1-(4-benzyloxy-3-methoxyphenyl)-2-phenyl-ethanol | 274925-95-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 1-(4-benzyloxy-3-methoxyphenyl)-2-phenyl-ethanol
• 英文别名: 1-(4-Benzyloxy-3-methoxyphenyl)-2-phenyl-1-ethanol；1-(3-methoxy-4-phenylmethoxyphenyl)-2-phenylethanol
• CAS: 274925-95-0
• 化学式: C₂₂H₂₂O₃
• 分子量: 334.415
• InChiKey: NPTQBIXTBGWTFK-UHFFFAOYSA-N

物化性质

• 熔点：
  96-98 °C
• 沸点：
  480.0±45.0 °C(Predicted)
• 密度：
  1.153±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(4-benzyloxy-3-methoxyphenyl)-2-phenyl-ethanol 在 10percent Pd/C 吡啶 、 三氯化铝 、 ammonium formate 、 环己酮 、 溶剂黄146 、 sodium t-butanolate 作用下， 以 甲醇 、 乙酸乙酯 、 甲苯 为溶剂， 反应 3.5h， 生成 3-硝基-5-苯基乙酰基邻苯二酚
  参考文献：
  名称：

  Synthesis of 1-(3,4-Dihydroxy-5-nitrophenyl)-2-phenyl-ethanone and Derivatives as Potent and Long-Acting Peripheral Inhibitors of Catechol-O-methyltransferase

  摘要：

  A homologous series of novel nitro-catechol structures (7a-7e) were synthesized and tested as inhibitors of the enzyme catechol-O-methyltransferase (COMT). Increasing chain length was found to have significant impact on both brain penetration and duration of COMT inhibition in the rat. Of this series, compound 7b (1-(3,4-dihydroxy-5-nitrophenyl)-2-phenyl-ethanone) was found to exhibit the most potent and selective inhibition of peripheral COMT, with an inhibition profile more similar to entacapone 2 than tolcapone 1 (an equipotent peripheral and central inhibitor) but with much improved duration of action (7b, 70% inhibition and 2, 25% inhibition at 9 h after administration). The effects of structural modifications to 7b on COMT inhibitory profile were investigated, and it is concluded that the carbonyl group and preferably unsubstituted aromatic ring are essential features to maintain prolonged peripheral COMT inhibition. The introduction of the alpha-methylene group, the major structural difference between 7b and 1, would appear responsible for the observed enhancement in selectivity of peripheral COMT inhibition of 7b, which has more limited access to the brain than 1.

  DOI：

  10.1021/jm0109964
• 作为产物：
  描述：

  4-苄氧基-3-甲氧基苯甲醛 以93的产率得到1-(4-benzyloxy-3-methoxyphenyl)-2-phenyl-ethanol
  参考文献：
  名称：

  J. Med. Chem. 2002, 45, 685-695

  摘要：

  DOI：

文献信息

• Substituted 2-phenyl-1-(3,4-dihydroxy-5-nitrophenyl)-1-ethanones, their use in the treatment of some central and peripheral nervous system disorders and pharmaceutical compositions containing them
  申请人：Portela & C.A., S.A.

  公开号：US06512136B1

  公开（公告）日：2003-01-28

  New compounds of formula I are described The compounds have potentially valuable pharmaceutical properties in the treatment of some central and peripheral nervous system disorders, where a reduction in the O-methylation of catecholamines may be of therapeutical benefit, such as Parkinson's disease and parkinsonian disorders, gastrointestinal disturbances, edema formation states and hypertension.

  公式I的新化合物被描述。这些化合物在治疗某些中枢和外周神经系统疾病中具有潜在的有价值的药理特性，其中对儿茶酚胺的O-甲基化减少可能具有治疗效果，比如帕金森病和帕金森综合征、胃肠道紊乱、水肿和高血压。
• IMPROVED METHOD FOR DEMETHYLATION OF NITRO- CATECHOL METHYL ETHERS
  作者：David A. Learmonth、Paula C. Alves

  DOI：10.1081/scc-120002413

  日期：2002.1.1

  Several nitro-catechol compounds. useful as inhibitors of COMT were obtained in excellent yield and purity via an improved procedure for demethylation of the corresponding methyl ethers using aluminium chloride and pyridine in ethyl acetate.
• US6512136B1
  申请人：——

  公开号：US6512136B1

  公开（公告）日：2003-01-28
• Synthesis of 1-(3,4-Dihydroxy-5-nitrophenyl)-2-phenyl-ethanone and Derivatives as Potent and Long-Acting Peripheral Inhibitors of Catechol-<i>O</i>-methyltransferase
  作者：David A. Learmonth、Maria A. Vieira-Coelho、Jan Benes、Paula C. Alves、Nuno Borges、Ana P. Freitas、Patrício Soares-da-Silva

  DOI：10.1021/jm0109964

  日期：2002.1.1

  A homologous series of novel nitro-catechol structures (7a-7e) were synthesized and tested as inhibitors of the enzyme catechol-O-methyltransferase (COMT). Increasing chain length was found to have significant impact on both brain penetration and duration of COMT inhibition in the rat. Of this series, compound 7b (1-(3,4-dihydroxy-5-nitrophenyl)-2-phenyl-ethanone) was found to exhibit the most potent and selective inhibition of peripheral COMT, with an inhibition profile more similar to entacapone 2 than tolcapone 1 (an equipotent peripheral and central inhibitor) but with much improved duration of action (7b, 70% inhibition and 2, 25% inhibition at 9 h after administration). The effects of structural modifications to 7b on COMT inhibitory profile were investigated, and it is concluded that the carbonyl group and preferably unsubstituted aromatic ring are essential features to maintain prolonged peripheral COMT inhibition. The introduction of the alpha-methylene group, the major structural difference between 7b and 1, would appear responsible for the observed enhancement in selectivity of peripheral COMT inhibition of 7b, which has more limited access to the brain than 1.
• J. Med. Chem. 2002, 45, 685-695
  作者：

  DOI：——

  日期：——