8-Chloro-5-methoxy-1,2,3,4-tetrahydro-naphthalene-2-carboxylic acid | 80270-87-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 8-Chloro-5-methoxy-1,2,3,4-tetrahydro-naphthalene-2-carboxylic acid
• 英文别名: 8-Chloro-5-methoxy-1,2,3,4-tetrahydronaphthalene-2-carboxylic acid
• CAS: 80270-87-7
• 化学式: C₁₂H₁₃ClO₃
• 分子量: 240.686
• InChiKey: IFMYYPAUGBOFKG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  8-Chloro-5-methoxy-1,2,3,4-tetrahydro-naphthalene-2-carboxylic acid 在 氯化亚砜 、 sodium azide 作用下， 以 水 、 丙酮 、 甲苯 为溶剂， 反应 3.33h， 生成 1,2,3,4-tetrahydro-8-chloro-5-methoxy-2-naphthalenamine
  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-Chloro-5-methoxy-3,4-dihydro-naphthalene-2-carboxylic acid ethyl ester 在 platinum(IV) oxide sodium hydroxide 、 氢气 作用下， 以 乙醇 为溶剂， 反应 8.0h， 生成 8-Chloro-5-methoxy-1,2,3,4-tetrahydro-naphthalene-2-carboxylic acid
  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

• 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：——
• .alpha.-Adrenergic agents. 2. Synthesis and .alpha.1-agonist activity of 2-aminotetralins
  作者：R. M. DeMarinis、D. H. Shah、R. F. Hall、J. P. Hieble、R. G. Pendleton

  DOI：10.1021/jm00344a009

  日期：1982.2

  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.