59397-23-8Relevant articles and documents
Azetidine derivatives and synthesis method thereof
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, (2019/03/26)
The invention belongs to the field of chemical synthesis, and discloses an azetidine derivative and a synthesis method thereof. The structural formula of the target product azetidine derivatives is asshown in formulae (I), (II), (III), (IV) and (V). The compounds of the formulae are compounds containing an azetidine skeleton, and a nitrogen atom in the skeleton is protected by 2-picolinic acid. The target product azetidine derivatives can be: azetidinyl amide derivatives, azabicyclo[x.1.1] amide derivatives (x=3, 4, 5, 6, 7, 8, 9), azabicyclo[4.1.1] amide derivatives having a substituent at the ring, azabicyclo[4.2.0] amide derivatives and azetidine derivatives containing spirocyclic quaternary carbon. The azetidine derivatives of the present invention have certain protective effect on hydrogen peroxide-induced oxidative stress damage of HC cells.
Syntheses and N-methyl-D-aspartate receptor antagonist pharmacology of fluorinated arylcycloheptylamines
Sun, Shengguo,Wallach, Jason,Adejare, Adeboye
, p. 843 - 852 (2015/04/14)
Selective uncompetitive antagonists of the phencyclidine (PCP) binding site of the N-methyl-D-aspartate receptor (NMDAR) are known to have therapeutic potential as anticonvulsants and neuroprotective agents. Several fluorinated molecules with each containing a cycloheptane ring were designed to probe the PCP pharmacophore and test the influence of fluorine substitution on NMDAR binding and in vivo efficacy. Syntheses and analyses of six novel compounds, 1-(4-fluorophenyl)cycloheptanamine (3), 1-(1-(4-fluorophenyl)cycloheptyl)piperidine (4), 1-(1-(4-fluorophenyl)cycloheptyl) pyrrolidine (5), 1-(3-fluorophenyl)cycloheptanamine (6), 1-(1-(3-fluorophenyl)cycloheptyl)piperidine (7), 1-(1-(3-fluorophenyl)cycloheptyl)pyrrolidine (8) and several related reference arylcyloalkylamines are described. Receptor binding was performed at the PCP site of NMDAR for each compound using [3H]-(+)-MK-801 displacement. Unexpectedly, the 3-fluoro-primary amine 6 had the greatest affinity of the series and these binding results support a different structure activity relationship (SAR) profile for arylcycloheptylamines when compared to arylcyclohexylamines like PCP. Five of the novel compounds have affinity (Ki) in the hundred nM (10-7) range. In addition, compounds 3, 5, 6, 7 and 8 were evaluated and found to exhibit neuroprotective effects from NMDA induced toxicity in vitro and compounds 6, 7 and 8 exhibited anticonvulsant activities in rats. An ED50 of 13.84 mg/kg was found for compound 6 in rat maximal electroshock (MES) test with a protective index (PI) of 3.66 against ataxia. These results support further investigation of the arylcycloheptylamine class.
2-Phenyl-2-adamantanamine hydrochloride
Kalir, Asher,Balderman, David
, p. 104 - 104 (2017/05/26)
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