4-氯-6-丙基-苯-1,3-二醇 | 6298-86-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-氯-6-丙基-苯-1,3-二醇
• 英文名称: 2-chloro-4-propyl-1,5-dihydroxybenzene
• 英文别名: 4-chloro-6-propyl-resorcinol；4-Chlor-6-propyl-resorcin；5-Chlor-2.4-dihydroxy-1-propyl-benzol；4-Chloro-6-propylbenzene-1,3-diol
• CAS: 6298-86-8
• 化学式: C₉H₁₁ClO₂
• 分子量: 186.638
• InChiKey: BVQLOFHRRBYYLL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 海关编码：
  2908199090

反应信息

• 作为反应物：
  描述：

  4-氯-6-丙基-苯-1,3-二醇 在 potassium carbonate 、 三氟乙酸 作用下， 以 丙酮 为溶剂， 反应 20.0h， 生成
  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：

  1-(3-氯-2,6-二羟基-5-丙基苯基)乙酮 在 氢溴酸 、 溶剂黄146 作用下， 反应 5.0h， 以49%的产率得到4-氯-6-丙基-苯-1,3-二醇
  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

• Benzofuran derivatives useful as inhibitors of mammalian leukotriene
  申请人：Merck Frosst Canada, Inc.

  公开号：US04863958A1

  公开（公告）日：1989-09-05

  Benzofuran derivatives, pharmaceutical compositions and methods of treatment are disclosed. These compounds are useful as inhibitors of mammalian leukotriene biosynthesis. As such, these compounds are useful therapeutic agents for treating allergic conditions, asthma, cardiovascular disorders, inflammation. The compounds ar also useful as analgesics and as cytoprotective agents.

  本文披露了苯并呋喃衍生物、药物组合物和治疗方法。这些化合物可用作哺乳动物白三烯生物合成的抑制剂。因此，这些化合物是治疗过敏症、哮喘、心血管疾病、炎症等疾病的有效治疗药物。这些化合物还可用作止痛剂和细胞保护剂。
• Benzofuran derivatives
  申请人：Merck Frosst Canada, Inc.

  公开号：US05087638A1

  公开（公告）日：1992-02-11

  Benzofuran derivatives, pharmaceutical compositions and methods of treatment are disclosed. These compounds are useful as inhibitors of mammalian leukotriene biosynthesis. As such, these compounds are useful therapeutic agents for treating allergic conditions, asthma, cardiovascular disorders, inflammation. The compounds are also useful as analgesics and as cytoprotective agents.

  本发明揭示了苯并呋喃衍生物、制药组合物和治疗方法。这些化合物可用作哺乳动物白三烯生物合成的抑制剂。因此，这些化合物是治疗过敏症、哮喘、心血管疾病、炎症的有用治疗剂。这些化合物也可用作镇痛剂和细胞保护剂。
• Chakravarti; Chakravarty, Journal of the Indian Chemical Society, 1939, vol. 16, p. 144,147
  作者：Chakravarti、Chakravarty

  DOI：——

  日期：——
• Tomita et al., Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1951, vol. 71, p. 73,76
  作者：Tomita et al.

  DOI：——

  日期：——
• N-butyl monochlor-resorcinol
  申请人：SQUIBB &

  公开号：US02151137A1

  公开（公告）日：1939-03-21