- Synthesis and structure-activity relationships of phenylpropanoid amides of serotonin on tyrosinase inhibition
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In this manuscript, we synthesized a series of phenylpropanoid amide of serotonin 1-9, analyzed their structural importance for two biologic activities (antioxidant activity and tyrosinase inhibitory activity). While the serotonin moiety and the amide linkage of serotonin derivatives affect antioxidant activity strongly, the serotonin moiety, the amide linkage and the cinnamic acid moiety affect tyrosinase inhibitory activity. Among tested compounds, compound 4 which contains cathechol moiety exhibited the most antioxidant activity (EC50 = 19.4 ± 2.0 μM), and compound 6 exhibited significant tyrosinase inhibitory activity (IC50 = 5.4 ± 3.6 μM). Our data suggests that a useful clue for the design and development of new tyrosinase inhibitors.
- Takahashi, Toshiyuki,Miyazawa, Mitsuo
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- NOVEL AMIDE DERIVATIVE AND SKIN WHITENING AGENT
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Provision of a novel compound having a melanin production suppressive activity and the like. A compound represented by the following formula (I) wherein the symbols are as defined in the description, or a salt thereof, and a whitening agent containing the
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Page/Page column 14
(2012/02/14)
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- Synthesis and structure-activity relationships of serotonin derivatives effect on α-glucosidase inhibition
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The α-glucosidase inhibitory activities of serotonin derivatives were evaluated. Two serotonin derivatives, N-p-coumaroyl serotonin (2) and N-caffeoyl serotonin (4) exhibited most potent inhibition on α-glucosidase, whereas, cinnamic acid derivatives were
- Takahashi, Toshiyuki,Miyazawa, Mitsuo
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p. 1762 - 1770
(2012/11/14)
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- Serotonin derivatives as inhibitors of β-secretase (BACE 1)
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All serotonin derivatives described here (1-9) inhibited BACE 1 in a dose dependent manner. The 50% Inhibition Concentration (IC50) of N-cinnamoyl serotonin (1) was 86.7 ± 4.0 μM. The peptide conjugation of serotonin derivatives influenced the BACE 1 inhibitory activity. Among serotonin derivatives (1-8), introduction of substituents, such as hydroxyl and methoxy groups at the 4′-position decreased the inhibitory activity (N-p-coumaroyl serotonin (2), N-p-methoxy cinnamoyl serotonin (3)). With a hydroxylgroup at the 4′-position, and the meta-hydroxy function being substituted by a hydroxyl group or methoxy group (Ncaffeoyl serotonin (4), N-feruloyl serotonin (5)), inhibitory activity was weakened, (IC50 > 400 μM). BACE 1 inhibitory activity was effected by the substituents of the cinnamic acid moiety. This is the first report on Structure-Activity- Relationships (SAR) for the BACE 1-inhibiting activity of serotonin derivatives. These serotonin derivatives, which have anti-oxidative effects as well are expected to be useful in the study of the mechanisms of Alzheimer's disease.
- Takahashi,Miyazawa, Mitsuo
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p. 301 - 305
(2012/01/02)
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