1.
Bioorg Med Chem Lett
; 21(7): 1922-5, 2011 Apr 01.
Artigo
em Inglês
| MEDLINE
| ID: mdl-21388810
RESUMO
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,ß-unsaturated system connected to phenyl of 1 was essential for antimelanogenesis.