| RRC ID |
51588
|
| 著者 |
Ismail T, Shafi S, Srinivas J, Sarkar D, Qurishi Y, Khazir J, Alam MS, Kumar HM.
|
| タイトル |
Synthesis and tyrosinase inhibition activity of trans-stilbene derivatives.
|
| ジャーナル |
Bioorg Chem
|
| Abstract |
Synthesis of a focussed library of trans-stilbene compounds through Wittig and other base catalysed condensation reactions is presented. The synthesized stilbenes were screened for their inhibitory potential against murine tyrosinase activity to explore the structure activity relationship (SAR). Presence of electron withdrawing group (-CN) at the double bond and hydroxyl group or halogen atom especially at para-position on the aromatic rings was found to significantly elevate the inhibitory activity. Among all the compounds screened, compounds 2, 6, 8, 10, 11, 15 and 21 were found to exhibit appreciable inhibitory activity. Compound 21 ((E)-2,3-bis(4-Hydroxyphenyl)acryonitrile) was found to be the most active with an IC50 value of 5.06 μM which is less than half of the value 10.78 μM observed for resveratrol (common standard used in murine tyrosinase activity studies) under similar conditions. The results obtained from the present study reveal structural/functional group sensitivity for the tyrosinase inhibitory activity of stilbenoid moieties and are expected to be very helpful for the design and synthesis of novel, selective and effective tyrosinase inhibitors.
|
| 巻・号 |
64
|
| ページ |
97-102
|
| 公開日 |
2016-2-1
|
| DOI |
10.1016/j.bioorg.2016.01.001
|
| PII |
S0045-2068(16)30001-3
|
| PMID |
26773755
|
| MeSH |
Animals
Cell Line, Tumor
Enzyme Inhibitors / chemical synthesis
Enzyme Inhibitors / chemistry
Enzyme Inhibitors / pharmacology*
Mice
Monophenol Monooxygenase / antagonists & inhibitors*
Resveratrol
Stilbenes / chemical synthesis
Stilbenes / chemistry
Stilbenes / pharmacology*
Structure-Activity Relationship
|
| IF |
3.926
|
| 引用数 |
9
|
| リソース情報 |
| ヒト・動物細胞 |
B16 melanoma |
