1-(4-羟基-3-甲氧基-2-硝基苯基)乙酮 | 1260785-45-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-(4-羟基-3-甲氧基-2-硝基苯基)乙酮
• 中文别名: 2-硝基-4-羟基-3-甲氧基苯乙酮
• 英文名称: 1-(4-Hydroxy-3-methoxy-2-nitrophenyl)ethanone
• CAS: 1260785-45-2
• 化学式: C₉H₉NO₅
• 分子量: 211.174
• InChiKey: ZOMXLWJRXFETOW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  92.4
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 海关编码：
  2914700090
• 危险性防范说明：
  P261,P264,P270,P271,P280,P302+P352,P304+P340,P305+P351+P338,P312,P330,P362,P403+P233,P501
• 危险性描述：
  H302,H312,H332

反应信息

• 作为反应物：
  描述：

  1-(4-羟基-3-甲氧基-2-硝基苯基)乙酮 在 吡啶 、 三氯化铝 作用下， 以 1,2-二氯乙烷 为溶剂， 生成 3,4-dihydroxy-2-nitroacetophenone
  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
• 作为产物：
  描述：

  香草乙酮 在 吡啶 、 4-二甲氨基吡啶 、 sodium hydroxide 、 乙酸酐 、 copper(II) nitrate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 1-(4-羟基-3-甲氧基-2-硝基苯基)乙酮
  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

• 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.