6-benzyloxy-7-hydroxy-8-nitro-1-tetralone | 383383-11-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 6-benzyloxy-7-hydroxy-8-nitro-1-tetralone
• 英文别名: 7-hydroxy-8-nitro-6-phenylmethoxy-3,4-dihydro-2H-naphthalen-1-one
• CAS: 383383-11-7
• 化学式: C₁₇H₁₅NO₅
• 分子量: 313.31
• InChiKey: XGHZDOZGJYGDSJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  92.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-benzyloxy-7-hydroxy-8-nitro-1-tetralone 生成 6,7-dihydroxy-8-nitro-3,4-dihydro-2H-naphthalen-1-one
  参考文献：
  名称：

  Substituted nitrated catechols, their use in the treatment of some central and peripheral nervous system disorders and pharmaceutical compositions containing them

  摘要：

  公式I的新化合物被描述如下： 这些化合物在治疗一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。

  公开号：

  EP1167341A1
• 作为产物：
  描述：

  6,7-二羟基-3,4-二氢-1(2H)-萘酮 在 硝酸 、 potassium carbonate 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.67h， 生成 6-benzyloxy-7-hydroxy-8-nitro-1-tetralone
  参考文献：
  名称：

  Synthesis and Biological Evaluation of a Novel Series of “Ortho-Nitrated” Inhibitors of Catechol-O-methyltransferase

  摘要：

  Novel regioisomeric "ortho-nitrated" catechols related to the catechol-O-methyltransferase (COMT) inhibitors BIA 3-202 3 and BIA 3-335 4 were synthesized and biologically evaluated. Changing the position of the nitro group from the "classical" meta- to the ortho-position relative to the side-chain substituent of the nitrocatechol pharmacophore exerted profound effects on selectivity and duration of COMT inhibition. Alkylaryl compounds 7a-d possessed shorter duration of action than their regioisomers, but 7b displayed reversed selectivity over 3 at 3 and 6 h, exhibiting preferential central inhibition. In the amino-substituted series, ortho-nitrated regioisomer 14k was less peripherally selective than 4 and short-acting, whereas decahydroquinoline 14g displayed an unprecedented combination of long-acting and selective peripheral inhibition. 7b could provide a useful tool to probe the pharmacological utility of short-acting, centrally selective COMT inhibitors in the treatment of depression in Parkinsonian patients, and 14g represents a promising candidate for clinical evaluation as an adjunct to L-Dopa therapy.

  DOI：

  10.1021/jm0580454

文献信息

• Substituted nitrated catechols, their use in the treatment of some central and peripheral nervous system disorders and pharmaceutical compositions containing them
  申请人：Portela & Ca., S.A.

  公开号：EP1167341A1

  公开（公告）日：2002-01-02

  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.

  公式I的新化合物被描述如下： 这些化合物在治疗一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。
• Synthesis and Biological Evaluation of a Novel Series of “Ortho-Nitrated” Inhibitors of Catechol-<i>O</i>-methyltransferase
  作者：David A. Learmonth、Maria João Bonifácio、Patrício Soares-da-Silva

  DOI：10.1021/jm0580454

  日期：2005.12.1

  Novel regioisomeric "ortho-nitrated" catechols related to the catechol-O-methyltransferase (COMT) inhibitors BIA 3-202 3 and BIA 3-335 4 were synthesized and biologically evaluated. Changing the position of the nitro group from the "classical" meta- to the ortho-position relative to the side-chain substituent of the nitrocatechol pharmacophore exerted profound effects on selectivity and duration of COMT inhibition. Alkylaryl compounds 7a-d possessed shorter duration of action than their regioisomers, but 7b displayed reversed selectivity over 3 at 3 and 6 h, exhibiting preferential central inhibition. In the amino-substituted series, ortho-nitrated regioisomer 14k was less peripherally selective than 4 and short-acting, whereas decahydroquinoline 14g displayed an unprecedented combination of long-acting and selective peripheral inhibition. 7b could provide a useful tool to probe the pharmacological utility of short-acting, centrally selective COMT inhibitors in the treatment of depression in Parkinsonian patients, and 14g represents a promising candidate for clinical evaluation as an adjunct to L-Dopa therapy.