Stereochemistry | ABSOLUTE |
Molecular Formula | C21H27NO6 |
Molecular Weight | 389.4422 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 4 / 4 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CCNC1=CC(O)=C2C(=C1)\C=C\C[C@H](O)[C@H](O)C(=O)C=C[C@@H](C)[C@H](C)OC2=O
InChI
InChIKey=MWUFVYLAWAXDHQ-HMNLTAHHSA-N
InChI=1S/C21H27NO6/c1-4-22-15-10-14-6-5-7-16(23)20(26)17(24)9-8-12(2)13(3)28-21(27)19(14)18(25)11-15/h5-6,8-13,16,20,22-23,25-26H,4,7H2,1-3H3/b6-5+,9-8-/t12-,13+,16+,20+/m1/s1
E-6201 and discovered that the compound inhibits lipopolysaccharide-activated TNF-alpha reporter activity in THP-1-33 cells and selectively inhibits mitogen-activated protein kinase/extracellular signal-regulated kinase kinase (MEK)-1 and MEK kinase-1 in cell-free biochemical assays. In addition, E-6201 showed inhibitory activity in several other cell-based systems: 1) phosphorylation of c-jun N-terminal kinase and p38 MAPKs; 2) nuclear factor-kappaB and activated protein-1 activation in various cell types; 3) interleukin (IL)-2 production from human lymphocytes; 4) hyperproliferation of human keratinocytes; 5) IL-8 production from human keratinocytes; and 6) proinflammatory cytokine production from human peripheral blood mononuclear cells. Based on this data, E-6201 may be beneficial for treatment of inflammatory and hyperproliferative diseases such as psoriasis through its anti-inflammatory activities on immune cells and anti-hyperproliferative activities on keratinocytes. E-6201 exhibits anti-tumor efficacy against TNBC in vitro and anti-metastasis efficacy against triple-negative breast cancer in vivo.