7-<<3-(4-methoxytetrahydro-2H-pyran-4-yl)phenyl>methoxy>-4-phenylnaphtho<2,3-c>furan-1(3H)-one | 144819-26-1

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 芳基萘木脂素
• 英文名称: 7-<<3-(4-methoxytetrahydro-2H-pyran-4-yl)phenyl>methoxy>-4-phenylnaphtho<2,3-c>furan-1(3H)-one
• 英文别名: 6-[[3-(4-methoxyoxan-4-yl)phenyl]methoxy]-9-phenyl-1H-benzo[f][2]benzofuran-3-one
• CAS: 144819-26-1
• 化学式: C₃₁H₂₈O₅
• 分子量: 480.56
• InChiKey: VYQIKMSBOJBSHY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  36
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  7-<<3-(4-methoxytetrahydro-2H-pyran-4-yl)phenyl>methoxy>-4-phenylnaphtho<2,3-c>furan-1(3H)-one 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 21.0h， 以98%的产率得到Sodium; 3-hydroxymethyl-7-[3-(4-methoxy-tetrahydro-pyran-4-yl)-benzyloxy]-4-phenyl-naphthalene-2-carboxylate
  参考文献：
  名称：

  Naphthalenic Lignan Lactones as Selective, Nonredox 5-Lipoxygenase Inhibitors. Synthesis and Biological Activity of (Methoxyalkyl)thiazole and Methoxytetrahydropyran Hybrids

  摘要：

  Combinations of structural elements found in (methoxyalkyl)thiazole 1a and methoxytetrahydropyran 2a with a naphthalenic lignan lactone produce the potent 5-lipoxygenase (5-LO) inhibitors 3 and 4. While the nature of link Y-Z has a major effect on the in vitro activity of compounds 1 and 2, inhibitors 3 and 4 retain their potencies with either an oxymethylene (Y = O, Z = CH2) or a methyleneoxy (Y = CH2, Z = O) link. Compound 4b inhibits the oxidation of arachidonic acid to 5-hydroperoxyeicosatetraenoic acid by 5-LO (IC50 = 14 nM) and the formation of leukotriene Bq in human polymorphonuclear leukocytes (IC50 = 1.5 nM) as well as in human whole blood (IC50 = 50 nM). Compound 4b is a selective 5-LO inhibitor showing no significant inhibition of human 15-lipoxygenase or porcine 12-lipoxygenase or binding to human 5-lipoxygenase-activating protein up to 10 mu M and inhibits leukotriene biosynthesis by a direct, nonredox interaction with 5-LO. Compound 15, the open form of lactone 4b, is well absorbed in the rat and is transformed into the active species 4b. In addition, 15 is orally active in the rat pleurisy model (ED(50) = 0.6 mg/kg) and in the functional model of antigen-induced bronchoconstriction in allergic squirrel monkeys (95% inhibition at 0.3 mg/kg).

  DOI：

  10.1021/jm00030a010
• 作为产物：
  描述：

  3-(4-methoxytetrahydro-2H-pyran-4-yl)toluene 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 potassium carbonate 作用下， 以 四氯化碳 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.5h， 生成 7-<<3-(4-methoxytetrahydro-2H-pyran-4-yl)phenyl>methoxy>-4-phenylnaphtho<2,3-c>furan-1(3H)-one
  参考文献：
  名称：

  Naphthalenic Lignan Lactones as Selective, Nonredox 5-Lipoxygenase Inhibitors. Synthesis and Biological Activity of (Methoxyalkyl)thiazole and Methoxytetrahydropyran Hybrids

