6-(Biphenyl-4-yloxy)-hexanoic acid methyl ester | 914771-35-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 6-(Biphenyl-4-yloxy)-hexanoic acid methyl ester
• CAS: 914771-35-0
• 化学式: C₁₉H₂₂O₃
• 分子量: 298.382
• InChiKey: FVYGXSTXBOBMOO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.47
• 重原子数：
  22.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  维生素 C 、 6-(Biphenyl-4-yloxy)-hexanoic acid methyl ester 在 lipase acrylic resin from C_. antarctica (Novozyme 435(R)) 作用下， 以 2-甲基-2-丁醇 为溶剂， 60.0 ℃ 、20.0 kPa 条件下， 生成 [(2S)-2-[(2R)-3,4-dihydroxy-5-oxo-2H-furan-2-yl]-2-hydroxyethyl] 6-(4-phenylphenoxy)hexanoate
  参考文献：
  名称：

  Novel 6-O-acylated vitamin C derivatives as hyaluronidase inhibitors with selectivity for bacterial lyases

  摘要：

  Previously, we identified ascorbic acid 6-O-hexadecanoate as an up to 1500 times more potent inhibitor of bacterial and bovine hyaluronidases than the parent compound, vitamin C, and determined a crystal structure of hyaluronidase from Streptococcus pneumoniae in complex with the inhibitor. As the alkanoyl chain interacts with a hydrophobic patch of the enzyme we synthesized other 6-O-acylated vitamin C derivatives bearing various lipophilic residues and investigated the inhibition of Streptococcus agalactiae strain 4755 hyaluronidase (SagHyal(4755)) and of bovine testicular hyaluronidases (BTH) in a turbidimetric assay. All compounds showed selectivity for the bacterial enzyme. Whereas vitamin C 6-O-hexanoate only weakly inhibited SagHyal(4755), the inhibition of both enzymes increased with the length of the aliphatic chain. In the case of the 6-O-octadecanoate, IC50 values of 0.9 and 39 mu M for SagHyal(4755) and BTH, respectively, were determined. Partial replacement of the aliphatic chain with a phenyl, p-phenylene or p-biphenylyl group resulted in inhibitors with activity in the lower micromolar range, too. The title compounds are among the most potent inhibitors of both enzymes known to date. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.07.087
• 作为产物：
  描述：

  6-溴己酸甲酯 、 对羟基联苯 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 6-(Biphenyl-4-yloxy)-hexanoic acid methyl ester
  参考文献：
  名称：

  Trifluoromethyl ketones as inhibitors of histone deacetylase

  摘要：

  Trifluoromethyl ketones were found to be inhibitors of histone deacetylases (HDACs). Optimization of this series led to the identification of submicromolar inhibitors Such as 20 that demonstrated antiproliferative effects against the HT1080 and MDA 435 cell lines. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00754-0