1-吗啉-4-基-2-四氢萘-2-基-乙硫酮 | 5452-58-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 中文名称: 1-吗啉-4-基-2-四氢萘-2-基-乙硫酮
• 英文名称: 1-morpholin-4-yl-2-(5,6,7,8-tetrahydronaphthalen-2-yl)-ethanethione
• 英文别名: 4-[(5,6,7,8-tetrahydro-[2]naphthyl)-thioacetyl]-morpholine；4-[(5,6,7,8-Tetrahydro-[2]naphthyl)-thioacetyl]-morpholin；4-((5,6,7,8-Tetrahydro-2-naphthyl)thioacetyl)morpholine；1-morpholin-4-yl-2-(5,6,7,8-tetrahydronaphthalen-2-yl)ethanethione
• CAS: 5452-58-4
• 化学式: C₁₆H₂₁NOS
• 分子量: 275.415
• InChiKey: RRHRCKOVXFVNDU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  44.6
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  1-吗啉-4-基-2-四氢萘-2-基-乙硫酮 在 氢氧化钾 作用下， 反应 20.0h， 以75%的产率得到5,6,7,8-四氢萘-2-乙酸
  参考文献：
  名称：

  Selective .kappa.-Opioid Agonists: Synthesis and Structure-Activity Relationships of Piperidines Incorporating an Oxo-Containing Acyl Group

  摘要：

  This study describes the synthesis and the structure-activity relationships (SARs) of the (S)-(-)-enantiomers of a novel class of 2-(aminomethyl)piperidine derivatives, using K-opioid binding affinity and antinociceptive potency as the indices of biological activity. Compounds incorporating the 1-tetralon-6-ylacetyl residue (30 and 34-45) demonstrated an in vivo antinociceptive activity greater than predicted on the basis of their kappa-binding affinities. In particular, (2S)-2-[(dimethylamino)methyl]-1-[(5,6,7,8-tetrahydro-5-oxo-2-naphthyl)acetyl]piperidine (34) was found to have a potency similar to spiradoline in animal models of antinociception after subcutaneous administration, with ED(50)s of 0.47 and 0.73 mu mol/kg in the mouse and in the rat abdominal constriction tests, respectively. Further in vivo studies in mice and/or rats revealed that compound 34, compared to other selective K-agonists, has a reduced propensity to cause a number of K-related side effects, including locomotor impairment/sedation and diuresis, at antinociceptive doses. For example, it has an ED(50) Of 26.5 mu mol/kg sc in the rat rotarod model, exhibiting a ratio of locomotor impairment/sedation vs analgesia of 36. Possible reasons for this differential activity and its clinical consequence are discussed.

  DOI：

  10.1021/jm00047a006
• 作为产物：
  描述：

  1,2,3,4-四氢萘 、 alkaline earth salt of/the/ methylsulfuric acid 在 三氯化铝 、 sulfur 作用下， 以 二氯甲烷 为溶剂， 反应 39.0h， 生成 1-吗啉-4-基-2-四氢萘-2-基-乙硫酮
  参考文献：
  名称：

  Selective .kappa.-Opioid Agonists: Synthesis and Structure-Activity Relationships of Piperidines Incorporating an Oxo-Containing Acyl Group

  摘要：

  This study describes the synthesis and the structure-activity relationships (SARs) of the (S)-(-)-enantiomers of a novel class of 2-(aminomethyl)piperidine derivatives, using K-opioid binding affinity and antinociceptive potency as the indices of biological activity. Compounds incorporating the 1-tetralon-6-ylacetyl residue (30 and 34-45) demonstrated an in vivo antinociceptive activity greater than predicted on the basis of their kappa-binding affinities. In particular, (2S)-2-[(dimethylamino)methyl]-1-[(5,6,7,8-tetrahydro-5-oxo-2-naphthyl)acetyl]piperidine (34) was found to have a potency similar to spiradoline in animal models of antinociception after subcutaneous administration, with ED(50)s of 0.47 and 0.73 mu mol/kg in the mouse and in the rat abdominal constriction tests, respectively. Further in vivo studies in mice and/or rats revealed that compound 34, compared to other selective K-agonists, has a reduced propensity to cause a number of K-related side effects, including locomotor impairment/sedation and diuresis, at antinociceptive doses. For example, it has an ED(50) Of 26.5 mu mol/kg sc in the rat rotarod model, exhibiting a ratio of locomotor impairment/sedation vs analgesia of 36. Possible reasons for this differential activity and its clinical consequence are discussed.

  DOI：

  10.1021/jm00047a006

文献信息

• Synthetic Studies in the Isoquinoline Series
  作者：Everett M. Schultz、R. T. Arnold

  DOI：10.1021/ja01174a003

  日期：1949.6
• Applicability of Stand Structural Characteristics to Stemflow Modeling
  作者：Ho-Taek Park、Shigeaki Hattori

  DOI：10.1007/bf02762513

  日期：2002.5
• WILLGERODT-KINDLER'S MICROWAVE-ENHANCED SYNTHESIS OF THIOAMIDE DERIVATIVES
  作者：Jacques H. Poupaert、Sandro Duarte、Evelina Colacino、Patrick Depreux、Christopher R. McCurdy、Didier L. Lambert

  DOI：10.1080/10426500490466995

  日期：2004.10.1

  The Willgerodt-Kindler reaction was applied to a series of aromatic aldehydes and ketones. The reactions were performed in a dipolar aprotic solvent (mainly DMF) in the presence of a base catalyst (4-methylmorpholine) and utilized microwave (mw) irradiation. The pulsed mw technique rather than the continuous irradiation was preferred because it limited side reactions and hydrogen sulfide production. While not always superior to the thermal activation of the reaction, the procedure involving repetitive short pulses of microwave irradiation was found to be faster and result in consistently cleaner products. The technique can be easily applied in a fast parallel synthesis process.