  摘要：

  Combinations of structural elements found in (methoxyalkyl)thiazole 1a and methoxytetrahydropyran 2a with a naphthalenic lignan lactone produce the potent 5-lipoxygenase (5-LO) inhibitors 3 and 4. While the nature of link Y-Z has a major effect on the in vitro activity of compounds 1 and 2, inhibitors 3 and 4 retain their potencies with either an oxymethylene (Y = O, Z = CH2) or a methyleneoxy (Y = CH2, Z = O) link. Compound 4b inhibits the oxidation of arachidonic acid to 5-hydroperoxyeicosatetraenoic acid by 5-LO (IC50 = 14 nM) and the formation of leukotriene Bq in human polymorphonuclear leukocytes (IC50 = 1.5 nM) as well as in human whole blood (IC50 = 50 nM). Compound 4b is a selective 5-LO inhibitor showing no significant inhibition of human 15-lipoxygenase or porcine 12-lipoxygenase or binding to human 5-lipoxygenase-activating protein up to 10 mu M and inhibits leukotriene biosynthesis by a direct, nonredox interaction with 5-LO. Compound 15, the open form of lactone 4b, is well absorbed in the rat and is transformed into the active species 4b. In addition, 15 is orally active in the rat pleurisy model (ED(50) = 0.6 mg/kg) and in the functional model of antigen-induced bronchoconstriction in allergic squirrel monkeys (95% inhibition at 0.3 mg/kg).

  DOI：

  10.1021/jm00030a010

文献信息

• Drug delivery from rapid gelling polymer composition
  申请人：ANGIOTECH INTERNATIONAL AG

  公开号：EP2181704A2

  公开（公告）日：2010-05-05

  Compositions are disclosed that afford drug delivery from two-part polymer compositions that rapidly form covalent linkages when mixed together. Such compositions are particularly well suited for use in a variety of tissue related applications when rapid adhesion to the tissue and gel formation is desired along with drug delivery. For example, the compositions are useful as tissue sealants, in promoting hemostasis, in effecting tissue adhesion, in providing tissue augmentation, and in prevention of surgical adhesions.

  本发明公开了一些组合物，这些组合物由两部分聚合物组成，在混合在一起时可迅速形成共价连接，从而实现药物输送。当需要快速粘附组织和形成凝胶并同时给药时，这种组合物特别适合用于各种与组织相关的应用。例如，这种组合物可用作组织密封剂、促进止血、实现组织粘合、提供组织增量以及防止手术粘连。
• Anastomotic connector devices
  申请人：Angiotech International AG

  公开号：US20040260318A1

  公开（公告）日：2004-12-23

  Anastomotic connector devices are provided which release a therapeutic agent. The therapeutic agent may be an anti-scarring agent that inhibits stenosis caused by the presence of the anastomotic connector device.

  所提供的吻合口连接器装置可释放一种治疗剂。治疗剂可以是一种抗疤痕剂，可抑制因吻合连接装置的存在而造成的狭窄。
• Polymer compositions and methods for their use
  申请人：Hunter L. William

  公开号：US20050178395A1

  公开（公告）日：2005-08-18

  Compositions comprising anti-fibrotic agent(s) and/or polymeric compositions can be used in various medical applications including the prevention of surgical adhesions, treatment of inflammatory arthritis, treatment of scars and keloids, the treatment of vascular disease, and the prevention of cartilage loss.

  包含抗纤维化剂和/或聚合物的组合物可用于各种医疗应用，包括预防手术粘连、治疗炎症性关节炎、治疗疤痕和瘢痕疙瘩、治疗血管疾病以及预防软骨流失。
• Implantable sensors and implantable pumps and anti-scarring agents
  申请人：Hunter L. William

  公开号：US20050181005A1

  公开（公告）日：2005-08-18

  Pumps and sensors for contact with tissue are used in combination with an anti-scarring agent (e.g., a cell cycle inhibitor) in order to inhibit scarring that may otherwise occur when the pumps and sensors are implanted within an animal.

  用于与组织接触的泵和传感器与抗疤痕剂（如细胞周期抑制剂）结合使用，以抑制在动物体内植入泵和传感器时可能出现的疤痕。
• Electrical devices and anti-scarring agents
  申请人：Hunter L. William

  公开号：US20050182468A1

  公开（公告）日：2005-08-18

  Electrical devices (e.g., cardiac rhythm management and neurostimulation devices) for contact with tissue are used in combination with an anti-scarring agent (e.g., a cell cycle inhibitor) in order to inhibit scarring that may otherwise occur when the devices are implanted within an animal.

  用于与组织接触的电气设备（如心律管理和神经刺激设备）与抗疤痕剂（如细胞周期抑制剂）结合使用，以抑制设备植入动物体内时可能产生的疤痕。