Smith,Petko,Cornfeldt,Wilker,Blitzer,Landau,Haroutunian,Martin,Effland
, p. 570 - 581 (2007/10/03)
A series of novel N-(4-pyridinyl)-1H-indol-1-amines and other heteroaryl analogs was synthesized and evaluated in tests to determine potential utility for the treatment of Alzheimer's disease. From these compounds, N-propyl-N- (4-pyridinyl)-1H-indol-1-amine (besipirdine, 4c) was selected for clinical development based on in-depth biological evaluation. In addition to cholinomimetic properties based initially on in vitro inhibition of [3H]quinuclidinyl benzilate binding, in vivo reversal of scopolamine- induced behavioral deficits, and subsequently on other results, 4c also displayed enhancement of adrenergic mechanisms as evidenced in vitro by inhibition of [3H]clonidine binding and synaptosomal biogenic amine uptake, and in vivo by reversal of tetrabenazine-induced ptosis. The synthesis, structure-activity relationships for this series, and the biological profile of 4c are reported.
1H- and 2H-Indazoles by Thermal and Photolytic Decomposition of o-Azidobenzoic Acid and o-Azidobenzaldehyde Derivatives
Ardakani, Manouchehr Azadi,Smalley, Robert K.,Smith, Richard H.
, p. 2501 - 2506 (2007/10/02)
Ethyl o-azidobenzimidate (6) and o-azidobenzamidine (7) on thermolysis yield 3-ethoxy- (9; X=OEt) and 3-amino-1H-indazole (9; X=NH2), respectively.The former product is also obtained on irradiation of the imidate in methanol-tetrahydrofuran solution. 2-Aryl- and 2-heteroaryl-3-chloro-2H-indazoles have been prepared by the action of hot thionyl chloride on o-azidoanilides.The trichloro-2H-indazoles obtained by the action of phosphorus pentachloride on o-azidobenzanilide (12) and by the action of thionyl chloride on N-(o-azidobenzoyl)-2-aminopyridine have been identified as the 3,5,7-trichloro derivatives.The reductive dehalogenation, nitration, and reactivity of the halogen towards nucleophiles, of 3-chloro-2-phenyl-2H-indazole (19) are reported.A new practicable synthesis of o-azidobenzaldehyde (31; X=O) is described.Thermolysis of its phenylhydrazone and semicarbazone derivatives yields 2H-indazoles.
