N-Propanoyl-2-(2-methoxyphenyl)ethanamine | 111088-40-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: N-Propanoyl-2-(2-methoxyphenyl)ethanamine
• 英文别名: N-[2-(2-methoxyphenyl)ethyl]propanamide
• CAS: 111088-40-5
• 化学式: C₁₂H₁₇NO₂
• mdl: MFCD24388050
• 分子量: 207.272
• InChiKey: OKWSMTVSHNRDGG-UHFFFAOYSA-N

物化性质

• 熔点：
  46-47 °C(Solv: ethyl ether (60-29-7))
• 沸点：
  384.4±25.0 °C(Predicted)
• 密度：
  1.027±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.416
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-Propanoyl-2-(2-methoxyphenyl)ethanamine 在 三(三氟乙酸)碘 、 sodium bromide 作用下， 生成 Bis-[4-methoxy-3-(2-propionylamino-ethyl)-phenyl]-iodonium; bromide
  参考文献：
  名称：

  Thyroid hormone analogs. Synthesis of 3'-substituted 3,5-diiodo-L-thyronines and quantitative structure-activity studies of in vitro and in vivo thyromimetic activities in rat liver and heart

  摘要：

  Twenty-nine novel 3'-substituted derivatives of the thyroid hormone 3,3',5-triiodo-L-thyronine (T3) have been synthesized by using established methods and by a new route involving manipulation of a 3'-formyl intermediate. In vitro hormone receptor binding (to intact nuclei) and in vivo thyromimetic activity (induction of mitochondrial 3-phosphoglycerate oxidoreductase, GPDH) were measured in rat liver and heart for these new analogues and for the 18 previously reported 3'-substituted 3,5-diiodo-L-thyronines. Analysis of the binding data using theoretical conformational and quantitative structure-affinity methods implies that the 3'-substituent recognition site on the thyroid hormone receptor is hydrophobic and limited in depth to the length of the natural iodo substituent, but has sufficient width to accommodate a phenyl or cyclohexyl group. Receptor binding is reduced by approximately 10-fold in 3'-acyl derivatives which form strong intramolecular acceptor hydrogen bonds with the adjacent 4'-hydroxyl. The compounds studied showed no differences in their relative affinities for heart and liver nuclei, suggesting that receptors in these tissues are similar. However, the relationships between thyromimetic activity (induction of GPDH) and nuclear binding showed some tissue differences. A high correlation between activity and binding is observed for full agonists in the heart, but an equally significant correlation for the liver data is only seen when 3'-substituent bulk (molar refractivity) is included in the analysis. These results suggest the possibility that differential tissue penetration or access to receptors may occur in vivo.

  DOI：

  10.1021/jm00396a008
• 作为产物：
  描述：

  丙酸酐 、 2-甲氧基苯乙胺 在 sodium hydroxide 作用下， 反应 2.0h， 以85%的产率得到N-Propanoyl-2-(2-methoxyphenyl)ethanamine
  参考文献：
  名称：

  Thyroid hormone analogs. Synthesis of 3'-substituted 3,5-diiodo-L-thyronines and quantitative structure-activity studies of in vitro and in vivo thyromimetic activities in rat liver and heart

  摘要：

  Twenty-nine novel 3'-substituted derivatives of the thyroid hormone 3,3',5-triiodo-L-thyronine (T3) have been synthesized by using established methods and by a new route involving manipulation of a 3'-formyl intermediate. In vitro hormone receptor binding (to intact nuclei) and in vivo thyromimetic activity (induction of mitochondrial 3-phosphoglycerate oxidoreductase, GPDH) were measured in rat liver and heart for these new analogues and for the 18 previously reported 3'-substituted 3,5-diiodo-L-thyronines. Analysis of the binding data using theoretical conformational and quantitative structure-affinity methods implies that the 3'-substituent recognition site on the thyroid hormone receptor is hydrophobic and limited in depth to the length of the natural iodo substituent, but has sufficient width to accommodate a phenyl or cyclohexyl group. Receptor binding is reduced by approximately 10-fold in 3'-acyl derivatives which form strong intramolecular acceptor hydrogen bonds with the adjacent 4'-hydroxyl. The compounds studied showed no differences in their relative affinities for heart and liver nuclei, suggesting that receptors in these tissues are similar. However, the relationships between thyromimetic activity (induction of GPDH) and nuclear binding showed some tissue differences. A high correlation between activity and binding is observed for full agonists in the heart, but an equally significant correlation for the liver data is only seen when 3'-substituent bulk (molar refractivity) is included in the analysis. These results suggest the possibility that differential tissue penetration or access to receptors may occur in vivo.

