N-(1,2,3,4-tetrahydro-8-methoxy-5-nitro-2-naphthalenyl) acetamide | 80270-85-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-(1,2,3,4-tetrahydro-8-methoxy-5-nitro-2-naphthalenyl) acetamide
• 英文别名: N-(1,2,3,4-tetrahydro-8-methoxy-5-nitro-2-naphthalenyl)-acetamide；N-(8-methoxy-5-nitro-1,2,3,4-tetrahydronaphthalen-2-yl)acetamide
• CAS: 80270-85-5
• 化学式: C₁₃H₁₆N₂O₄
• 分子量: 264.281
• InChiKey: LYGKODUFSTUJSY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  84.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(1,2,3,4-tetrahydro-8-methoxy-5-nitro-2-naphthalenyl) acetamide 在 platinum(IV) oxide 盐酸 、 氢气 、 diborane(6) 作用下， 以 四氢呋喃 为溶剂， 反应 9.5h， 生成 1,2,3,4-tetrahydro-N²-ethyl-8-methoxy-2,5-naphthalenediamine
  参考文献：
  名称：

  .alpha.-Adrenergic agents. 2. Synthesis and .alpha.1-agonist activity of 2-aminotetralins

  摘要：

  Substituted 2-aminotetralins are potent, selective, direct-acting agonists at postjunctional alpha 1 receptors. Within this series, substituent alterations on the ring, as well as on the nitrogen, change the potency of compounds by over three orders of magnitude (EC50 = 12 to greater than 10 000 nM). It has been demonstrated experimentally that substitution at both the 5 and 8 positions of the aromatic ring produces optimum agonist potency. Removal of either substituent results in a loss of potency and efficacy relative to norepinephrine. Substitution at positions 6 and/or 7 is generally detrimental to activity. Methyl, ethyl, or dimethyl substitution on nitrogen is compatible with high agonist potency, while substitution with larger groups is not. The most potent agonist in this series is 5-(thiomethyl)-8-methoxy-2-aminotetralin, which has an EC50 of 12 nM.

  DOI：

  10.1021/jm00344a009
• 作为产物：
  描述：

  8-甲氧基-1.2.3.4-四氢萘-2-胺 在 sodium hydroxide 、 三氟乙酸 、 sodium nitrite 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 N-(1,2,3,4-tetrahydro-8-methoxy-5-nitro-2-naphthalenyl) acetamide
  参考文献：
  名称：

  .alpha.-Adrenergic agents. 2. Synthesis and .alpha.1-agonist activity of 2-aminotetralins

  摘要：

  Substituted 2-aminotetralins are potent, selective, direct-acting agonists at postjunctional alpha 1 receptors. Within this series, substituent alterations on the ring, as well as on the nitrogen, change the potency of compounds by over three orders of magnitude (EC50 = 12 to greater than 10 000 nM). It has been demonstrated experimentally that substitution at both the 5 and 8 positions of the aromatic ring produces optimum agonist potency. Removal of either substituent results in a loss of potency and efficacy relative to norepinephrine. Substitution at positions 6 and/or 7 is generally detrimental to activity. Methyl, ethyl, or dimethyl substitution on nitrogen is compatible with high agonist potency, while substitution with larger groups is not. The most potent agonist in this series is 5-(thiomethyl)-8-methoxy-2-aminotetralin, which has an EC50 of 12 nM.

  DOI：

  10.1021/jm00344a009

文献信息

• 2-Aminotetralin compounds, pharmaceutical compositions and method of
  申请人：SmithKline Corporation

  公开号：US04320148A1

  公开（公告）日：1982-03-16

  2-Aminotetralin compounds having 5- and 8- substituents are centrally acting alpha.sub.1 agonists.

  具有5-和8-取代基的2-氨基四氢萘化合物是中枢作用的α1激动剂。
• Hexa-cyclic compound
  申请人：DAIICHI PHARMACEUTICAL CO., LTD.

  公开号：EP0495432B1

  公开（公告）日：1996-05-29
• DEMARINIS, R. M.;SHAH, D. H.;HALL, R. F.;HIEBLE, J. P.;PENDLETON, R. G., J. MED. CHEM., 1982, 25, N 2, 136-141
  作者：DEMARINIS, R. M.、SHAH, D. H.、HALL, R. F.、HIEBLE, J. P.、PENDLETON, R. G.

  DOI：——

  日期：——
• 2-Aminotetralin compounds and pharmaceutical compositions having central alpha1 agonist activity
  申请人：SMITHKLINE BECKMAN CORPORATION

  公开号：EP0052932B1

  公开（公告）日：1984-02-22
• US4320148A
  申请人：——

  公开号：US4320148A

  公开（公告）日：1982-03-16