1-(2-benzyloxy-6-methoxy-phenyl)-ethanone | 93434-28-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(2-benzyloxy-6-methoxy-phenyl)-ethanone
• 英文别名: 1-(2-Benzyloxy-6-methoxy-phenyl)-aethanon；2-Benzyloxy-6-methoxy-acetophenon；Populneyl-methylaether；2-Benzyl-Oxy-6-Methoxyacetophenone；1-(2-methoxy-6-phenylmethoxyphenyl)ethanone
• CAS: 93434-28-7
• 化学式: C₁₆H₁₆O₃
• 分子量: 256.301
• InChiKey: VVHZHWVKKLSRCQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(2-benzyloxy-6-methoxy-phenyl)-ethanone 在 palladium on activated charcoal 盐酸 、 ammonium acetate 、 氢气 、 溶剂黄146 作用下， 以 1,4-二氧六环 、 乙酸乙酯 为溶剂， 20.0~120.0 ℃ 、303.98 kPa 条件下， 生成 2'-Amino-6'-(2-hydroxy-6-methoxy-phenyl)-1,2,3,4,5,6-hexahydro-[3,4']bipyridinyl-3'-carbonitrile
  参考文献：
  名称：

  Synthesis and structure–activity relationships of novel IKK-β inhibitors. Part 3: Orally active anti-inflammatory agents

  摘要：

  A series of 2-amino-3-cyano-4-alkyl-6-(2-hydroxyphenyl)pyridine derivatives was synthesized and evaluated as IkappaB kinase beta (IKK-beta) inhibitors. Modification of a novel IKK-beta inhibitor 1 (IKK-beta IC50 = 1500 nM, Cell IC50 = 8000 nM) at the 4-phenyl ring and 6-phenol group on the pyridine core ring resulted in a marked increased in biological activities. An optimized compound, 2-amino-6-[2-(cyclopropylmethoxy)-6-hydroxyphenyl]-4-piperidin-4-yl nicotinonitrile, exhibited excellent in vitro profiles (IKK-beta IC50 = 8.5 nM, Cell IC50 = 60 nM) and a strong oral efficacy in in vivo anti-inflammatory assays (significant effects at 1 mg/kg, po in arachidonic acid-induced ear edema model in mice). (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.05.041
• 作为产物：
  描述：

  1-(2-羟基-6-甲氧基苯基)乙基-1-酮 、 溴甲苯 在 potassium carbonate 、 sodium iodide 作用下， 以 丙酮 为溶剂， 生成 1-(2-benzyloxy-6-methoxy-phenyl)-ethanone
  参考文献：
  名称：

  Synthesis and structure–activity relationships of novel IKK-β inhibitors. Part 3: Orally active anti-inflammatory agents

  摘要：

  A series of 2-amino-3-cyano-4-alkyl-6-(2-hydroxyphenyl)pyridine derivatives was synthesized and evaluated as IkappaB kinase beta (IKK-beta) inhibitors. Modification of a novel IKK-beta inhibitor 1 (IKK-beta IC50 = 1500 nM, Cell IC50 = 8000 nM) at the 4-phenyl ring and 6-phenol group on the pyridine core ring resulted in a marked increased in biological activities. An optimized compound, 2-amino-6-[2-(cyclopropylmethoxy)-6-hydroxyphenyl]-4-piperidin-4-yl nicotinonitrile, exhibited excellent in vitro profiles (IKK-beta IC50 = 8.5 nM, Cell IC50 = 60 nM) and a strong oral efficacy in in vivo anti-inflammatory assays (significant effects at 1 mg/kg, po in arachidonic acid-induced ear edema model in mice). (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.05.041

文献信息

• Heterocyclic compounds for treating hepatitis C virus
  申请人：Vourloumis Dionisios

  公开号：US20050075375A1

  公开（公告）日：2005-04-07

  The invention is directed to heterocyclic compounds and pharmaceutical compositions of the same for treating Hepatitis C virus.

  这项发明涉及杂环化合物和其制备的药物组合物，用于治疗丙型肝炎病毒。
• 258. Derivatives of 5 : 6 : 4′- and 5 : 8 : 4′-trihydroxyflavones, and a note on the structure of ginkgetin
  作者：Wilson Baker、W. H. C. Simmonds

  DOI：10.1039/jr9400001370

  日期：——
• [EN] HETEROCYCLIC COMPOUNDS FOR TREATING HEPATITIS C VIRUS<br/>[FR] COMPOSES HETEROCYCLIQUES POUR TRAITER LE VIRUS DE L'HEPATITE C
  申请人：ANADYS PHARMACEUTICALS INC

  公开号：WO2004110351A2

  公开（公告）日：2004-12-23

  The invention is directed to heterocyclic compounds and pharmaceutical compositions of the same for treating Hepatitis C virus.
• Synthesis and structure–activity relationships of novel IKK-β inhibitors. Part 3: Orally active anti-inflammatory agents
  作者：Toshiki Murata、Mitsuyuki Shimada、Sachiko Sakakibara、Takashi Yoshino、Tsutomu Masuda、Takuya Shintani、Hiroki Sato、Yuji Koriyama、Keiko Fukushima、Noriko Nunami、Megumi Yamauchi、Kinji Fuchikami、Hiroshi Komura、Akihiko Watanabe、Karl B Ziegelbauer、Kevin B Bacon、Timothy B Lowinger

  DOI：10.1016/j.bmcl.2004.05.041

  日期：2004.8

  A series of 2-amino-3-cyano-4-alkyl-6-(2-hydroxyphenyl)pyridine derivatives was synthesized and evaluated as IkappaB kinase beta (IKK-beta) inhibitors. Modification of a novel IKK-beta inhibitor 1 (IKK-beta IC50 = 1500 nM, Cell IC50 = 8000 nM) at the 4-phenyl ring and 6-phenol group on the pyridine core ring resulted in a marked increased in biological activities. An optimized compound, 2-amino-6-[2-(cyclopropylmethoxy)-6-hydroxyphenyl]-4-piperidin-4-yl nicotinonitrile, exhibited excellent in vitro profiles (IKK-beta IC50 = 8.5 nM, Cell IC50 = 60 nM) and a strong oral efficacy in in vivo anti-inflammatory assays (significant effects at 1 mg/kg, po in arachidonic acid-induced ear edema model in mice). (C) 2004 Elsevier Ltd. All rights reserved.