Synthesis and structure-activity relationships of phenylpropanoid amides of serotonin on tyrosinase inhibition

Toshiyuki Takahashi; Mitsuo Miyazawa

doi:10.1016/j.bmcl.2011.02.028

Synthesis and structure-activity relationships of phenylpropanoid amides of serotonin on tyrosinase inhibition

Bioorg Med Chem Lett. 2011 Apr 1;21(7):1983-6. doi: 10.1016/j.bmcl.2011.02.028. Epub 2011 Feb 13.

Authors

Toshiyuki Takahashi¹, Mitsuo Miyazawa

Affiliation

¹ Department of Applied Chemistry, Faculty of Science and Engineering, Kinki University, 3-4-1 Kowakae, Higashiosaka-shi, Osaka 577-8502, Japan.

PMID: 21377874
DOI: 10.1016/j.bmcl.2011.02.028

Abstract

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 (EC(50) = 19.4 ± 2.0 μM), and compound 6 exhibited significant tyrosinase inhibitory activity (IC(50) = 5.4 ± 3.6 μM). Our data suggests that a useful clue for the design and development of new tyrosinase inhibitors.

MeSH terms

Amides / chemistry
Enzyme Inhibitors / pharmacology*
Monophenol Monooxygenase / antagonists & inhibitors*
Serotonin / chemical synthesis
Serotonin / chemistry*
Serotonin / pharmacology*
Structure-Activity Relationship

Substances

Amides
Enzyme Inhibitors
Serotonin
Monophenol Monooxygenase