Abstract
Chalcone type compound 1a ((E)-6′-benzylidene-4a′-methyl- 4′,4a′,7′,8′-tetrahydro-3′H-spiro[[1,3] dithiolane-2,2′-naphthalen]-5′(6′H)-one) was discovered as an potent inhibitor in melanogenesis. To define its structure-activity relationship, a series of analogs 1b-n, dithiolane truncated 2a-b and ring A removed 3a-e were prepared and evaluated. The electron donating substitution on the phenyl ring (ring C) rather than an electron withdrawing group and dithiolane motif of 1 are needed for the activity enhancement. The scaffold containing both rings A and B associated with α,β-unsaturated system connected to phenyl of 1 was essential for antimelanogenesis.
Original language | English (US) |
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Pages (from-to) | 1922-1925 |
Number of pages | 4 |
Journal | Bioorganic and Medicinal Chemistry Letters |
Volume | 21 |
Issue number | 7 |
DOIs | |
State | Published - Apr 1 2011 |
Bibliographical note
Funding Information:This work was supported by a Grant ( R01-2007-000-20099-0 ) and Priority Research Centers Program (2009-0093815) through the National Research Foundation of Korea (NRF) funded by the Ministry of Education, Science and Technology .
Keywords
- Chalcone
- Melanogenesis
- Melanoma B16 cells
- α-Melanocyte stimulating hormone