- Synthesis of 3-[4-(dimethylamino)phenyl]alkyl-2-oxindole derivatives and their effects on neuronal cell death
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Novel 3-[4-(dimethylamino)phenyl]alkyl-2-oxindole analogs were synthesized by either of the following two pathways: (1) a sequence of Knoevenagel condensation of oxindole with (4-dimethylamino)cinnamaldehyde–hydrogenation, or (2) alkylation of oxindole dianion with [(4-dimethylamino)phenyl]alkyl halides. Subsequent alkylation at C-3 and/or N-1 of the oxindole skeleton by anion-based methods provided additional substituted derivatives for structure-activity relationship studies. Their effects on neuronal cell death induced by oxidative stress were evaluated by lactate dehydrogenase assay. Compounds with the alkyl chain length of 2–4 significantly suppressed the neuronal cell death. No significant change occurred in the activity by substitution with less-polar groups. The stereochemistry at C-3 of the oxindole core was also irrelevant for the neuroprotective effects of these compounds.
- Furuta, Kyoji,Kawai, Yu,Mizuno, Yosuke,Hattori, Yurika,Koyama, Hiroko,Hirata, Yoko
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supporting information
p. 4457 - 4461
(2017/09/12)
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- Rapid and Efficient Synthesis of 1H-Indol-2-yl-1H-quinolin-2-ones
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(Equation Presented) A concise and efficient synthesis of the novel indol-2-yl-1H-quinolin-2-one ring system found in the potent and selective KDR kinase inhibitors 1-3 is presented.
- Kuethe, Jeffrey T.,Wong, Audrey,Davies, Ian W.
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p. 3975 - 3978
(2007/10/03)
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- The serotonin 5-HT4 receptor. 2. Structure-activity studies of the indole carbazimidamide class of agonists.
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A number of substituted indole carbazimidamides were prepared and evaluated as 5-HT4 receptor agonists by using the isolated field-stimulated guinea pig ileum preparation. Their selectivity for the 5-HT4 receptor was established by examining their affinity for other 5-HT receptors using radioligand-binding techniques. Several selective and highly potent full as well as partial agonists emerged from this study. For example, 1b,d were found to be the most potent, full 5-HT4 receptor agonist described so far (EC50 = 0.5 and 0.8 nM, respectively), being 6 and 4 times more potent than serotonin itself. On the other hand, 5b and 1h appeared as partial 5-HT4 receptor agonists in the nonstimulated guinea pig ileum preparation with potencies, evaluated against serotonin action, respectively similar (5b, Ki = 12 nM) to and 300-fold higher (1h, Ki = 0.04 nM) than serotonin.
- Buchheit,Gamse,Giger,Hoyer,Klein,Kloeppner,Pfannkuche,Mattes
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p. 2331 - 2338
(2007/10/02)
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