  DOI：

  10.1021/jm00396a008

文献信息

• COMPOUNDS WHICH MODULATE THE CB2 RECEPTOR
  申请人：Bartolozzi Alessandra

  公开号：US20120316173A1

  公开（公告）日：2012-12-13

  Compounds of formula (I) are disclosed. Compounds according to the invention bind to and are agonists, antagonists or inverse agonists of the CB2 receptor, and are useful for treating inflammation. Those compounds which are agonists are additionally useful for treating pain.

  公式（I）的化合物已被揭示。本发明的化合物与CB2受体结合，并且是激动剂、拮抗剂或反向激动剂，可用于治疗炎症。那些是激动剂的化合物还可用于治疗疼痛。
• 2-Amido-8-methoxytetralins: A series of nonindolic melatonin-like agents
  作者：Swier Copinga、Pieter G. Tepper、Cor J. Grol、Alan S. Horn、Margarita L. Dubocovich

  DOI：10.1021/jm00072a008

  日期：1993.10

  A series of unsubstituted and methoxy-substituted 2-amidotetralins (4a-q) was prepared and evaluated for their ability to compete for 2-[I-125]iodomelatonin binding to chicken retinal membranes and for their potency to inhibit the calcium-dependent release of [H-3]dopamine from rabbit retina. The lead compound, 2-acetamido-8-methoxytetralin (4j), showed a moderate affinity (K(i) = 46 nM) and potency (IC50 = 1.4 nM) at the melatonin receptor. The structural requirements necessary for optimal agonistic activity at the melatonin receptor are as follows. First, the amido group, which should have a small, nonbranched alkyl group, is essential for affinity, and second, the methoxy substituent at the 8-position of the 2-amidotetralin ring is essential for optimal agonistic activity at the melatonin receptor. We concluded that this series of unsubstituted and methoxy-substituted 2-amidotetralins constitutes a class of nonindolic melatonin-like agents that can be used as pharmacological tools to further characterize melatonin receptors and to elucidate the mode of action of melatonin.
• An efficient sequence for the preparation of small secondary amine hydrochloride salts for focused library generation without need for distillation or chromatographic purification
  作者：Gene M. Dubowchik、Jodi A. Michne、Dmitry Zuev

  DOI：10.1016/j.bmcl.2004.04.014

  日期：2004.6

  Collections of small secondary amines for compound library generation can be efficiently prepared by amide reduction using BH(3)-THF or Red-Al followed by brief methanolysis, trapping with di-tert-butyl dicarbonate, and deprotection with 4M HCl in dioxane. The sequence requires no chromatography or distillation and provides multi-gram quantities of pure HCl salts in a short time.
• LEESON, PAUL D.;ELLIS, DAVID;EMMETT, JOHN C.;SHAH, VIRENDRA P.;SHOWELL, G+, J. MED. CHEM., 31,(1988) N 1, 37-54
  作者：LEESON, PAUL D.、ELLIS, DAVID、EMMETT, JOHN C.、SHAH, VIRENDRA P.、SHOWELL, G+

  DOI：——

  日期：——
• Thyroid hormone analogs. Synthesis of 3'-substituted 3,5-diiodo-L-thyronines and quantitative structure-activity studies of in vitro and in vivo thyromimetic activities in rat liver and heart
  作者：Paul D. Leeson、David Ellis、John C. Emmett、Virendra P. Shah、Graham A. Showell、Anthony H. Underwood

  DOI：10.1021/jm00396a008

  日期：1988.1

  Twenty-nine novel 3'-substituted derivatives of the thyroid hormone 3,3',5-triiodo-L-thyronine (T3) have been synthesized by using established methods and by a new route involving manipulation of a 3'-formyl intermediate. In vitro hormone receptor binding (to intact nuclei) and in vivo thyromimetic activity (induction of mitochondrial 3-phosphoglycerate oxidoreductase, GPDH) were measured in rat liver and heart for these new analogues and for the 18 previously reported 3'-substituted 3,5-diiodo-L-thyronines. Analysis of the binding data using theoretical conformational and quantitative structure-affinity methods implies that the 3'-substituent recognition site on the thyroid hormone receptor is hydrophobic and limited in depth to the length of the natural iodo substituent, but has sufficient width to accommodate a phenyl or cyclohexyl group. Receptor binding is reduced by approximately 10-fold in 3'-acyl derivatives which form strong intramolecular acceptor hydrogen bonds with the adjacent 4'-hydroxyl. The compounds studied showed no differences in their relative affinities for heart and liver nuclei, suggesting that receptors in these tissues are similar. However, the relationships between thyromimetic activity (induction of GPDH) and nuclear binding showed some tissue differences. A high correlation between activity and binding is observed for full agonists in the heart, but an equally significant correlation for the liver data is only seen when 3'-substituent bulk (molar refractivity) is included in the analysis. These results suggest the possibility that differential tissue penetration or access to receptors may occur in vivo.