Methyl 3-(2-(4-(adamantan-1-yl)phenoxy)acetamido)-4-hydroxybenzoate 3-(2-(4-(金刚烷-1-基)苯氧基)乙酰胺基)-4-羟基苯甲酸甲酯
CAS 934593-90-5 MFCD034593905
化学结构图
SMILES: COC(=O)c1ccc(O)c(NC(=O)COc2ccc(C34CC5CC(CC(C5)C3)C4)cc2)c1
化学属性
| Mol. Formula | C26H29NO5 |
|---|---|
| Mol. Weight | 435.51216 |
| Appearance | white solid powder |
| Solubility | Soluble in DMSO, not in water |
别名和识别编码
| Chemical Name | Methyl 3-(2-(4-(adamantan-1-yl)phenoxy)acetamido)-4-hydroxybenzoate |
|---|---|
| Chemical Name Translation | 3-(2-(4-(金刚烷-1-基)苯氧基)乙酰胺基)-4-羟基苯甲酸甲酯 |
| Reaxys-RN | 11008797 |
| MDL Number | MFCD09907563 |
| Formula | C26H29NO5 |
| Synonym | CAY10585; CAY-10585; CAY 10585; LW6; LW-6; LW 6 |
| IUPAC Name | methyl 3-(2-(4-(adamantan-1-yl)phenoxy)acetamido)-4-hydroxybenzoate |
| InChIKey | BJRPPNOJYFZSLY-UHFFFAOYSA-N |
| InChI | InChI=1S/C26H29NO5/c1-31-25(30)19-2-7-23(28)22(11-19)27-24(29)15-32-21-5-3-20(4-6-21)26-12-16-8-17(13-26)10-18(9-16)14-26/h2-7,11,16-18,28H,8-10,12-15H2,1H3,(H,27,29) |
| Canonical SMILES | O=C(OC)C1=CC=C(O)C(NC(COC2=CC=C(C34CC5CC(C4)CC(C5)C3)C=C2)=O)=C1 |
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- CAY10585, also known as LW6, was first identified and reported by a group scientists from Korea. LW8 was found to inhibits the accumulation of HIF-1alpha. LW6 decreased HIF-1alpha protein expression without affecting HIF-1beta expression. It was further found that LW8 promoted the degradation of wild type HIF-1alpha, but not of a DM-HIF-1alpha with modifications of P402A and P564A, at hydroxylation sites in the oxygen-dependent degradation domain (ODDD). LW6 did not affect the activity of prolyl hydroxylase (PHD), but induced the expression of von Hippel-Lindau (VHL), which interacts with prolyl-hydroxylated HIF-1alpha for proteasomal degradation. In the presence of LW8, knockdown of VHL did not abolish HIF-1alpha protein accumulation, indicating that LW8 degraded HIF-1alpha via regulation of VHL expression. In mice carrying xenografts of human colon cancer HCT116 cells, LW8 demonstrated strong anti-tumor efficacy in vivo and caused a decrease in HIF-1alpha expression in frozen-tissue
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