(+/-)-5-methoxy-1,2,3,4-tetrahydro-1-naphthaleneacetic acid | 214908-27-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: (+/-)-5-methoxy-1,2,3,4-tetrahydro-1-naphthaleneacetic acid
• 英文别名: (5-methoxy-1,2,3,4-tetrahydro-[1]naphthyl)-acetic acid；(5-Methoxy-1,2,3,4-tetrahydro-[1]naphthyl)-essigsaeure；2-(5-Methoxy-1,2,3,4-tetrahydronaphthalen-1-yl)acetic acid
• CAS: 214908-27-7
• 化学式: C₁₃H₁₆O₃
• 分子量: 220.268
• InChiKey: HUSQUBKEKXHDJY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 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：

  (+/-)-5-methoxy-1,2,3,4-tetrahydro-1-naphthaleneacetic acid 在 氯化亚砜 、 三乙胺 作用下， 生成 ((S)-5-Methoxy-1,2,3,4-tetrahydro-naphthalen-1-yl)-acetyl chloride
  参考文献：
  名称：

  1-Aryl-4-[(5-methoxy-1,2,3,4-tetrahydronaphthalen-1-yl)alkyl]piperazines and Their Analogues:  Influence of the Stereochemistry of the Tetrahydronaphthalen-1-yl Nucleus on 5-HT_1A Receptor Affinity and Selectivity versus α₁ and D₂ Receptors. 5

  摘要：

  Some 1-aryl-4-[(5-methoxy-1,2,3,4-tetrahydronaphthalen-1-yl)-n-propyl]piperazines and their alkylamino and alkylamido analogues, previously studied as 5-HT1A ligands, were prepared in enantiomerically pure form, and their absolute configuration was det;ermined by chemical correlation or by chiroptical properties. They were evaluated for in vitro 5-HT1A, D-2, and alpha(1) receptor affinity by radioligand binding assays, to study the influence of the chiral carbon atom of the tetrahydronaphthalene nucleus on the 5-HT1A affinity and selectivity. Results indicated that, as regarding the 5-HT1A receptor affinity, there was no difference in affinity between (-)- and (+)-enantiomers as well as the racemate of each compound. The stereochemistry, instead, influenced the selectivity: all (-)-enantiomers displayed affinity values higher than those of (+)-isomers at D-2 receptors, and conversely, all (+)-enantiomers displayed affinity values higher than those of (-)-isomers at alpha(1) receptors. As a result of this trend, it is not possible to predict the isomer with a better selectivity profile. However, compounds (S)-(+)-2, (S)-(+)-4, and (R)-(+)-6 displayed high affinity for the 5-HT1A receptor (IC50 values ranging between 7.0 and 2.3 nM) and good selectivity (greater than or equal to 250-fold) versus both D-2 and alpha(1) receptors. Furthermore, compounds (S)-(+)-4 and (R)-(-)-4 were submitted to the [S-35]GTP gamma S binding assay for a preliminary evaluation of their intrinsic activity on the 5-HT1A receptor.

  DOI：

  10.1021/jm980420n
• 作为产物：
  描述：

  Ethyl-5-methoxy-1.2.3.4-tetrahydronaphthalen-1-acetat 在 sodium hydroxide 作用下， 生成 (+/-)-5-methoxy-1,2,3,4-tetrahydro-1-naphthaleneacetic acid
  参考文献：
  名称：

  3,3-二甲基哌啶的N-ω-（Tetralin-1-yl）烷基]衍生物是高效且选择性的sigma1或sigma2配体。

  摘要：

  制备了几种3，3-二甲基-N-ω-（四氢萘-1-基）烷基]哌啶衍生物和一些相关化合物。通过放射性配体结合试验研究了它们的亲和力和sigma亚型选择性，用[3H] -SKF 10047标记了sigma1受体，并用[3H] -DTG标记了sigma2受体。许多测试的化合物以纳摩尔或亚纳摩尔IC50值结合sigma1和/或sigma2受体。化合物（+）-22，（+）-3,3-二甲基-1- [3-（5-甲氧基-1,2,3,4-四氢萘-1-基）-正丙基]哌啶是最有效的（IC50 = 0.089 nM）和选择性的sigma1配体（1340倍），显示出10倍的对映选择性。化合物29（3，3-二甲基-1- [4-（6-甲氧基-1,2,3，4-四氢萘-1-基）-正丁基]哌啶）和31（3，3-二甲基-1 -[5-（1,2,3，4-四氢萘-1-基）-正戊基]哌啶）的效力很高（IC50 = 0。

  DOI：

  10.1021/jm970692a

文献信息

• NAPHTHALENE DERIVATIVES AS PROSTAGLANDIN I2 AGONISTS
  申请人：FUJISAWA PHARMACEUTICAL CO., LTD.

