1-(3,5-二氯-2,6-二羟基苯基)乙酮 | 87953-95-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-(3,5-二氯-2,6-二羟基苯基)乙酮
• 英文名称: 3,5-Dichloro-2,6-dihydroxyacetophenone
• 英文别名: 3,5-Dichlor-2,6-dihydroxy-acetophenon；1-(3,5-Dichloro-2,6-dihydroxyphenyl)ethanone
• CAS: 87953-95-5
• 化学式: C₈H₆Cl₂O₃
• 分子量: 221.04
• InChiKey: JPBMVUZFDSULAA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 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-(3,5-二氯-2,6-二羟基苯基)乙酮 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 5,7-Dichloro-2-(4-methoxy-benzyl)-3-methyl-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
• 作为产物：
  描述：

  2,6-二羟基苯乙酮 在 磺酰氯 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 1.5h， 生成 1-(3,5-二氯-2,6-二羟基苯基)乙酮
  参考文献：
  名称：

  Anti-viral compounds

  摘要：

  具有化学式（I）的化合物，其中取代基在此处定义。还提供了包含化学式（I）化合物的药物组合物，其中药物载体用于治疗由小核糖核酸病毒引起的疾病。还提供了一种治疗受小核糖核酸病毒引起的疾病的方法，包括在药物载体中使用化学式（I）的化合物。

  公开号：

  US06888033B1

文献信息

• 5,8-Quinoflavone. Synthesis and addition reactions
  作者：James H. Looker、James R. Edman、Charles A. Kingsbury

  DOI：10.1021/jo00178a013

  日期：1984.2
• 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：——
• Anti-viral compounds
  申请人：Arad Dorit

  公开号：US06888033B1

  公开（公告）日：2005-05-03

  A compound having the formula (I) wherein the substituents are defined herein. Also provided are pharmaceutical compositions including a compound of formula (I) in a pharmaceutical carrier, for treating a disease caused by a picornavirus. Also provided is a method of treating a subject with a disease caused by a picornavirus, including a compound of formula (I) in a pharmaceutical carrier.

  具有化学式（I）的化合物，其中取代基在此处定义。还提供了包含化学式（I）化合物的药物组合物，其中药物载体用于治疗由小核糖核酸病毒引起的疾病。还提供了一种治疗受小核糖核酸病毒引起的疾病的方法，包括在药物载体中使用化学式（I）的化合物。
• 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
  作者：Cheuk K. Lau、Patrice C. Belanger、John Scheigetz、Claude Dufresne、Haydn W. R. Williams、Alan L. Maycock、Yvan Guindon、Thomas Bach、Aimee L. Dallob

  DOI：10.1021/jm00126a008

  日期：1989.6

  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.