3-[7-Chloro-2-(4-methoxy-benzyl)-3-methyl-4-(1-methyl-1-trimethylsilanyl-ethoxy)-benzofuran-5-yl]-propionic acid | 120034-25-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: 3-[7-Chloro-2-(4-methoxy-benzyl)-3-methyl-4-(1-methyl-1-trimethylsilanyl-ethoxy)-benzofuran-5-yl]-propionic acid
• CAS: 120034-25-5
• 化学式: C₂₆H₃₃ClO₅Si
• 分子量: 489.084
• InChiKey: BFXARGOGOQCBKZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.05
• 重原子数：
  33.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  68.9
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3-[7-Chloro-2-(4-methoxy-benzyl)-3-methyl-4-(1-methyl-1-trimethylsilanyl-ethoxy)-benzofuran-5-yl]-propionic acid 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 以143 mg的产率得到4-hydroxy-5-(carboxyethyl)-7-chloro-2-<(4'-methoxyphenyl)methyl>-3-methylbenzofuran
  参考文献：
  名称：

  Synthesis and structure-activity relationships of a novel class of 5-lipoxygenase inhibitors. 2-(Phenylmethyl)-4-hydroxy-3,5-dialkylbenzofurans: the development of L-656,224

  摘要：

  The synthesis of a series of 2-(phenylmethyl)-4-hydroxy-3,5-dialkylbenzofurans and their inhibitory effects against leukotriene biosynthesis and 5-lipoxygenase activity in vitro are described. Many compounds in this series were found to be potent inhibitors of LTB4 production by human polymorphonuclear leukocytes with IC50 values ranging from 7 to 100 nM. Structure-activity relationships of the series are presented. Within this series, 2-[(4'-methoxyphenyl)methyl]-4-hydroxy-3-methyl-5-propyl-7-chlorobenz ofuran (L-656,224) showed extremely potent activity, inhibiting leukotriene biosynthesis in intact human leukocytes (IC50 = 11 nM), as well as the 5-lipoxygenase reaction catalyzed by cell-free preparations from rat leukocytes (IC50 = 36 nM), human leukocytes (IC50 = 0.4 microM), and the purified enzyme from porcine leukocytes (IC50 = 0.4 microM). The compound also shows oral activity in a number of animal models in vivo.

  DOI：

  10.1021/jm00126a008
• 作为产物：
  描述：

  5-allyl-4-hydroxy-7-chloro-2-<(4'-methoxyphenyl)methyl>-3-methylbenzofuran 在 4-二甲氨基吡啶 、 jones reagent 、 十二/十四烷基二甲基氧化胺 、 硼烷 、 三乙胺 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 25.0h， 生成 3-[7-Chloro-2-(4-methoxy-benzyl)-3-methyl-4-(1-methyl-1-trimethylsilanyl-ethoxy)-benzofuran-5-yl]-propionic acid
  参考文献：
  名称：

  Synthesis and structure-activity relationships of a novel class of 5-lipoxygenase inhibitors. 2-(Phenylmethyl)-4-hydroxy-3,5-dialkylbenzofurans: the development of L-656,224

  摘要：

  The synthesis of a series of 2-(phenylmethyl)-4-hydroxy-3,5-dialkylbenzofurans and their inhibitory effects against leukotriene biosynthesis and 5-lipoxygenase activity in vitro are described. Many compounds in this series were found to be potent inhibitors of LTB4 production by human polymorphonuclear leukocytes with IC50 values ranging from 7 to 100 nM. Structure-activity relationships of the series are presented. Within this series, 2-[(4'-methoxyphenyl)methyl]-4-hydroxy-3-methyl-5-propyl-7-chlorobenz ofuran (L-656,224) showed extremely potent activity, inhibiting leukotriene biosynthesis in intact human leukocytes (IC50 = 11 nM), as well as the 5-lipoxygenase reaction catalyzed by cell-free preparations from rat leukocytes (IC50 = 36 nM), human leukocytes (IC50 = 0.4 microM), and the purified enzyme from porcine leukocytes (IC50 = 0.4 microM). The compound also shows oral activity in a number of animal models in vivo.

  DOI：

  10.1021/jm00126a008