1-(3-Chloro-2,6-dihydroxy-5-propyl-phenyl)-butan-1-one | 120058-71-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(3-Chloro-2,6-dihydroxy-5-propyl-phenyl)-butan-1-one
• 英文别名: 1-(3-Chloro-2,6-dihydroxy-5-propylphenyl)butan-1-one
• CAS: 120058-71-1
• 化学式: C₁₃H₁₇ClO₃
• 分子量: 256.729
• InChiKey: QBCKKQOIAVDAID-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(3-Chloro-2,6-dihydroxy-5-propyl-phenyl)-butan-1-one 在 sodium cyanoborohydride 、 zinc(II) iodide 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 6.0h， 生成 7-Chloro-2-(4-methoxy-benzyl)-3,5-dipropyl-benzofuran-4-ol
  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

文献信息

• LAU, CHEUK K.;BELANGER, PATRICE C.;SCHEIGETZ, JOHN;DUFRESNE, CLAUDE;WILLI+, J. MED. CHEM., 32,(1989) N, C. 1190-1197
  作者：LAU, CHEUK K.、BELANGER, PATRICE C.、SCHEIGETZ, JOHN、DUFRESNE, CLAUDE、WILLI+

  DOI：——

  日期：——