1. Academic Validation
  2. Structural requirements of (E)-6-benzylidene-4a-methyl-4,4a,5,6,7,8-hexahydronaphthalen-2(3H)-one derivatives as novel melanogenesis inhibitors

Structural requirements of (E)-6-benzylidene-4a-methyl-4,4a,5,6,7,8-hexahydronaphthalen-2(3H)-one derivatives as novel melanogenesis inhibitors

  • Bioorg Med Chem Lett. 2011 Apr 1;21(7):1922-5. doi: 10.1016/j.bmcl.2011.02.060.
Pillaiyar Thanigaimalai 1 Ki-Cheul Lee Vinay K Sharma Eeda Vekateswara Rao Eunmiri Roh Youngsoo Kim Sang-Hun Jung
Affiliations

Affiliation

  • 1 College of Pharmacy and Institute of Drug Research and Development, Chungnam National University, Daejeon 305-764, South Korea.
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.

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