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

Bioorganic and Medicinal Chemistry Letters

Volumn 21, Issue 7, 2011, Pages 1983-1986

  Takahashi, Toshiyuki ^a   Miyazawa, Mitsuo ^a  

^a KINKI UNIVERSITY   (Japan)

Author keywords

Phenylpropanoid amide; Serotonin; Structure activity relationships; Tyrosinase inhibitor

Indexed keywords

ENZYME INHIBITOR; KOJIC ACID; MONOPHENOL MONOOXYGENASE; PHENYLPROPANOID AMIDE DERIVATIVE; UNCLASSIFIED DRUG;

ANTIOXIDANT ACTIVITY; ARTICLE; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME ACTIVITY; IC 50; OXIDATION; SKIN PROTECTION; STRUCTURE ACTIVITY RELATION;

AMIDES; ENZYME INHIBITORS; MONOPHENOL MONOOXYGENASE; SEROTONIN; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 79952490199     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2011.02.028     Document Type: Article

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23. 50). The percentage of tyrosinase activity was calculated as follows: Tyrosinase activity (%) = [(C-D)/ (A-B)] x 100, where A is the absorbance at 492 nm without test sample, B is the absorbance at 492 nm without test sample and substrate, C is the absorbance at 492 nm with test sample, D is the absorbance at 492 nm with test sample, but without substrate.
24. The scavenging activity for the DPPH radical was performed according to the follow method. An amount of 500 μL of a 0.5 mM methanoic DPPH solution was mixed in a cuvette with 500 μL of cinnamic acid derivatives at different concentration levels. These cuvettes were shaken vigorously. The cuvettes were allowed to stand at 27 °C for 30 min, the absorbance was measured at 517 nm using a U-1500 spectrophotometer. The percentage of radical scavenging activity was calculated using the equation. Radical scavenging activity (%) = (Control OD-Sample OD/Control OD) x 100. All tests were performed in triplicate. BHT was used as a reference standard for the investigation of radical scavenging activity.
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27. 6) δ 165.1 (C-9′), 150.2 (C-5), 149.1 (C-4′), 146.7 (C-3′), 138.5 (C-7′), 130.8 (C-8), 127.9 (C-9), 127.8 (C-1′), 123.1 (C-2), 120.1 (C-6′), 119.7 (C-8′), 113.3 (C-5′), 112.1 (C-7), 111.6 (C-6), 111.3 (C-3), 110.8 (C-2′), 102.4 (C-4), 55.6 (4′-OMe), 39.4 (C-11), 25.4 (C-10).