4-hydroxy-7-chloro-2-(p-methoxybenzoyl)-3-methyl-5-propylbenzofuran | 120034-11-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-hydroxy-7-chloro-2-(p-methoxybenzoyl)-3-methyl-5-propylbenzofuran
• 英文别名: 2-(p-methoxybenzoyl)-3-methyl-4-hydroxy-5-propyl-7-chlorobenzofuran；(7-chloro-4-hydroxy-3-methyl-5-propyl-1-benzofuran-2-yl)-(4-methoxyphenyl)methanone
• CAS: 120034-11-9
• 化学式: C₂₀H₁₉ClO₄
• 分子量: 358.821
• InChiKey: HOQQGPAFCFKMMB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  59.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-hydroxy-7-chloro-2-(p-methoxybenzoyl)-3-methyl-5-propylbenzofuran 在 sodium cyanoborohydride 、 zinc(II) iodide 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 6.0h， 以75%的产率得到7-氯-2-[(4-甲氧基苯基)甲基]-3-甲基-5-丙基-1-苯并呋喃-4-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
• 作为产物：
  描述：

  7-氯-2-[(4-甲氧基苯基)甲基]-3-甲基-5-丙基-1-苯并呋喃-4-醇 在 aluminium chloride 作用下， 以 正己烷 为溶剂， 以0.30 gm (87%)的产率得到4-hydroxy-7-chloro-2-(p-methoxybenzoyl)-3-methyl-5-propylbenzofuran
  参考文献：
  名称：

  Benzofuran derivatives useful as inhibitors of mammalian leukotriene

  摘要：

  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。

  公开号：

  US04863958A1

文献信息

• 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。
• 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：——
• Benzofuran and benzothiophene derivatives, their use in inhibiting mammalian leukotriene biosynthesis, and pharmaceutical compositions containing these derivatives
  申请人：MERCK FROSST CANADA INC.

  公开号：EP0165810B1

  公开（公告）日：1989-08-23
• US4863958A
  申请人：——

  公开号：US4863958A

  公开（公告）日：1989-09-05
• US5087638A
  申请人：——

  公开号：US5087638A

  公开（公告）日：1992-02-11