  公开号：EP0749424B1

  公开（公告）日：2001-09-12
• US5763489A
  申请人：——

  公开号：US5763489A

  公开（公告）日：1998-06-09
• US5863918A
  申请人：——

  公开号：US5863918A

  公开（公告）日：1999-01-26
• 1-Aryl-4-[(5-methoxy-1,2,3,4-tetrahydronaphthalen-1-yl)alkyl]piperazines and Their Analogues:  Influence of the Stereochemistry of the Tetrahydronaphthalen-1-yl Nucleus on 5-HT_1A Receptor Affinity and Selectivity versus α₁ and D₂ Receptors. 5
  作者：Roberto Perrone、Francesco Berardi、Nicola A. Colabufo、Marcello Leopoldo、Vincenzo Tortorella

  DOI：10.1021/jm980420n

  日期：1999.2.1

  Some 1-aryl-4-[(5-methoxy-1,2,3,4-tetrahydronaphthalen-1-yl)-n-propyl]piperazines and their alkylamino and alkylamido analogues, previously studied as 5-HT1A ligands, were prepared in enantiomerically pure form, and their absolute configuration was det;ermined by chemical correlation or by chiroptical properties. They were evaluated for in vitro 5-HT1A, D-2, and alpha(1) receptor affinity by radioligand binding assays, to study the influence of the chiral carbon atom of the tetrahydronaphthalene nucleus on the 5-HT1A affinity and selectivity. Results indicated that, as regarding the 5-HT1A receptor affinity, there was no difference in affinity between (-)- and (+)-enantiomers as well as the racemate of each compound. The stereochemistry, instead, influenced the selectivity: all (-)-enantiomers displayed affinity values higher than those of (+)-isomers at D-2 receptors, and conversely, all (+)-enantiomers displayed affinity values higher than those of (-)-isomers at alpha(1) receptors. As a result of this trend, it is not possible to predict the isomer with a better selectivity profile. However, compounds (S)-(+)-2, (S)-(+)-4, and (R)-(+)-6 displayed high affinity for the 5-HT1A receptor (IC50 values ranging between 7.0 and 2.3 nM) and good selectivity (greater than or equal to 250-fold) versus both D-2 and alpha(1) receptors. Furthermore, compounds (S)-(+)-4 and (R)-(-)-4 were submitted to the [S-35]GTP gamma S binding assay for a preliminary evaluation of their intrinsic activity on the 5-HT1A receptor.
• <i>N</i>-[ω-(Tetralin-1-yl)alkyl] Derivatives of 3,3-Dimethylpiperidine Are Highly Potent and Selective σ₁ or σ₂ Ligands
  作者：Francesco Berardi、Sergio Santoro、Roberto Perrone、Vincenzo Tortorella、Stefano Govoni、Laura Lucchi

  DOI：10.1021/jm970692a

  日期：1998.10.1

  089 nM) and selective sigma1 ligand (1340-fold), showing a 10-fold enantioselectivity. Compounds 29 (3, 3-dimethyl-1-[4-(6-methoxy-1,2,3, 4-tetrahydronaphthalen-1-yl)-n-butyl]piperidine) and 31 (3, 3-dimethyl-1-[5-(1,2,3, 4-tetrahydronaphthalen-1-yl)-n-pentyl]piperidine) were highly potent (IC50 = 0.016 nM and IC50 = 0.008 nM, respectively) and highly selective sigma2 ligands (more than 100000-fold)

  制备了几种3，3-二甲基-N-ω-（四氢萘-1-基）烷基]哌啶衍生物和一些相关化合物。通过放射性配体结合试验研究了它们的亲和力和sigma亚型选择性，用[3H] -SKF 10047标记了sigma1受体，并用[3H] -DTG标记了sigma2受体。许多测试的化合物以纳摩尔或亚纳摩尔IC50值结合sigma1和/或sigma2受体。化合物（+）-22，（+）-3,3-二甲基-1- [3-（5-甲氧基-1,2,3,4-四氢萘-1-基）-正丙基]哌啶是最有效的（IC50 = 0.089 nM）和选择性的sigma1配体（1340倍），显示出10倍的对映选择性。化合物29（3，3-二甲基-1- [4-（6-甲氧基-1,2,3，4-四氢萘-1-基）-正丁基]哌啶）和31（3，3-二甲基-1 -[5-（1,2,3，4-四氢萘-1-基）-正戊基]哌啶）的效力很高（IC50 = 0。